Wolford v. United States (722 F. Supp. 2d 664, 2010)

MEMORANDUM OPINION

T.S. ELLIS, III, District Judge.

Following a six-day jury trial, petitioner, Sharon Raedelle Wolford (“Wolford”), was convicted of one count of conspiracy to distribute oxycodone and other controlled substances within 1,000 feet of an elementary school, in violation of 21 U.S.C. §§ 841(a), 846 and 860, and two substantive counts of distributing oxycodone, in violation of 21 U.S.C. § 841(a). She was ultimately sentenced to concurrent terms of imprisonment of 108 months as to each of the three counts of conviction — a significant downward variance from the applicable guidelines range of imprisonment of 360 months to life.

Now at issue is Wolford’s motion to vacate, set aside or correct her convictions and sentence, pursuant to 28 U.S.C. § 2255, based primarily on the alleged ineffective assistance of her appointed counsel in the plea negotiation and pretrial proceedings. Counsel for both Wolford and the government have fully briefed the issues raised in the instant motion and an evidentiary hearing was held in accordance with § 2255(b), which provides that “[u]n-less the motion and the files and records of the case conclusively show that the prisoner is entitled to no relief, the court shall ... grant a prompt hearing thereon.... ” 28 U.S.C. § 2255(b). Oral argument was heard in the course of the evidentiary hearing and additional oral argument is unnecessary as the facts and legal contentions are adequately set forth in the existing record.

I.

Resolution of the questions presented requires a detailed, chronological summary of the pertinent facts and procedural history.

This prosecution was initiated on February 22, 2006, with the issuance of a federal criminal complaint charging Wolford with one count of conspiracy to distribute cocaine, oxycodone, dextroamphetamine and methadone in the Eastern District of Virginia, in violation of 21 U.S.C. §§ 841(a)(1) and 846. The criminal complaint also charged several alleged co-conspirators, including (i) Wolford’s son, Christopher Wolford, and (ii) Wolford’s former live-in boyfriend, William McCauley. In essence, the criminal complaint charged Wolford and her alleged co-conspirators with operating a lengthy drug distribution enterprise — from 2001 to 2006 — out of Wolford’s primary residence, which was located within 1,000 feet of an elementary school in Manassas, Virginia. The majority of the controlled substances involved in the charged conspiracy were pain medications obtained by Wolford and McCauley through the use of physician-issued medical prescriptions. And, although many of these controlled substances were indeed distributed or sold to others, or traded with others in exchange for different types of drugs, the record reflects that significant quantities of the controlled substances were also used personally by Wolford and McCauley, as both were addicted to prescription pain killers.

Wolford was arrested on the criminal complaint on February 23, 2006, and her residence was searched pursuant to a search warrant later that day. In the course of the search, federal agents seized, inter alia, (i) nearly one hundred empty prescription bottles for various controlled substances that had been prescribed to Wolford, McCauley and other unindicted co-conspirators, totaling more than 8,000 pills, (ii) drug measuring devices, (iii) syringes, spoons and drug pipes with suspected drug residue, and (iv) handwritten drug transaction logs.

On February 24, 2006 — the day after Wolford’s arrest — Alfred Lincoln Robertson, Jr., Esq. (hereinafter “trial counsel”) was appointed to represent Wolford in this matter pursuant to the CJA, 18 U.S.C. § 3006A. In the days immediately following his appointment, but prior to meeting personally with Wolford, trial counsel (i) researched Wolford’s criminal record and background, (ii) researched developments in the law related to the case, (iii) spoke with government counsel regarding the charged conduct, and (iv) reviewed the criminal complaint and supporting affidavit. See Trial Counsel’s CJA Voucher (Doc. 104, Ex. C) (hereinafter “CJA Voucher”). Trial counsel then met with Wolford on February 28, 2006, to discuss the facts of the case and “strategy.” Id. A detention hearing was also held on February 28, 2006, at the conclusion of which Wolford was released on certain conditions, including the special condition — requested jointly by trial counsel and government counsel — that Wolford attend a Phoenix House 90-day inpatient drug treatment program. The matter was thus scheduled for a status conference on May 23, 2006, following Wolford’s anticipated release from the Phoenix House program.

While Wolford was at the Phoenix House, trial counsel continued to engage in case-related discussions with government counsel and the assigned law enforcement agents. In this regard, trial counsel held a meeting with the case agents and government counsel on March 7, 2006, to discuss the facts of the case and the charged conduct. See CJA Voucher. The record also reflects that the government extended its first written plea offer to Wolford on that date. Specifically, in a letter addressed to trial counsel dated March 7, 2006, the government proposed that Wolford plead guilty to two offenses, namely (i) one count of conspiracy to distribute controlled substances, in violation of 21 U.S.C. § 846, with a projected guidelines base offense level of 28 to 30 based on drug quantity, and (ii) one count of health care fraud, in violation of 18 U.S.C. § 1347. See Gov’t Ex. 1 to Oct. 9, 2009 Hr’g. In return for Wolford’s plea of guilty to these two charges, the government agreed in the March 7, 2006 letter that it would not charge Wolford for engaging in criminal conduct in a protected area — the elementary school located within 1,000 feet of her residence — and that it would not seek any additional adjustments or enhancements to her offense level related to “gun, role, or juveniles.” M

Trial counsel received and reviewed the government’s March 7, 2006 letter, and while he does not specifically recall discussing that particular plea offer with Wolford, he testified that it was his usual practice in 2006, as it has been throughout his entire legal practice, “to tell clients of every plea offer.” See Oct. 9, 2009 Hr’g Tr. (hereinafter “Tr.”) at 154. Trial counsel further noted that “[ejvery offer made in any type of case, I’ve always reported to a client what the basic outlines and basic terms were.” Id Trial counsel’s certified voucher includes an entry listed as “review proposed plea agreement” on March 7, 2006, but no additional entry is included around this time period reflecting that trial counsel disclosed or discussed the March 7, 2006 plea offer with Wolford. See CJA Voucher. Instead, the voucher reflects that trial counsel first contacted the Phoenix House on March 9, 2006, in an effort to ascertain the proper procedures for contacting Wolford during her participation in the inpatient drug treatment program, but that he did not speak personally with Wolford on that date. Id. Wolford, for her part, likewise does not remember “anyone” telling her about a plea offer extended by the government in March 2006. Tr. at 24.

