Full opinion text
MEMORANDUM AND ORDER RE: RENEWED MOTION FOR SUMMARY JUDGMENT OF DEFENDANTS AMERICAN GUARANTEE AND LIABILITY INSURANCE COMPANY, ZURICH NORTH AMERICA COMPANY, BROWN & BROWN, INC., BROWN & BROWN OF CALIFORNIA, INC., AND CALSURANCE (DOCKET ENTRY #85); PLAINTIFFS’ CROSS MOTION FOR PARTIAL SUMMARY JUDGMENT (DOCKET ENTRY # 92); DEFENDANTS’ MOTION TO STRIKE PLAINTIFFS’ CROSS MOTION FOR PARTIAL SUMMARY JUDGMENT (DOCKET ENTRY # 99); PLAINTIFFS’ AMENDED CROSS MOTION FOR SUMMARY JUDGMENT (DOCKET ENTRY # 100); AND DEFENDANTS’ MOTION TO STRIKE PORTIONS OF THE AFFIDAVITS OF GREGG CAPLITZ AND ROSALIND HERMAN (DOCKET ENTRY # 103) BOWLER, United States Magistrate Judge. Pending before this court is a renewed motion for summary judgment on the remaining causes of action in the first amended complaint (Docket Entry #28) filed by defendants American Guarantee and Liability Insurance Company (“American Guarantee”), Zurich North America Company (“Zurich North”), Brown & Brown, Inc. (“B & B”), Brown & Brown of California (“BBC”) and Calsurance (collectively “defendants”). (Docket Entry # 85). Plaintiffs Financial Resources Network, Inc. (“Financial Resources”), Financial Family Holdings LLC (“FFH”), Rosalind Herman (“Herman”) and Gregg D. Caplitz (“Caplitz”) (collectively “plaintiffs”) filed a cross motion for partial summary judgment seeking inter alia jury instructions that plaintiffs were insured under a Life Insurance Agents Errors & Omissions Liability Policy (“E & 0 Policy”) against claims made by Rudy K. Meiselman, M.D. (“Meiselman”), that defendants failed to defend and indemnify plaintiffs in connection with the Meiselman’s cross claim and that defendants misled plaintiffs by misrepresenting the coverage under the E & 0 Policy. (Docket Entry # 92). Defendants filed a motion to strike plaintiffs’ cross motion for summary judgment as untimely and as introducing new facts. (Docket Entry # 99). Defendants also filed a motion to strike portions of the affidavits of Caplitz and Herman as containing statements improperly based upon the beliefs of the parties, speculative and conclusory assertions, statements in contradiction with prior pleadings and sworn statements and statements in support of issues barred by issue preclusion. (Docket Entry # 103). The claims subject to the alleged coverage under which American Guarantee and Zurich North had a duty to defend and indemnify originate from a November 2004 civil action (“the Indianapolis action”) filed in this district by Indianapolis Life Insurance Company (“Indianapolis Life”) against Herman, Caplitz, Meiselman and his wife, Hope E. Meiselman, (“the Meiselmans”) and the Financial Resources Network Plan, Inc. Profit Sharing Plan and Trust (“the FRN Plan”). A default judgment was issued in January 2006 on the claims in the complaint as well as those in a cross claim filed by Meiselman (“Meiselman cross claim”). This final judgment ordered inter alia the rescission of life insurance policies on Meiselman and his wife and the return of a $650,297.01 commission previously paid to Caplitz. On appeal, the First Circuit affirmed. Indianapolis Life Ins. Co. v. Herman, 204 Fed.Appx. 908 (1st Cir.2006). Thereafter, in the Indianapolis action, the district court denied a motion by Herman to stay enforcement and correct execution of the judgment. On appeal, the First Circuit affirmed, holding that the default judgment ran against Herman in her personal capacity. Indianapolis Life Ins. Co. v. Herman, 516 F.3d 5 (1st Cir.), cert. denied, 555 U.S. 823, 129 S.Ct. 137, 172 L.Ed.2d 38 (2008). In 2008, Herman, Caplitz, and Financial Resources filed suit in Massachusetts Superior Court (Suffolk County) against Meiselman and various members of his family. Meiselman removed the matter to federal court and the district court dismissed on claim preclusion grounds. On appeal, the First Circuit affirmed. Herman v. Meiselman, 541 F.3d 59 (1st Cir.2008). Count I in this proceeding sets out claims against B & B, BBC and Calsurance for breach of contract by estoppel. (Docket Entry # 28). Counts II through V consist of claims against Zurich North and American Guarantee for breach of contract. Respectively, these claims allege breach of an express contract to defend and indemnify (Count II), breach of an oral contract (Count III), breach of an implied in fact contract (Count IV) and breach of contract by estoppel (Count V). Count II remains only as to the duty to defend and indemnify Financial Resources, Herman and Caplitz against the Meiselman cross claim. (Docket Entry # 72, pp. 28, 38 & 40). Count VI includes claims against all defendants for breach of the implied covenant of good faith and fair dealing. As noted below, this court allowed summary judgment on counts VII, VIII and IX. (Docket Entry # 72, p. 72). PROCEDURAL BACKGROUND Plaintiffs filed this action in June 2009 in Massachusetts Superior Court (Suffolk County). (Docket Entry # 6). In August 2009, defendants filed a timely notice of removal. Shortly after removal, B & B, BBC and Calsurance filed ‘a motion to dismiss the claims lodged against them in the original complaint pursuant to Rule 9(b), Fed.R.Civ.P., and Rule 12(b)(6), Fed. R.Civ.P. In particular, B & B, BBC and Calsurance moved to dismiss the claims for breach of an oral contract to provide insurance (Count I), breach of an implied in fact contract to provide insurance (Count II), breach of contract by estoppel (Count III) and breach of the implied covenant of good faith and fair dealing (Count VIII) due to the absence of an allegation of a contract. In addition to asserting the untimeliness of the contract claims, B & B, BBC and Calsurance moved to dismiss the negligent misrepresentation, fraud and chapter 93A claims as untimely and the fraud claim due to the lack of particularity. They also sought to dismiss the claims brought by plaintiffs, except those asserted by Caplitz, because Caplitz was the only plaintiff seeking the errors and omission insurance at issue. (Docket Entry #8 & 9). The court allowed the motion on counts I and II because plaintiffs had not “alleged an express contract.” (Docket Entry # 24, pp. 3^f & 9). The court also dismissed the fraud claim without prejudice, allowed plaintiffs leave to file a motion to amend to set out the fraud claim with particularity and otherwise denied the motion. On February 9, 2010, this court allowed a motion to amend and denied a motion for reconsideration. (Docket Entry ##28 & 26). In the latter motion, B & B, BBC and Calsurance sought reconsideration of the denial of the motion to dismiss the negligent misrepresentation and chapter 93A counts as untimely and the breach of the implied covenant of good faith and fair dealing count as lacking an enforceable contract. In denying reconsideration, this court advised the parties that: Defendants may renew the arguments on summary judgment based upon a more developed factual record and the different legal standard of review that applies to a summary judgment motion as opposed to a motion to dismiss. See McKenzie v. BellSouth Telecommunications, Inc., 219 F.3d 508, 513 (6th Cir.2000); McAnaney v. Astoria Financial Corp., 665 F.Supp.2d 132, 142-43 (E.D.N.Y.2009); see also Fisher v. Trainor, 242 F.3d 24, 29 n. 5 (1st Cir.2001). Thereafter, American Guarantee and Zurich North filed a motion for summary judgment (Docket Entry #46) on counts II through IX of the first amended complaint. Adopting the arguments in American Guarantee’s and Zurich North’s motion, B & B, BBC and Calsurance also moved for summary judgment. (Docket Entry # 54). Plaintiffs filed a cross motion for partial summary judgment seeking a declaration that “plaintiffs’ claims are not time barred” and that “defendants were obligated to provide coverage to the plaintiffs.” (Docket Entry ## 59 & 60). On November 18, 2010, 754 F.Supp.2d 128 (D.Mass.2010), this court allowed defendants’ motions for summary judgment as to counts VII, VIII and IX and denied them as to counts II through VI. (Docket Entry # 72). In allowing summary judgment on the fraud, negligent misrepresentation and chapter 93A claims as time barred, this court noted that “plaintiffs reasonably should have known that they were injured as a result of defendants’ conduct no later than March or April 2005.” Plaintiffs filed this action in June 2009, after the expiration of the three year limitations period applicable to the fraud and negligence tort claims and the four year limitations period applicable to chapter 93A. This court also denied plaintiffs’ cross motion for partial summary judgment. (Docket Entry # 72). As explained supra, plaintiffs were not entitled to a declaration that their claims were timely and “the record contains sufficient evidence to allow a reasonable jury to find that the [E & O] policy never issued thereby precluding summary judgment in plaintiffs’ favor.” Currently before this court is the renewed summary judgment motion filed by defendants (Docket Entry # 85), the cross motion for partial summary judgment filed by plaintiffs (Docket Entry # 92), the motion to strike plaintiffs’ cross motion for partial summary judgment filed by defendants (Docket Entry # 99), the amended cross motion for summary judgment filed by plaintiffs (Docket Entry # 100) and the motion to strike portions of the affidavits of Caplitz and Herman filed by defendants (Docket Entry # 103). After conducting a hearing on October 5, 2011, this court took the motions under advisement. STANDARD OF REVIEW Summary judgment is designed “ ‘to pierce the boilerplate of the pleadings and assay the parties’ proof in order to determine whether trial is actually required.’ ” Davila v. Corporacion De Puerto Rico Para La Difusion Publica, 498 F.3d 9, 12 (1st Cir.2007). Summary judgment is appropriate when the record shows “there is no genuine issue of material fact, and the moving party is entitled to judgment as a matter of law.” Rule 56(c), Fed.R.Civ.P. “A dispute is genuine if the evidence about the fact is such that a reasonable jury could resolve the point in the favor of the non-moving party.” American Steel Erectors, Inc. v. Local Union No. 7, International Association of Bridge, Structural, Ornamental & Reinforcing Iron Workers, 536 F.3d 68, 75 (1st Cir.2008). “A fact is material if it carries with it the potential to affect the outcome of the suit under the applicable law.” Id. Facts are viewed in favor of the nonmovant. Noonan v. Staples, Inc., 556 F.3d 20, 23 (1st Cir.2009). When “the nonmovant has the burden of proof and the evidence on one or more of the critical issues in the case is not significantly probative, summary judgment may be granted.” Davila, 498 F.3d at 12 (internal quotation marks, citation and ellipses omitted); accord Clifford v. Barnhart, 449 F.3d 276, 280 (1st Cir.2006) (if moving party makes preliminary showing, nonmoving party must “produce specific facts, in suitable evidentiary form, to establish the presence of a trialworthy issue” with respect to each element on which he “would bear the burden of proof at trial”) (internal quotation marks and citations omitted). Defendants submit a LR. 56.1 statement of undisputed facts. Uncontroverted statements of fact in the LR. 56.1 statement comprise part of the summary judgment record. See Cochran v. Quest Software, Inc., 328 F.3d 1, 12 (1st Cir.2003) (the plaintiffs failure to contest date in LR. 56.1 statement of material facts caused date to be admitted on summary judgment); Stonkus v. City of Brockton School Department, 322 F.3d 97, 102 (1st Cir.2003) (citing LR. 56.1 and deeming admitted undisputed material facts that the plaintiff failed to controvert). FACTUAL BACKGROUND Financial Resources is a Massachusetts corporation that administers and maintains the FRN Plan, a qualified 401 (k) pension plan for Financial Resources employees. FFH is the sole stockholder of Financial Resources. Herman wholly owns FFH and is FFH’s sole member. In 1995, Caplitz began working as a contracted agent for Financial Resources. In 2004, Financial Resources hired Caplitz who, among other responsibilities, acted as Indianapolis Life’s agent in issuing insurance policies to employees of Financial Resources. From June 1997 through October 2006 and during his employment at Financial Resources, Caplitz was a contracted agent with Indianapolis Life. In 2002, Financial Resources hired Meiselman as a technical analyst. As an employee of Financial Resources, Meiselman elected to participate in the FRN Plan and executed a tax free rollover of his retirement funds into the FRN Plan amounting to $11,242,853.20. Herman and Caplitz used funds in Meiselman’s account to pay for insurance policies on the lives of Meiselman and his wife. Herman signed two July 2003 applications with the Meiselmans with the FRN Plan as the designated owner rather than either of the Meiselmans. On or about July 30, 2003, Caplitz submitted an application for a $22,000,000 life insurance policy purchased by the FRN Plan on behalf of Meiselman. The policy was effectively purchased on November 23, 2003, and by letter dated November 25, Caplitz and Herman informed Meiselman that they had completed the underwriting and placement of the policy with Indianapolis. By letter dated November 28, 2003, Meiselman wrote to Caplitz to inform him that he did not wish to accept the policy and asked Caplitz to “immediately direct the return by wire of the moneys removed from [his] account.” (Docket Entry # 87, Ex. R). Caplitz responded to Meiselman’s letter the same day, refuting the points Meiselman made and explaining Caplitz’s “executive decision to put the policy in place.” (Docket Entry # 87, Ex. S). Herman avers that as trustee she made the decision to purchase the insurance policy while Caplitz acted as “broker” and “advisor” and had “no control” over her decision. (Docket Entry # 96, ¶ 7). Herman contacted Meiselman on December 6, 2003, refusing to honor Meiselman’s request to cancel the policy. By letter dated December 12, 2003, Wayne Murphy, Esq. (“Attorney Murphy”), who represented Financial Resources and/or Herman, the FRN Plan and Herman, confirmed his clients’ intent to keep the policy in full force and effect. In two letters to Meiselman dated December 30, Indianapolis Life indicated that the policy would remain in effect as per Herman’s instructions. On or about January 5, 2004, Meiselman filed a complaint against Indianapolis Life and Caplitz with the Massachusetts Office of Consumer Affairs and Business Regulation — Division of Insurance (“the Insurance Division”), claiming that Caplitz solicited him to purchase a life insurance policy, that Meiselman decided he did not want the policy, that Caplitz informed him that the order was cancelled and that Indianapolis Life maintained that the policy was in force. The complaint points out that Caplitz and Herman stood to earn several hundred thousand dollars in commissions from the purchase of the policy. (Docket Entry # 87, Ex. V). By letter dated February 12, Caplitz responded to the complaint filed with the Insurance Division. He disputed Meiselman’s claims and offered his own explanation, averring that the Meiselmans “are the insured and not the owners,” that Caplitz’s obligation was to follow the instructions of the policy owner, Herman, and that Herman had acted in the Meiselmans’ best interest. (Docket Entry #87, Ex. W). On May 4, 2004, Caplitz wrote to John Cleavenger (“Cleavenger”), senior vice president for AmerUS Life Insurance Co. (“AmerUS”), Indianapolis Life’s parent company, to follow up on an April 30 telephone conversation he had with Cleavenger regarding a complaint Meiselman filed with Indianapolis Life. In this letter, Caplitz states: Dr. Meiselman’s complaint to