Between mid-March and late April 2006, trial counsel did not perform any substantive work in connection with this case with the exception of engaging in several telephone discussions with government counsel and with Wolford concerning an extension of the indictment period. See CJA Voucher. In this regard, the record reflects that during Wolford’s stay at the Phoenix House, the government filed two motions, pursuant to 18 U.S.C. § 3161(h), to extend the time for filing an indictment beyond the otherwise applicable Speedy Trial Act deadline based on the fact that the parties were engaged in ongoing plea negotiations. Both motions for an extension of the indictment period were granted, the first on March 29 and the second on April 30, 2006. United States v. Wolford, 1:06cr113 (E.D.Va. Mar. 29 and Apr. 30, 2006) (Orders).

Approximately two weeks prior to her completion of the Phoenix House program, Wolford appeared, with trial counsel, at a May 23, 2006 status conference. Tr. at 24. In the course of that hearing, the government submitted yet another consent motion, pursuant to 18 U.S.C. § 3161(h), to extend the time for filing an indictment based on the parties’ ongoing plea negotiations. This third motion, like the previous motions, was granted, thereby extending the indictment period until June 29, 2006. United States v. Wolford, 1:06cr113 (E.D.Va. May 23, 2006) (Order). According to Wolford, trial counsel was “excited” at the conclusion of the May 23, 2006 status hearing and told Wolford as they were leaving the courthouse that the government “was even going to recommend 5K.” Tr. at 26. Wolford does not recall asking trial counsel on that occasion what 5K meant, but she “assumed from then on,” incorrectly of course, that “5K meant probation.” Tr. at 26.

On May 25, 2006, a “de-brief and proffer” session was held at the Phoenix House, during which Wolford and trial counsel met for approximately two to three hours with several government agents, including the lead case agent, Matthew Schneck. See CJA Voucher; Tr. at 28. At that meeting, Wolford signed an immunity agreement — a document that she described as providing that anything she said in the course of the meeting “could not be held against [her] but anything [she] lied about ... could be held against [her].” Tr. at 30-31. Among the subjects discussed at the May 25, 2006 meeting was Wolford’s possible cooperation with law enforcement authorities. In this regard, Wolford indicated that she was not willing to wear a wire into a doctor’s office, as the agents asked, but that she “would show them how” to get pills by taking an undercover law enforcement agent posing as Wolford’s “cousin” with her to the doctor’s office. Tr. at 32.

In the days following the May 25, 2006 proffer session at the Phoenix House, trial counsel spoke separately with both Wolford and government counsel about the details of the meeting and the possible scheduling of a plea hearing. See CJA Voucher. Then, on June 15, 2006, trial counsel received and reviewed a “plea form from the government.” Id. Later that day, trial counsel spoke with Wolford on the telephone regarding the government’s plea offer. Id. Shortly thereafter, on June 19, 2006, and presumably at the parties’ request, the Clerk’s Office scheduled a plea hearing in this matter for June 20, 2006. Wolford, who was then on conditions of release, was directed to appear at the courthouse on June 20 for, as she put it, “a plea- — -plea negotiation — plea agreement.” Tr. at 33.

Wolford arrived at the courthouse on June 20, 2006, accompanied by her father and trial counsel, but the plea hearing did not go forward as scheduled. Instead, the government filed, and the trial judge granted, a fourth motion for an extension of the indictment period. United States v. Wolford, 1:06cr113 (E.D.Va. June 20, 2006) (Order). Also on that date, and at trial counsel’s request, the parties met for approximately two to three hours in a conference room outside the trial judge’s courtroom to review the terms of the government’s plea offer. Tr. at 230. Present at this meeting were (i) Wolford, (ii) Wolford’s father, (iii) trial counsel, (iv) government counsel, (v) Agent Schneck, the lead case agent, (vi) Detective Jimmy Horton from the Manassas City Police Department, and (vii) possibly another government agent. Tr. at 35, 158.

According to Agent Schneck, “[t]he case in its entirety was discussed” in the course of the lengthy June 20 meeting. Tr. at 230. During that meeting, government counsel also reviewed with Wolford, in detail, the terms of the government’s plea offer, as well as the proposed plea doeuments. And, with the exception of the health care fraud offense, which had been eliminated from the government’s plea offer at trial counsel’s request, the essential terms of the government’s June 20, 2006 plea offer were precisely the same as those that had been offered previously in March 2006. In other words, Wolford was offered the opportunity to plead guilty to a single charge of conspiracy, with a recommended base offense level of 28 to 30 based on drug quantity, and without any additional charges or requested enhancements related to Wolford’s role in the offense, the firearm found in her residence, or the fact that the criminal activity occurred in a protected area.

In addition to discussing the specific terms of the government’s plea offer and the proposed plea documents, government counsel, in the course of the June 20, 2006 meeting, also reviewed the following with Wolford: (i) the evidence and testimony the government would present against her were the matter to proceed to trial, including evidence of multiple drug transactions between Wolford and a confidential informant, some of which were captured on audio tape, Tr. at 230; (ii) the statutory maximum penalties for the applicable offenses, Tr. at 159; (iii) the possible sentence Wolford might receive were she to be convicted at trial, Tr. at 230; (iv) the possible sentence Wolford might receive were she to plead guilty and cooperate with the government pursuant to the proposed plea agreement, Tr. at 230; (v) the possibility of the government filing a motion to reduce Wolford’s sentence based on her cooperation with law enforcement authorities, pursuant to U.S.S.G. § 5K1.1 or Rule 35, Fed. R. Crim. P., Tr. at 159; (vi) the quantity of pills and drug offense level for which the government sought to hold Wolford responsible in the proposed plea agreement, Tr. at 159-60; and (vii) the sentencing guidelines, Tr. at 234. According to Agent Schneck, Wolford appeared to understand all of the terms set forth in the proposed plea documents reviewed with her during the June 20, 2006 meeting. Tr. at 232.

With respect to the possible sentence, government counsel advised Wolford in the course of the June 20, 2006 meeting that she could receive “approximately 20 years” of imprisonment were she to be convicted following a jury trial, but that “if she pled with cooperation, she’s looking at approximately two to three years,” assuming the government’s filing and the trial judge’s granting of a motion for a reduction in her sentence, pursuant to U.S.S.G. § 5K1.1 or Rule 35, Fed. R. Crim. P. Tr. at 85, 230-31. Agent Schneck does not recall any group discussion during the course of the June 20, 2006 meeting concerning Wolford’s criminal record or her likely criminal history calculation under the sentencing guidelines. Tr. at 233. Yet, trial counsel recalls showing Wolford the senteneing table set forth in the guidelines’ manual and telling her that he “was pretty-confident that her criminal history category would be a one.” Tr. at 165-66. And although trial counsel does not specifically recall advising Wolford what her likely offense level would be were she to accept the government’s plea offer, he correctly notes that the proposed plea documents, which were reviewed in full with Wolford in the course of the June 20, 2006 meeting, included information concerning the applicable offense level. Tr. at 166. Indeed, the proposed statement of facts expressly provided that Wolford, were she to accept the government’s plea offer, would be held accountable for the distribution of “Oxy and other pain pills ... in an amount convertible to level 30 of the USSG.” Gov’t Ex. 4 to Oct. 9, 2009 Hr’g.

The record is undisputed that Agent Schneck and government counsel provided much of the verbal explanation to Wolford during the course of the June 20, 2006 meeting. Nonetheless, it is equally clear that trial counsel also reviewed the proposed plea documents with Wolford on that occasion. Tr. at 40, 164-65, 195. Indeed, trial counsel specifically recalls reviewing the terms of the plea documents with Wolford in private, while the government representatives waited outside the conference room. Tr. at 195. In fact, trial counsel estimates that he spent approximately 30 to 40 percent of the two to three hour meeting with Wolford in private, while the remaining time was spent with the entire group. Tr. at 196.

In the end, Wolford did not agree to the terms of the government’s plea offer on June 20, 2006. Specifically, she admits that she read and reviewed the proposed plea documents during the course of the June 20, 2006 meeting, but testified that she was “not comfortable” signing the papers and “wasn’t ready” to enter a guilty plea on that date. Tr. at 36, 41. The record reflects that Wolford had two primary concerns at that time. First, she was concerned about the quantity of drugs for which the government sought to hold her accountable in the proposed plea agreement. As to this issue, Wolford testified that she did not believe that she had distributed “thousands and thousands of pills,” as indicated in the proposed statement of facts, and thus, that she could not “put [her] hand on a bible and swear that [she] did something that [she] didn’t do.” Tr. at 39. Yet significantly, the record is clear that Wolford did not ever dispute that she had distributed some quantity of controlled substances in this instance; instead, she merely contested the specific quantity of drugs for which she would be held responsible were she to accept the government’s plea offer. Tr. at 40.

Wolford’s second concern with accepting the government’s plea offer on June 20, 2006, related to her desire to avoid any period of incarceration. Indeed, she testified that a “major motivation” for her rejecting the government’s June 20, 2006 plea offer was that she wanted the government to agree that she would not be required to serve any time in jail if she pled guilty. Tr. at 87-88. Trial counsel likewise testified that Wolford did not want to serve any jail time and that her “goal was always to obtain a plea for probation only if she pled at all.” Tr. at 160. Thus, when trial counsel asked Wolford in June 2006 if she would be willing to accept a plea agreement that did not guarantee her probation, she remained “very insistent that she wanted no jail time” and “did not want to consider going to jail at all.” Tr. at 185-86. Consistent with this, Agent Schneck testified that Wolford “was not satisfied” with the plea offer extended by the government on June 20, 2006, because she wanted to serve “zero” confinement. Tr. at 231.

By letter dated June 25, 2006, the government reiterated its offer to allow Wolford to plead guilty in accordance with the terms that had been reviewed with her in the course of the June 20, 2006 meeting. Gov’t Ex. 2 to Oct. 9, 2009 Hr’g. Trial counsel received, reviewed and promptly disclosed the government’s June 25, 2006 written plea offer to Wolford. See CJA Voucher. Trial counsel also reviewed with Wolford the terms set forth in the government’s June 25, 2006 plea offer, including specifically (i) the projected offense level, (ii) the fact that the government still wanted Wolford to plead guilty to a conspiracy charge, (iii) the government’s agreement not to pursue any additional charges arising out of the fact that the offense occurred in a protected area, and (iv) the government’s agreement not to pursue “the gun adjustment.” Tr. at 155-56.

By its terms, the government’s June 25, 2006 written plea offer provided that it would “expire on Monday, July 10, 2006,” in the event Wolford did not expressly accept the offer by that date. Gov’t Ex. 2 to Oct. 9.2009 Hr’g. Trial counsel spoke with government counsel concerning the outstanding plea offer on July 10; trial counsel also spoke with Wolford for nearly an hour on that date regarding the “plea and strategy.” See CJA Voucher. Yet, the record does not reflect that trial counsel ever advised Wolford that the government’s June 25, 2006 written plea offer included an express deadline of July 10, 2006.

Approximately two weeks later, on July 25, 2006, trial counsel had separate telephone conversations with government counsel and Wolford concerning the government’s filing of a fifth motion to extend the indictment period. Such a motion was then filed by the government on that date and subsequently granted by the trial judge, thereby extending the period in which the government was required to file an indictment in this matter until August 10, 2006. United States v. Wolford, 1:06cr113 (E.D.Va. Aug. 3, 2006) (Order). Prior to this deadline, on August 8, 2006, trial counsel spoke on the telephone with government counsel regarding another “proffer.” See CJA Voucher. On the same day, trial counsel spoke with Wolford on two occasions — once for nearly an hour — -regarding this “proffer.” Id. Trial counsel also directed Wolford to appear at the courthouse for a meeting with the government and trial counsel for the “proffer” session that had been discussed on August 8, 2006, but ultimately the session was not held owing to the government’s unavailability. Tr. at 45.

On August 10, 2006 — the last day of the fifth authorized extension period — a federal grand jury returned the initial indictment in this matter charging Wolford and McCauley with one count of conspiracy to distribute oxycodone, methadone and cocaine, in violation of 21 U.S.C. § 846 (Count One). Wolford was also charged in the initial indictment with the following two substantive drug counts: (i) distribution of oxycodone, in violation of 21 U.S.C. § 841(a) (Count Two) and (ii) distribution of oxycodone within 1,000 feet of an elementary school, in violation of 21 U.S.C. § 860(a) (Count Three).