Indianapolis Life is his last gasp effort in a series of complaints he has made to attempt to force a concession from me. He filed complaints with the NASD, since dismissed!,] ... the U.S. Department of Labor determined to be baseless and dismissed and the complaint with the Massachusetts Insurance Department that is currently being investigated. (Docket Entry #87, Ex. X). By letter dated June 14, Cleavenger wrote to Herman regarding Meiselman’s request to rescind the Indianapolis policy. In the letter, Cleavenger concluded that the Meiselman policy should be rescinded and that the premiums paid would be returned with interest. (Docket Entry # 87, Ex. Y). As a contracted agent of Indianapolis Life, Caplitz was enrolled in the E & 0 Policy provided by American Guarantee, a subsidiary of Zurich North, for Indianapolis Life insurance agents from July 1, 2001 to July 1, 2004. BBC, a subsidiary of B & B, offered the insurance through Calsurance, a division of BBC. Calsurance acknowledged and approved applications received from Indianapolis Life agents for the policies provided by American Guarantee. Lancer Claims Services, Inc. (“Lancer”), also a division of BBC, provided claims services for the policies. Because Caplitz was enrolling late for the 2003-2004 E & O Policy, he signed a letter on December 8, 2003, representing the following: 1. After a review of my records and the records of those acting under my personal direction and control, I have no knowledge or information of any fact or circumstance, or any allegation, contention or incident which may result in a claim, suit, or arbitration against me or those acting under my personal direction and control. 2. If the representation and warranties in this letter are false, American Guarantee & Liability Ins. Group may, at its sole discretion, void any insurance coverage issued in reliance on these warranties and representations and/or deny coverage for specific claims asserted under such coverage. (Docket Entry # 87, Ex. O). Caplitz then signed an enrollment form for the 2003-2004 E & O Policy on December 9, 2003, representing the following: I have no knowledge of any pending claim or incident that could give rise to a claim under the proposed policy. It is agreed and understood that if any such claim exists, or knowledge or information exists and any claim or action arises therefrom, it is excluded from coverage for which this enrollment form applies. (Docket Entry # 87, Ex. 0). The E & 0 Policy afforded professional liability coverage for life insurance agents such as Caplitz against “[a]ny ‘Claim’ arising out of a negligent act, error or omission of the ‘Insured’ ... in rendering or failing to render ‘Professional Services.’ ” (Docket Entry # 87, Ex. A, § 1(A)(1)). In greater detail, the relevant language of the E & 0 policy provides that: The Company shall pay on behalf of the “Insured” all sums which the “Insured” shall become legally obligated to pay as “Damages” as a result of: 1. Any “Claim” arising out of a negligent act, error or omission of the “Insured”, or any person for whose acts the “Insured” is legally liable, in rendering or failing to render “Professional Services” for others in the conduct of the “Insured’s” profession as a licensed Life, Accident and Health Insurance Agent, Broker, General Agent or Manager, Notary Public or Registered Representative, while there is in effect a contract between the Named Insured and the insurance company named in Item 1 of the Declarations, or its authorized “Broker/Dealer” subsidiary, as applicable. (Docket Entry # 87, Ex. A, § 1(A)(1)). The term “Claim” is defined in the policy as “a written demand received by the ‘Insured’ seeking monetary damages, including the service of suit ... against the ‘Insured’.” (Docket Entry # 87, Ex. A, § 11(C)). The E & 0 Policy defines “Damages” using similar pecuniary language: “ ‘Damages’ shall mean the monetary amounts for which an ‘Insured’ is legally liable, including sums paid as judgments, awards or settlements.... ” (Docket Entry # 87, Ex. N, § 11(D)). The term “Professional Services” is defined in relevant part as “[t]he sale or servicing of: ... (C) Employee Benefit Plans ... including ... Ordinary Pension or Profit Sharing Plans ... and (e) ‘Financial Planning Activities.’” (Docket Entry # 87, Ex. A, § II(J)(1)). The term “Financial Planning Activities” is defined as “the recommendation or preparation of a financial program for a client involving the client’s present and anticipated assets and liabilities, including recommendations regarding saving, investments, insurance, anticipated retirement or other employees benefit.” (Docket Entry #87, Ex. A, § H(L)). The term “Insured” under the policy is defined to include: The Named Insured set forth in Item 1 of the Declarations, including: a. All Agents or General Agents of the insurance company named in Item 1 of the Declarations provided that they are party to an agent contract with the insurance company named in Item 1 of the Declarations. (Docket Entry #87, Ex. A, § 11(F)(1)). Immediately below the words “Named Insured” in item one of the declarations page appears the language, “The Career Agents and Personal Producing Agents of AmerUs Life, Indianapolis Life and Bankers Life of New York.” (Docket Entry # 87, Ex. A). As a contracted agent with Indianapolis Life, Caplitz was therefore a named insured within the meaning of the E & 0 Policy. The term “Insured” also includes: 2. Any corporation, partnership or other business entity which engages in “Professional Services” and which is either owned or controlled by the Named Insured and then only with respect to those operations of the business entity related to the “Professional Services” provided by the Named Insured. 