On August 11, 2006, the day after the indictment was returned, Wolford appeared with trial counsel for an arraignment hearing before the trial judge. In the course of the hearing, Wolford, by trial counsel, entered a plea of not guilty, waived formal reading of the indictment and requested a trial by jury. A jury trial was thus scheduled to commence on November 28, 2006. Immediately following the arraignment, Wolford and trial counsel spoke briefly with government counsel and Agent Schneck in the hallway outside the courtroom. During that conversation, Wolford again expressed concern about the quantity of drugs for which she would be held accountable were she to accept the government’s plea offer, stating words to the effect of, “We’re talking less than a handful of pills.” Tr. at 46. Agent Schneck, in response, reviewed with Wolford how the government had calculated its recommended drug quantity for sentencing-related purposes, namely by estimating the total amount of controlled substances obtained and distributed by Wolford and her co-conspirators during the course of the conspiracy, regardless of whether some of those controlled substances were obtained for personal use by Wolford or other co-conspirators. Tr. at 232-33. Wolford correctly understood Agent Schneck’s explanation to mean that “if you distribute one pill out of a bottle that meant the whole bottle” could be counted for drug calculation purposes. Tr. at 46. In other words, Wolford understood “that if [she] got a prescription ... from the pharmacy and distributed one pill, that it’s part of the conspiracy that [she] distributed all of them.... ” Tr. at 65.

At the conclusion of the August 11, 2006 discussion outside the courtroom, government counsel suggested that the parties meet again in two weeks, presumably for further plea discussions. Tr. at 47. According to Wolford, she responded “Yes” to government counsel’s suggestion in this regard, but trial counsel said “No,” advising Wolford that he would “talk about it [with her] later.” Id. Then, when Wolford later asked trial counsel to set up another plea meeting with the government, he responded by telling her that the government was “never going to agree to anything you want.” Id. In this regard, trial counsel advised Wolford that the government was “never going to offer [her] probation” in exchange for her guilty plea, and that the closest she might come to receiving a sentence of probation was “if she were to plead [guilty] and work a deal and do all the things [the government] wanted her to do in cooperation.” Tr. at 225. Similarly, trial counsel told Wolford “that the only chance she really [had] to get a Rule 35 or a 5K” was if she pled guilty. Tr. at 226. Finally, trial counsel advised Wolford that were she to plead guilty, she would likely receive a two-level reduction to her offense level, pursuant to U.S.S.G. § 3El.l(a), for acceptance of responsibility; trial counsel does not specifically recall advising Wolford about the third level of credit for acceptance of responsibility permissible on the government’s motion under U.S.S.G. § 3E1.1(b). Tr. at 167-68.

On August 30, 2006, trial counsel met with Wolford for approximately one hour to discuss “trial strategy.” See CJA Voucher. The following day, trial counsel received and reviewed another government plea offer and accompanying proposed plea documents. These documents included a 17-page proposed plea agreement signed by the government on August 31, 2006, together with a proposed criminal information and statement of facts, both signed by the government without a date, as well as an unsigned and undated waiver of indictment. Govt. Ex. 4 to Oct. 9.2009 Hr’g.

Unlike the June 25, 2006 written plea offer, the government’s August 31, 2006 plea offer did not appear to have an express deadline. Moreover, the terms of this offer were essentially the same as those that previously had been extended to Wolford, both in the June 20, 2006 group plea meeting and again in the government’s June 25, 2006 written plea offer. Thus, the government’s August 31, 2006 plea offer contemplated Wolford entering a plea of guilty to a one-count criminal information charging her with conspiracy to distribute oxycodone, in violation of 21 U.S.C. § 846. Also consistent with the government’s June 2006 offers, the August 31, 2006 proposed plea documents sought to hold Wolford accountable for the distribution of “Oxy and other pain pills ... in an amount convertible to level 30 of the U.S.S.G. § ,” with no additional charges or enhancements related to (i) Wolford’s role in the offense, (ii) the firearm found at her residence, or (iii) the fact that the criminal activity occurred in a protected location. Gov’t Ex. 4 to Oct. 9, 2009 Hr’g.

The record reflects that trial counsel promptly disclosed the government’s August 31, 2006 plea offer to Wolford. Indeed, counsel’s certified voucher confirms that he spoke with Wolford concerning the plea offer for over thirty minutes on August 31, 2006. See CJA Voucher. Notably, this conversation is the last plea-related entry included in trial counsel’s voucher. Trial counsel nonetheless testified that he continued to speak generally with Wolford “about taking the plea almost all the way up to the trial .date.” Tr. at 162. In this regard, trial counsel recalls having “many separate discussions” with Wolford throughout the plea negotiation process. Tr. at 181. For example, he “remember[s] recommending specifically that [Wolford] take the plea,” telling her that “[y]ou’re looking at a lot of time if you don’t take the plea.” Tr. at 213. He also advised Wolford that “[she] should be taking the plea” given the fact that the government had “a lot of evidence against [her].” Tr. at 214. In this regard, trial counsel advised Wolford on more than one occasion that “it [w]as going to be a very difficult trial” and “that it would be a very difficult case to win.” Tr. at 206, 211. Trial counsel also discussed with Wolford some of the likely consequences to her if she did not accept the government’s plea offer, including specifically (i) the possibility of the government filing a superseding indictment charging her “with many more counts than what the plea had in it,” including “the school charge,” and (ii) the fact that she would be “looking at a significant amount of jail time if she was convicted” at trial. Tr. at 181-82, 188.

Throughout the month of September 2006, trial counsel engaged in several telephone calls with government counsel and with Wolford regarding the status of the case and various discovery and trial-related matters. See CJA Voucher. During this period, trial counsel also received and reviewed the government’s proposed discovery order. Id. At the end of that month, on September 26, 2006, trial counsel met with Wolford for over an hour to prepare for trial and to discuss “defenses.” Id.

On October 5, 2006, a federal grand jury returned a ten-count superseding indictment against Wolford and McCauley, adding several new substantive distribution charges against Wolford, as well as new allegations concerning several additional types of controlled substances. Specifically, in Count One, Wolford was charged with conspiring with McCauley and others to distribute oxycodone, hydromorphone, methadone hydrochloride, dextroamphetamine, morphine and cocaine within 1,000 feet of a school, in violation of 21 U.S.C. §§ 841(a), 846 and 860. In addition to the conspiracy charge, Wolford was also charged with (i) eight substantive counts of distributing oxycodone and other controlled substances, in violation of 21 U.S.C. § 841(a) and 18 U.S.C. § 2 (Counts Two through Nine), and (ii) one count of distributing oxycodone and other controlled substances within 1,000 feet of a school, in violation of 21 U.S.C. § 860(a) (Count Ten).

Arraignment on the superseding indictment was held on October 12, 2006, in the course of which the trial judge directed that the jury trial would commence, as previously scheduled, on November 28, 2006. Following arraignment, government counsel met with Wolford and trial counsel outside the courtroom. According to Wolford, government counsel was visibly upset during the meeting and at one point declared, “And now we’re going to trial.” Tr. at 51. Consistent with Wolford’s recollection, trial counsel testified that around the time of the superseding indictment, government counsel told him and Wolford, “That’s it. We’re going to trial.” Tr. at 204.

In the months preceding the scheduled jury trial, trial counsel devoted a substantial amount of time to trial preparation, both on his own and together with Wolford. Trial counsel’s certified voucher alone includes entries for more than (i) 70 hours in pretrial interviews and conferences, (ii) 40 hours obtaining and reviewing discovery and other documents, (iii) 9 hours performing legal research and writing, and (iv) 7 hours performing investigative and other work. See CJA Voucher. Trial counsel also participated in numerous telephone and in-person conferences with Wolford in the months preceding trial, including conferences related specifically to “trial strategy,” “trial prep,” “elements of statute,” “case law,” “expected [trial] process,” “defenses,” “possible testimony,” and “stipulations.” Id

Wolford likewise recalls having at least two trial preparation meetings with trial counsel, including (i) a meeting at trial counsel’s office during which she reviewed all of the evidence that had been provided by the government in its open-file discovery exchange, including various documents and law enforcement reports, as well as audio tapes and transcripts of the drug transactions that had been recorded by the confidential informant, and (ii) a meeting at her parents’ home during which trial counsel spoke with her and several of her family members about the upcoming trial. Tr. at 52-54; 89-90.

Wolford also acknowledged that she met with trial counsel “approximately three times, if not more,” to discuss “[her] defense” prior to trial. Tr. at 72. Based on these discussions with trial counsel, Wolford believed that three defenses would be raised on her behalf at trial, namely (i) her alleged intoxication during the charged conspiracy, (ii) entrapment by an agent of the government, and (iii) the so-called “household” or “family member” defense. Tr. at 58. Wolford testified that she believed her “primary defense was going to be intoxication and that [she] would be showing who [she] was before, during and after” the charged conspiracy. Tr. at 55. But more significantly, Wolford testified that trial counsel “told [her] about the household instruction,” specifically advising her “that if ... the people lived in the house that it was okay to give them pills as long as they were family members.” Tr. at 60. Thus, Wolford further states in her sworn affidavit that she “believed it was legal to distribute prescription drugs to family and household members but not for money,” and that trial counsel “never, at any point during the course of his representation, told [her] otherwise.” Pet. Aff. ¶ 6.

Trial counsel, for his part, testified that he advised Wolford that “many of her defenses were what [he would] call imperfect,” meaning “that they meet some elements of what the classic defense would be but other elements it didn’t,” and that because of this, the “defense[s] didn’t make it and would not work.” Tr. at 214. For example, trial counsel “talked [with Wolford] about imperfect entrapment,” including specifically “the behavior of some of the Government’s witnesses ... and different things that Melanie [Burgess, the government’s confidential informant,] had done in this case.” Tr. at 215. Trial counsel also discussed with Wolford what he referred to as the “family member defense.” In this regard, although trial counsel does not recall whether he advised Wolford that the “family member defense” was “completely viable or not,” he did “put a lot of faith in it ... personally,” and communicated his personal belief in this purported defense to Wolford during the pretrial proceedings. Tr. at 215.

In addition to trial counsel’s advice concerning possible defenses to the charged conduct, trial counsel also advised Wolford about another possible “trial strategy” that could be pursued concerning the drug quantity for which she might eventually be held accountable were she to be convicted at trial. Tr. at 169. As to this issue, it was trial counsel’s view throughout these proceedings that Wolford should not be held criminally responsible for purposes of a drug conspiracy or distribution charge for any quantity of controlled substances or pills that she personally ingested. Id. Trial counsel remained steadfast in this view even up to the time of sentencing, despite the fact that the contrary view— advocated by the government throughout the plea negotiation proceedings — was supported by Fourth Circuit precedent. Trial counsel also recalls discussing his view in this regard with Wolford prior to trial, advising her “about how [he] thought [her personal drug use] should affect what her guidelines would be in sentencing and using that as a possible trial strategy.” Tr. at 169-70. In this regard, trial counsel testified that he hoped to “eat away” at the applicable drug quantity at trial by “showing that [Wolford] wasn’t responsible for this ... offense in as large amount as the Government thought she was.” Tr. at 216. In other words, trial counsel believed that Wolford’s personal use of many of the prescription drugs involved in the charged conspiracy might, as he put it, “ameliorate the consequence in the long run to Ms. Wolford.” Tr. at 170.

Significantly, trial counsel acknowledged in the course of the October 9, 2009 evidentiary hearing that “the more [he] look[s] at it,” “[he] never really thought [he] could beat the conspiracy” charge at trial. Tr. at 216. Yet, the record does not reflect that trial counsel ever advised Wolford of his view in this regard during the pretrial and plea negotiation proceedings. Nor does the record reflect that trial counsel ever advised Wolford about the impact and significance of relevant conduct in determining a defendant’s sentencing guidelines range. For example, trial counsel did not advise Wolford that were she to be convicted of the conspiracy charge at trial, “it didn’t matter how many other charges she’s acquitted of she was going to get hit for the whole [drug] weight.” Tr. at 215-16. Similarly, the record does not reflect that trial counsel ever advised Wolford that a conviction on the conspiracy charge alone would render her accountable for all of the “reasonably foreseeable” controlled substances that she and her eo-conspirators distributed and possessed with the intent to distribute during the course of the conspiracy. See U.S.S.G. § 1B1.3 (providing that “in the case of a jointly undertaken criminal activity,” a defendant’s base offense level shall be determined on the basis of the defendant’s own acts as well as “all reasonably foreseeable acts and omissions of others in furtherance of the jointly undertaken criminal activity”); United States v. Lamarr, 75 F.3d 964, 972 (4th Cir.1996) (recognizing that “[a] defendant’s Base Offense Level under the Guidelines is determined by the amount of drugs reasonably foreseeable to him within the scope of the unlawful agreement”). Nor does it appear in this record that trial counsel advised Wolford that the applicable drug quantity for sentencing-related purposes would ultimately be determined by the trial judge using only a preponderance of the evidence standard, provided the resulting sentence was still within the allowable statutory range of imprisonment. See United States v. Brooks, 524 F.3d 549, 560 n. 20 (4th Cir.2008) (noting that “[although a sentencing court is free to calculate the advisory Guidelines range using facts that it finds by a preponderance of the evidence, including individualized drug quantities, it must do so within the confines of the applicable statutory range” given the Supreme Court’s decisions in Apprendi v. New Jersey, 530 U.S. 466, 120 S.Ct. 2348, 147 L.Ed.2d 435 (2000) and United States v. Booker, 543 U.S. 220, 125 S.Ct. 738, 160 L.Ed.2d 621 (2005)). Indeed, Wolford states in her sworn affidavit that trial counsel “never explained to [her] that as long as [she] was found guilty of one charge, the court could sentence [her] based on conduct [she] was acquitted of or any other conduct not alleged but proven at [her] sentencing by a preponderance of the evidence.” Pet. Aff. ¶ 11.