3. Any person acting on behalf of the Named Insured who was or is a partner, officer, director, stockholder or an employee of the Named Insured or Named Insured’s business entity, provided such person is not a party to an agent or broker contract with any insurance company, and then only with respect to “Professional Services” provided by the Named Insured. (Docket Entry # 87, Ex. A, § 11(F)). The policy contains an Awareness Provision (“Awareness Provision”) which reads in relevant part as follows: If, during the “Policy Period,” the Company shall be given written notice of any negligent act, error or omission which could reasonably be expected to give rise to a “Claim” against an “Insured” under this Policy ... then any “Claim” which subsequently arises out of such negligent act, error or omission shall be considered to be a “Claim” made during the “Policy Period” in which the written notice was received. (Docket Entry #87, Ex. A, § V). The term “Policy Period” is defined as “the period from the effective date of this Policy to the expiration date or earlier termination date, if any, of this Policy.” (Docket Entry # 87, Ex. A, § II(I)). The 2002 to 2003 Policy Year E & 0 Plan Highlights (“E & 0 Highlights”), issued each year to policy holders, reiterates the substance of the Awareness Provision, stating: For your protection, the policy also includes an “Awareness Provision.” This allows you to provide written notice of circumstances that could reasonably be expected to give rise to a claim. Then if a claim subsequently arises out of the described circumstances, it will be considered to be a claim during the Policy Period in which the written notice was received. (Docket Entry # 87, Ex. E). The E & 0 Policy contains the following conditions: As a condition precedent to the right of insurance coverage afforded herein, the “Insured” ... which seeks coverage shall: (a) As soon as practicable, but not more than (60) days after the termination of coverage, give to the Company written notice of any “Claim” made against the “Insured” ... during the “Policy Period” .... (b) Immediately forward to the Company ... every “Claim”, notice, summons or other process received directly by the “Insured” ... or by the “Insured’s” ... representatives in the event suit is brought against the “Insured”.... (Docket Entry # 87, Ex. A, § VII(A)). Lynn Johnson (“Johnson”), president of Calsurance and vice president of B & B, and Jeanette Younger (“Younger”), a Calsurance account administrator, suggest that Lancer may have accepted at least a “potential claim” or an “initial report” of claims orally over the telephone. (Docket Entry # 98, Ex. TT, pp. 138-140 & Ex. WW, pp. 18-20). The policy ended on July 1 of each year. The enrollment form for the 2004-2005 E & O Policy allowed “[ajgents with [expiring [c]overage” to “[e]nroll within 30 days of [ejxpiration.” (Docket Entry # 87, Ex. M). In a number of years prior to 2004, Caplitz enrolled after the 30 day time period. From July 2001 until July 2003, Caplitz was enrolled in the E & O Policy and paid the premium annually by credit card. In 2004, Calsurance “did away with that procedure and mandated that a check be sent.” (Docket Entry # 87, Ex. B, p. 79). Caplitz attests that on or about July 30, 2004, he “delivered to Calsurance” an enrollment form as well as check number 2018 dated July 29, 2004, in full payment of the premium in order to enroll in the 2004-2005 E & O Policy. (Docket Entry # 95, ¶ 9). Younger in his deposition, however, states that CalSurance has no record of receiving a July 29, 2004 enrollment form and a premium check on or about July 30, 2004. (Docket Entry # 106, ¶ 32). Caplitz further avers that he “had no knowledge or reason to believe” that his coverage had not been renewed. He further attests that, “no defendant advised me at the end of the policy year ending July 1, 2004,” of a nonrenewal. (Docket Entry # 95, ¶ 12). Caplitz further alleges that on or about August 8 or 12, “as a consequence of escalating disagreements” between himself, Herman and Financial Resources on the one hand, and Meiselman on the other, Caplitz “called and reported these disagreements to Lancer under the ‘Awareness Provision’ of the [E & O] Highlights.” (Docket Entry # 95, ¶ 14; Docket Entry # 94, ¶ 18). By letter dated August 19 to Caplitz, Stephen Casey (“Casey”) at Lancer acknowledged receipt of the potential Meiselman claim. The letter advised that the policy was “effective for the Policy Period of 07/01/2004 to 07/01/2005,” while noting that “this claim is subject to all other applicable terms and conditions of the policy.” It further states that: [a] complete coverage evaluation will be completed on this matter within the next 30 days. If