In sum, then, the record reflects the following essential facts concerning trial counsel’s advice to Wolford during the plea negotiation and pretrial proceedings in this matter:

• Trial counsel properly and promptly disclosed to Wolford the government’s June 2006 and August 2006 plea offers.

• Wolford (i) read the proposed plea documents provided by the government in June 2006, (ii) reviewed and discussed those documents, both with trial counsel alone, and with trial counsel and government representatives in a group setting, and (iii) understood the essential terms of the plea offer extended by the government in June 2006, and then again in August 2006. Specifically, Wolford understood that these plea offers provided her with the opportunity to plead guilty to a single charge of conspiracy, with a recommended base offense level of 28 to 30 based on drug quantity, and without any additional charges or recommended enhancements related to her role in the offense, the firearm found in her residence, or the fact that the criminal activity occurred in a protected area.

• Wolford did not accept the government’s June 2006 or August 2006 plea offers because (i) she did not agree with the specific quantity of drugs for which the government sought to hold her responsible in the proposed plea documents, and (ii) she did not want to serve any jail time. Wolford nonetheless wanted to reach a plea agreement with the government in this case, as she did not dispute that she had distributed some quantity of controlled substances during the relevant period.

• Trial counsel appropriately advised Wolford that the government was not going to agree to recommend a sentence of probation with no jail time, as Wolford wanted, and that the closest she might come to a probationary sentence would be to accept the government’s plea offer and cooperate with the government. Trial counsel also advised Wolford that she should accept the government’s plea offer in light of the substantial evidence against her and the risk of additional charges being filed and pursued against her at trial, including the school charge. Wolford was further advised, both by trial counsel and government counsel, that she would be subject to a much more severe sentence were she to be convicted at trial rather than accept the government’s plea offer.

• Throughout the pretrial proceedings, trial counsel advised Wolford that three defenses would be pursued on her behalf were she to proceed to trial, namely: (i) intoxication, (ii) entrapment, and (iii) the “family member defense.” The record does not reflect whether trial counsel ever specifically advised Wolford that these defenses were “completely viable.” Tr. at 215. Yet, trial counsel admits that he communicated to Wolford his strong personal belief in the so-called “family member defense” prior to trial. Tr. at 215. Given this, Wolford continued to decline the government’s plea offers and proceeded to trial believing incorrectly that “it was legal to distribute prescription drugs to family and household members but not for money” and “that in order to be guilty, the government had to prove that [she] sold people drugs for profit.” Pet. Aff. ¶ 6. Trial counsel also incorrectly advised Wolford that her personal drug use might be a “possible trial strategy,” as he did not agree with the government that Wolford should be held criminally accountable for drugs that she personally ingested during the alleged conspiracy-

• Although trial counsel was clearly well-meaning throughout the plea negotiation process, the record reflects that he never advised Wolford about the impact and significance of relevant conduct in determining a defendant’s sentencing guidelines range. For example, trial counsel did not advise Wolford that a conviction at trial on the conspiracy charge alone would render her accountable for all of the “reasonably foreseeable” controlled substances that she and her co-conspirators distributed and possessed with the intent to distribute during the entire course of the conspiracy. U.S.S.G. § 1B1.3. Similarly, trial counsel never advised Wolford “that as long as [she] was found guilty of one charge, the court could sentence [her] based on conduct [she] was acquitted of or any other conduct not alleged but proven at [her] sentencing by a preponderance of the evidence,” provided that the sentence was within the applicable statutory range of imprisonment. Pet. Aff. ¶ 11.

Just days before the scheduled trial, Wolford wrote a letter to the trial judge requesting a continuance to provide her and trial counsel additional time to prepare for trial. Tr. at 56. In response to Wolford’s letter, the trial judge held a status conference on November 27, 2006, in the course of which Wolford reiterated her request for a continuance. Trial counsel supported Wolford’s request in this regard, indicating that he had “been busy with a lot of state cases” and would benefit from additional time to prepare for trial; trial counsel represented that he “could be ready in a week.” Tr. at 57. In the circumstances, the trial judge granted Wolford’s motion and continued the trial for one week, to December 4, 2006. On that day, Wolford orally requested a second continuance of the trial, this time requesting that trial counsel be removed from the case and that she be given additional time to retain new counsel to represent her at trial. Tr. at 57. The trial judge denied Wolford’s oral request for a second continuance, but nonetheless provided her the option of representing herself at trial, with trial counsel to serve as standby counsel. Alternatively, Wolford was granted leave to retain new counsel to represent her at trial, provided that such counsel was willing and able to commence trial the following day. In the end, the jury trial was continued one additional day.

Trial began on December 5, 2006, with trial counsel continuing to serve on Wolford’s behalf. In the course of the trial, the government presented extensive evidence and testimony from more than twenty witnesses establishing overwhelmingly that from 2001 to 2006, Wolford conspired with McCauley and others to distribute large quantities of various controlled substances, including oxycodone, out of Wolford’s Manassas residence, which was located within 1,000 feet of an elementary school. The trial evidence established that most of these controlled substances were obtained by Wolford and McCauley through written prescriptions from known physicians, while additional quantities were purchased from other suppliers or obtained from other users or suppliers through trade.

Among the government’s testifying witnesses at trial were (i) McCauley, who testified at length about the nature and extent of the charged conspiracy, (ii) numerous individuals who either sold, purchased or traded controlled substances with Wolford and McCauley during the course of the conspiracy, and (iii) the confidential informant who purchased controlled substances from Wolford on multipie occasions and recorded several of these transactions on audio tape. Wolford also testified on her own behalf and, after initially denying the charged conduct, eventually admitted that she distributed controlled substances during the relevant time period, both to family members and to other individuals who were neither household nor family members.

Not surprisingly, on December 14, 2006, following approximately six days of testimony and deliberations, the jury trial culminated in a guilty verdict on the conspiracy charged in Count One of the superseding indictment. Wolford was also convicted of the substantive drug counts charged in Counts Three and Four, but was acquitted as to the remaining counts. Based on the trial record, and with the inclusion of additional uncharged and acquitted relevant conduct found by the trial judge to have been established by a preponderance of the evidence, Wolford was held accountable for the equivalent of 21,626.76 kilograms of marijuana in the Presentence Investigation Report (PSIR), placing her in a base offense level of 36. This base offense level was then increased by a total of six levels, comprised of (i) a two-level enhancement pursuant to U.S.S.G. § 2D1.2(a)(1) because the offenses occurred near a protected location, (ii) a two-level enhancement pursuant to U.S.S.G. § 3Bl.l(c) because Wolford was “an organizer, leader, manager or supervisor” in the charged criminal activity, and (iii) a two-level obstruction of justice enhancement pursuant to U.S.S.G. § 3C1.1 based on Wolford’s untruthful testimony at trial. This total offense level of 42, combined with Wolford’s calculated criminal history category of II, resulted in a guidelines range of imprisonment of 360 months to life. Ultimately, on March 19, 2007, after adopting the factual findings and guidelines calculations set forth in the PSIR, the trial judge sentenced Wolford to concurrent terms of imprisonment of 108 months as to each of the three counts of conviction, a very significant downward variance (more then 250 months) from the bottom of the applicable guidelines range of imprisonment.

Following sentencing, Wolford retained new counsel, who then assisted her in filing a timely direct appeal to the Court of Appeals for the Fourth Circuit. In the appeal, Wolford raised only two arguments, namely (i) that the trial judge erred by failing to order a competency hearing in this case, and (ii) that trial counsel was ineffective in several respects. On April 2, 2008, the Fourth Circuit affirmed Wolford’s convictions and sentence by unpublished per curiam opinion. See United States v. Wolford, 271 Fed.Appx. 372 (4th Cir.2008). Specifically, the Fourth Circuit concluded, first, that the trial judge had not abused his discretion in failing to order a competency hearing and second, that Wolford had “failed to meet the demanding burden of showing ineffective assistance of trial counsel on direct appeal.” Id. at 373. In so holding, the Fourth Circuit specifically noted that “to allow for adequate development of the record, claims of ineffective assistance generally should be brought in a 28 U.S.C. § 2255 (2000) motion.” Id. (citing United States v. Hoyle, 33 F.3d 415, 418 (4th Cir.1994)).

On June 30, 2009, Wolford, by newly retained counsel — different from the retained counsel who filed the direct appeal on her behalf — filed a timely motion to vacate, set aside or correct sentence, pursuant to 28 U.S.C. § 2255. In the instant motion, Wolford raises five claims: (i) that the trial judge abused his discretion in denying Wolford’s second motion for a continuance of the trial, (ii) that trial counsel was ineffective during the plea negotiation and pretrial proceedings, (iii) that trial counsel was ineffective in preparing for the jury trial, (iv) that trial counsel was ineffective in failing to object to an alleged prejudicial comment made by the trial judge in the course of the trial, and finally (v) that trial counsel was ineffective in the course of the sentencing proceedings. Wolford also contends that appellate counsel was ineffective in failing to raise several of these arguments on direct appeal.

An evidentiary hearing concerning Wolford’s § 2255 allegations was held on October 9, 2009, in the course of which the parties presented evidence and testimony from five witnesses, namely (i) Wolford, (ii) Wolford’s brother, (iii) appellate counsel, (iv) trial counsel, and (v) Agent Schneck. Wolford’s § 2255 claims are thus ripe for disposition and are addressed here.

II.

Wolford’s claims are governed by well-settled legal principles. In this regard, it is clear that collateral review under § 2255 is limited. Specifically, to be entitled to relief under § 2255, a prisoner must demonstrate either a lack of jurisdiction by the convicting court, a constitutional error, or a legal error so grave as to constitute “ ‘a fundamental defect which inherently results in a complete miscarriage of justice.’” United States v. Addonizio, 442 U.S. 178, 185, 99 S.Ct. 2235, 60 L.Ed.2d 805 (1979) (quoting Hill v. United States, 368 U.S. 424, 428, 82 S.Ct. 468, 7 L.Ed.2d 417 (1962)). In this case, the majority of Wolford’s § 2255 claims are constitutional in nature, as they involve allegations of ineffective assistance of counsel in violation of the Sixth Amendment.

It is well-established that a two-prong analysis applies to an ineffective assistance of counsel claim. See Strickland v. Washington, 466 U.S. 668, 688-89, 104 S.Ct. 2052, 80 L.Ed.2d 674(1984). Specifically, to prevail on such a claim, a petitioner must show, first, that counsel’s performance “fell below an objective standard of reasonableness.” Id. at 688, 104 S.Ct. 2052. Judicial review of counsel’s performance in this context is “highly deferential.” Id. at 689, 104 S.Ct. 2052. Indeed, to establish that counsel’s performance was objectively unreasonable, a petitioner must overcome the strong presumption that counsel rendered “adequate assistance and made all significant decisions in the exercise of reasonable judgment.” Id. at 690, 104 S.Ct. 2052.

If a petitioner is able to demonstrate that counsel’s performance was objectively unreasonable, Strickland next requires the petitioner to establish that “the deficient performance prejudiced the defense.” Id. at 688, 104 S.Ct. 2052. Specifically, in step two of the Strickland analysis, a petitioner must demonstrate “that there is a reasonable probability that, but for counsel’s unprofessional errors, the result of the proceeding would have been different.” Id. at 694, 104 S.Ct. 2052. A proper prejudice analysis also requires consideration of whether “the result of the proceeding was fundamentally unfair or unreliable.” Lockhart v. Fretwell, 506 U.S. 364, 369, 113 S.Ct. 838, 122 L.Ed.2d 180 (1993). Thus, counsel may be deemed constitutionally ineffective only if his or her “conduct so undermined the proper functioning of the adversarial process that the trial cannot be relied on as having produced a just result.” Strickland, 466 U.S. at 686, 104 S.Ct. 2052.