there are any coverage issues that need to be addressed, you will receive notice of those issues under separate cover. In the meantime, American Guarantee considers all rights mutually reserved. (Docket Entry # 97, Ex. N). On October 28, 2004, Meiselman filed a civil action in this district against Financial Resources, the FRN Plan, ■ Herman and Caplitz when Herman allegedly failed to respond to Meiselman’s request to transfer Meiselman’s funds in the FRN Plan into a third party account (“the Meiselman I complaint”). (Docket Entry # 97, Ex. ■ Q). By letter dated October 29, Cynthia Renner (“Renner”), senior director of coverage for Lancer, informed Caplitz that Lancer was in the process of determining whether there was E & O coverage for Meiselman’s claim and that Lancer was unable to confirm Caplitz’s enrollment for the 2004-2005 E & O Policy period. Caplitz then faxed a copy of a check and enrollment form, each dated July 30, 2004, to Renner on November 5. Meiselman’s claims in the Meiselman I complaint were settled by execution of a Release and Settlement Agreement on or about November 19, 2004, under which the parties agreed to transfer Meiselman’s funds in the FRN account into an individual retirement account at Meiselman’s direction. Caplitz states that he forwarded this agreement to Lancer and informed Stanley Robb (“Robb”) at Calsurance about the settlement agreement around that same time. (Docket Entry # 95, ¶ 33). According to Johnson, however, Lancer did not receive the Release and Settlement Agreement until October 10, 2005. (Docket Entry # 106, ¶ 76). On November 23, 2004, Indianapolis Life filed the complaint in the Indianapolis action against Herman, the FRN Plan, Caplitz and the Meiselmans seeking inter alia rescission of the Meiselman insurance policies and recovery of Caplitz’s $650,297.01 commission. (Docket Entry # 97, Ex. T). By email dated November 29, Younger sent Caplitz an enrollment form for retroactive coverage for the 2004-2005 E & 0 Policy year with an individual effective date of August 1, 2004. As a condition of enrollment, Calsurance required that Caplitz sign a letter acknowledging that he was not currently enrolled in the E & O Policy and that he had a “potential gap in coverage” and would have “no prior acts coverage.” (Docket Entry # 87, Ex. DD). Caplitz did not sign the letter and by another letter dated December 3, 2004, Younger informed Caplitz that his coverage would not be renewed and that he would “no longer have coverage”-under the E & O policy “as of the expiration date of [his] last active policy, July 1, 2004.” (Docket Entry # 97, Ex. Y). On December 6, 2004, Caplitz was served with the complaint in the Indianapolis action. (Docket Entry # 98, Ex. YY). On February 9, 2005, Meiselman filed the aforementioned Meiselman cross claim against Herman, the FRN Plan and Caplitz. (Docket Entry # 87, Ex. H). By letter dated February 24, Casey informed Caplitz that, due to a lack of activity, Lancer had closed its file because “it appears that [Meiselman] will not pursue a claim against [Caplitz]” that Caplitz had orally reported to Lancer. (Docket Entry # 87, Ex. I). Lancer thereafter reopened the file after receiving a copy of the Meiselman cross claim in an August 31 email from Meiselman’s attorney. (Docket Entry # 87, Ex. J). On October 10, 2005, Caplitz faxed a copy of the Release and Settlement Agreement signed by Meiselman to Lancer. (Docket Entry # 87, Ex. K). Johnson states that this was the first time these documents were provided to Lancer. (Docket Entry # 87, Ex. G). By letter dated November 22, Lancer told Caplitz that “there has been no further activity” on the Meiselman file, that Lancer was closing his reopened file and that Caplitz should contact Lancer “if circumstances change in any way.” (Docket Entry # 87, Ex. L). Caplitz never contacted Lancer. In 2007, Herman, Caplitz and the FRN Plan brought a legal malpractice suit in Massachusetts Superior Court (Suffolk County) (“the malpractice action”) against Attorney Murphy, the attorney who had represented them in the underlying litigation. (Docket Entry # 87, Ex. CC). In a settlement, Attorney Murphy satisfied the default judgment on the Meiselman cross claim and Meiselman therefore released Herman, Caplitz and the FRN Plan. On December 9, 2010, Meiselman’s counsel filed a satisfaction of judgment of the Meiselman cross claim in the Indianapolis action. (Docket Entry # 87, Ex. BB). Neither Herman, Caplitz nor the FRN Plan paid any money in satisfaction of the default judgment in the Meiselman cross claim in the Indianapolis action. Herman, however, did “pay attorney’s fees” although she could not determine the portion of the alleged $660,000 amount (Docket Entry # 28, ¶ 46) she paid. (Docket Entry # 87, Ex. C, pp. 131-133). On November 11, 2009, Caplitz received a bankruptcy discharge eliminating liability on the judgment in the Indianapolis action including liability on the Meiselman cross claim. On June 23, 2011, the court in the malpractice action issued a decision against Attorney Murphy following a bench trial. (Docket Entry # 87, Ex. CC). The court found that Caplitz did not suffer any damages as a result of Attorney Murphy’s conduct and rejected Caplitz’s