Significantly, when a federal prisoner raises a claim that could have been, but was not, pursued on direct appeal, “the movant must show cause and actual prejudice resulting from the errors of which he complains or he must demonstrate that a miscarriage of justice would result from the refusal of the court to entertain the collateral attack.” United States v. Mikalajunas, 186 F.3d 490, 492-93 (4th Cir.1999) (citations omitted). In this regard, “[t]he existence of cause for a procedural default must turn on something external to the defense, such as the novelty of the claim or a denial of effective assistance of counsel.” Id. at 493 (citation omitted). Alternatively, “in order to demonstrate that a miscarriage of justice would result from the refusal of the court to entertain the collateral attack, a movant must show actual innocence by clear and convincing evidence.” M

It remains to apply these guiding principles to Wolford’s specific § 2255 claims.

A.

Wolford’s first § 2255 claim is that the trial judge abused his discretion in denying her second motion for a continuance of the jury trial. Because this issue could have been, but was not raised on direct appeal, Wolford “must show cause [for the procedural default] and actual prejudice resulting from the errors of which [s]he complains .... ” Mikalajunas, 186 F.3d at 492-93.

Here, Wolford argues that appellate counsel was constitutionally ineffective in failing to raise the continuance issue on direct appeal. This alleged ineffective assistance, she contends, satisfies the requisite cause for the procedural default. Simply put, Wolford’s claim in this regard must be rejected, as she is unable to establish that appellate counsel was ineffective in this respect. This is so in light of the credible and undisputed testimony presented by appellate counsel in the course of the evidentiary hearing. To be sure, appellate counsel testified that he raised two issues on Wolford’s behalf on direct appeal, one related to trial counsel’s failure to request — and the trial judge’s failure to hold sua sponte — a competency hearing prior to Wolford’s trial, and the second pertaining to trial counsel’s alleged ineffective assistance in the course of the proceedings. Tr. at 116-20. Although appellate counsel knew that Wolford’s second motion to continue the trial had been denied by the trial judge, he opted not to raise the continuance issue on appeal for a number of reasons, namely (i) the second continuance motion was made on the eve of trial and, in his experience, “courts do not look favorably on motions for continuances on the eve of trial,” (ii) the motion was essentially granted in part, as the trial was continued an additional day, having already been continued a full week on Wolford’s first motion to continue, and (iii) he did not believe that objecting to the denial of Wolford’s second motion to continue would be “beneficial to the appeal.” Tr. at 121. In fact, appellate counsel further testified that he did not believe Wolford had any particularly strong arguments on direct appeal and that had he been appointed, rather than retained, he would have considered filing an Anders brief stating the same. Tr. at 126.

Given appellate counsel’s credible and undisputed testimony, Wolford is unable to overcome the strong presumption that appellate counsel rendered “adequate assistance and made all significant decisions in the exercise of reasonable judgment,” including specifically his decision not to appeal the trial judge’s denial of Wolford’s second motion for a continuance. Strickland, 466 U.S. at 690, 104 S.Ct. 2052; see also Jones v. Barnes, 463 U.S. 745, 754, 103 S.Ct. 3308, 77 L.Ed.2d 987 (1983) (recognizing that appellate counsel is not required to raise every non-trivial issue on appeal). Wolford is also unable to establish the requisite prejudice arising out of appellate counsel’s failure to raise the continuance issue on direct appeal, as such an argument would surely have been rejected by the Fourth Circuit for the reasons discussed infra. Thus, because Wolford is unable to establish that appellate counsel was ineffective in failing to raise the continuance issue on direct appeal, her § 2255 claim that the trial judge erred in denying her second motion for a continuance must be denied as procedurally defaulted.

Even absent the procedural default, Wolford’s § 2255 claim on the continuance issue would nonetheless fail on the merits. In this regard, it is clear that the denial of a motion for a continuance is reviewed for an abuse of discretion. See United States v. Hedgepeth, 418 F.3d 411, 419 (4th Cir.2005) (noting that “a trial court’s denial of a continuance is ... reviewed for abuse of discretion”). Here, the record reflects that the trial judge viewed Wolford’s second motion for a continuance of the trial — made by Wolford orally on the morning of the already-continued trial — as a delay tactic. Indeed, the trial judge specifically noted on the record that he believed Wolford was “stalling” and that she had “play[ed] games with the Court.” Tr. of 12/3/06 Hrg. at 4, 9, 11. The trial judge therefore denied Wolford’s request for an additional continuance of the trial, but nonetheless offered her the opportunity to represent herself at trial, with appointed trial counsel to serve as standby counsel. Alternatively, Wolford was permitted to retain new counsel provided that any such counsel would be prepared to commence trial the following day. In the circumstances, therefore, Wolford’s second motion to continue the trial was essentially granted in part, as jury selection and further trial proceedings were continued an additional day.

It is well-settled that a petitioner’s right to counsel of her own choosing is not absolute, and that “[a] request for change in counsel cannot be considered justifiable if it proceeds from a transparent plot to bring about delay.” United States v. Gallop, 838 F.2d 105, 108 (4th Cir.1988) (citing Morris v. Slappy, 461 U.S. 1, 13, 103 S.Ct. 1610, 75 L.Ed.2d 610 (1983)). Here, given the trial judge’s express observation that Wolford had engaged in delay tactics, and given that the jury trial had already been delayed once on Wolford’s first motion to continue, it simply cannot be said that the trial judge’s denial of Wolford’s second motion for a continuance amounted to an abuse of discretion.

In sum, then, Wolford’s claim relating to the trial judge’s denial of her second motion for a continuance of the trial is procedurally defaulted. But, even had it been proper to consider this defaulted claim in the instant collateral attack, the claim would nonetheless fail on the merits.

B.

Wolford next argues that trial counsel was constitutionally ineffective during the plea negotiation and pretrial proceedings. Put simply, Wolford contends that had she received competent legal advice from trial counsel in this instance, she would have accepted the plea offer extended by the government in June or August 2006 rather than proceed to trial, thus subjecting her to a significantly lower guidelines range of imprisonment and possibly a lesser custody sentence. Unlike Wolford’s first claim, this ineffective assistance of counsel claim has considerable force.

It is well-settled that “[a] criminal defendant has a right to effective assistance of counsel in deciding whether to accept or reject a proposed plea agreement.” Toro v. Fairman, 940 F.2d 1065, 1067 (7th Cir.1991) (citations omitted). Indeed, “the decision whether to plead guilty or contest a criminal charge is ordinarily the most important single decision in a criminal case ... [and] counsel may and must give