testimony that he paid Attorney Murphy $10,000 for legal services at an undetermined time. (Docket Entry # 94, ¶ 49). Specific to the Meiselman cross claim, therefore, Attorney Murphy satisfied the default judgment. Neither Caplitz nor Herman paid any money in satisfaction of the default judgment. Meiselman executed a release and, in any event, a bankruptcy discharge eliminated Caplitz’s liability on the Meiselman cross claim. That said, construing the record in plaintiffs’ favor and as discussed below, Caplitz incurred legal fees to Attorney Cohan after Attorney Cohan entered his appearance on December 21, 2006, in the Indianapolis action. Caplitz also had an agreement with Herman to reimburse her for half of the attorneys’ fees incurred. Finally, Caplitz testified to experiencing a loss of commission income. He assigned the commission to Herman “or an entity of her choosing.” (Docket Entry # 87, Ex. B, p. 80). DISCUSSION Defendants seek summary judgment “on all remaining claims in this case” (Docket Entry # 86, p. 25), in other words, counts I through VI. For purposes of the motion, they assume that the E & O “Policy was issued to Caplitz.” (Docket Entry # 86, p. 2). They do not, however, distinguish the different causes of action in counts I through VII beyond a brief reference to the remaining claims of “breach of contract, whether oral, written or contract by estoppel, and breach of the implied covenant of good faith and fair dealing.” (Docket Entry # 86). Indeed, they fail to identify the remaining counts and they fail to mention any difference in the law or the facts between the causes of action. Defendants move for summary judgment on grounds that Financial Resources and Herman were never insureds under the E & O Policy (Docket Entry # 86, pp. 7-11); that Caplitz was not entitled to coverage under various provisions of the E & O Policy (Docket Entry # 86, pp. 12-20); and that Caplitz has suffered no damages as a result of his lack of coverage (Docket Entry # 86, pp. 20-24). All of the arguments in support of the first two grounds are specific to the language in the E & O Policy as opposed to any oral representation or conduct that might give rise to an estoppel (counts I and V), breach of an oral contract (Count III), breach of an implied in fact contract (Count IV) and breach of the covenant of good faith and fair-dealing (Count VI). In other words, the import of the arguments in the first two grounds centers around the viability of coverage under the terms, conditions and language in the E & 0 Policy. The arguments are therefore specific to Count II because that is the only count based on the written contract, to wit, the E & 0 Policy itself. Accordingly, this court construes the first two grounds as seeking summary judgment only under Count II. The third ground that Caplitz suffered no damages has a more global reach. It is addressed after the discussion of the first two grounds that challenge Count II and the coverage afforded under the terms, conditions and language in the express E & 0 Policy. Plaintiffs seek partial summary judgment for the court to instruct the jury that plaintiffs were insured against the Meiselman cross claim under either the -2003-2004 or the 2004-2005 E & O Policy; that defendants failed to defend or indemnify plaintiffs in connection with the Meiselman cross claim; and that defendants misled plaintiffs by failing to disclose the existence of the Automatic Extended Reporting Period, misrepresenting to plaintiffs that they were not insured and misrepresenting to plaintiffs that coverage would be provided. (Docket Entry # 92). In seeking partial summary judgment and in opposing defendants’ summary judgment motion, plaintiffs rely on their memorandum of law, the affidavit of Herman, the affidavit of Caplitz and the exhibits and deposition transcripts appended to the affidavit of Attorney Cohan. (Docket Entry # 92). Defendants move to strike plaintiffs’ cross motion for partial summary judgment as untimely in violation of this court’s December 15, 2010 scheduling order. (Docket Entry # 99). Defendants also move to strike portions of the affidavits of Caplitz and Herman on grounds that certain statements: (1) “are improperly based upon the beliefs of the parties;” (2) “contain speculative and conclusory assertions;” (3) “contradict prior pleadings and sworn statements;” and (4) “support issues barred by issue preclusion, rendering them irrelevant.” (Docket Entry # 103). Because Caplitz’s and Herman’s affidavits figure prominently in plaintiffs’ opposition to defendants’ motion for summary judgment and plaintiffs’ cross motion for partial summary judgment considered infra, this court initially examines the motion to strike. I. Defendants’ Motion to Strike Portions of the Affidavits of Caplitz and Herman (Docket Entry # 103) Defendants move to strike statements of Caplitz’s (Docket Entry # 95) and Herman’s (Docket Entry # 96) affidavits which: (1) are improperly premised on belief; (2) contain speculative or conclusory statements; (3) contradict prior pleadings and sworn statements; or (4) concern issues barred by issue preclusion. This court addresses each ground seriatim. A. Statements Premised on Belief “An affidavit or declaration used to support or oppose a motion must be made on personal knowledge, set out facts that would be admissible in evidence, and show that the affiant or declarant is competent to testify on the matters stated.” Rule 56(c)(4), Fed.R.Civ.P. (“Rule 56(c)(4)”). Defendants contend that Caplitz and Herman improperly submitted affidavit statements not based on the “personal knowledge” mandate of Rule 56(c)(4). “Motions based upon ‘information and belief do not satisfy the [Rule 56(c)(4) ] standard.” Murphy v. Ford Motor Co., 170 F.R.D. 82, 84 (D.Mass.1997) (quoting Sheinkopf v. Stone, 927 F.2d 1259 (1st Cir.1991)). The second sentence of paragraph 13, as well as the whole of paragraphs 32 and 34 of Caplitz’s affidavit, are explicitly premised on belief. Paragraph two of Herman’s affidavit is also admittedly based on her belief. Consequently, that sentence and those paragraphs are stricken and afforded no weight in opposition to defendants’ motion for summary judgment or in support of plaintiffs’ cross motion for partial summary judgment. B. Conclusory Statements Defendants also argue that Caplitz’s affidavit contains arguments and conclusory assertions based on factual assumptions. “[Ajffidavits may not contain arguments or conclusory assertions” that would not be admissible at trial. Murphy v. Ford Motor Co., 170 F.R.D. at 85; see also Wynne v. Tufts Univ. School of Medicine, 976 F.2d 791, 796 (1st Cir.1992); Sheinkopf v. Stone, 927 F.2d at 1262. To the extent that Caplitz’s affidavit includes such conclusory statements not based upon personal knowledge, those statements will be given no weight in opposition to defendants’ motion for summary judgment or in support of plaintiffs’ cross motion for partial summary judgment. Thus, the first sentence of paragraph 35, the whole of paragraph 36 and the first sentence of paragraph 42 are stricken. C. Statements Contradicting Prior Testimony Defendants further contend that paragraphs 50 and 85 in Caplitz’s affidavit contain statements that are contradictory to Caplitz’s prior deposition testimony and interrogatory answers. Plaintiffs submit that the paragraphs do not contradict the prior deposition testimony. “It is bedrock law in this Circuit that a party cannot vary his ... testimony with an affidavit unless there is an explanation for the variance.” Spilman v. Mosby-Yearbook, Inc., 115 F.Supp.2d 148, 155 (D.Mass.2000); Murphy v. Ford Motor Co., 170 F.R.D. at 85. Absent a satisfactory explanation, a “party opposing summary judgment cannot create a genuine issue of material fact by the simple expedient of filing an affidavit that contradicts clear answers to unambiguous questions in an earlier deposition.” Gillen v. Fallon Ambulance Service, Inc., 283 F.3d 11, 26 (1st Cir.2002); accord Colantuoni v. Alfred Calcagni & Sons, Inc., 44 F.3d 1, 4-5 (1st Cir.1994); Lowery v. AIRCO, Inc., 725 F.Supp. 82, 85-86 (1989) (when party gives “clear answers to unambiguous deposition questions, he or she cannot raise an issue of fact by submitting a subsequent affidavit that merely contradicts the deposition testimony”); see also Chapman ex rel. Est. of Chapman v. Bernard’s, Inc., 167 F.Supp.2d 406, 419 (D.Mass.2001). “Variations in a witness’s testimony and any failure of memory throughout the course of discovery create an issue of credibility,” however, that is properly resolved by the finder of fact. Tippens v. Celotex Corporation, 805 F.2d 949, 954 (11th Cir.1986) (reversing allowance of summary judgment and finding that affidavit was not inherently inconsistent with deposition testimony and should have been considered); accord Hernandez-Loring v. Universidad Metropolitana, 233 F.3d 49, 54 (1st Cir.2000) (“lapse of memory, new sources of information or other events can often explain a revision”). In paragraph 50, Caplitz avers that, “Left without coverage, Herman, FRNI and I hired Attorney Wayne Murphy ... to represent us.” (Docket Entry # 95, ¶ 85). Defendants submit that Caplitz testified at his deposition that Herman, not Caplitz, chose Attorney Murphy to serve as their counsel in the Indianapolis action. (Docket Entry # 104, p. 6). Elsewhere during his deposition, however, Caplitz testified at one point that he chose Attorney Murphy, at another point that Herman chose Attorney Murphy and at another point that “other attorneys were interviewed” in addition to Attorney Murphy. (Docket Entry # 87, Ex. B, p. 208). Caplitz also testified that Attorney Murphy was on a quarterly retainer as opposed to being paid by the hour. The fact that “Herman, FRNI and [Caplitz] hired Attorney” Murphy to represent them in the Indianapolis action, as stated in the affidavit, does not directly or necessarily contradict the prior deposition testimony that Caplitz or Herman chose Attorney Murphy as counsel. Although paragraph 50 raises credibility questions regarding Caplitz and his memory, it is not contradictory with the prior testimony and therefore constitutes part of the summary judgment record. Turning to paragraph 85, Caplitz avers by affidavit that, “Furthermore, although I paid none of those attorneys’ fees, I have an agreement with Herman to reimburse her for half that amount, with interest at 6% per annum. To date, I owe over $900,000 with interest.” (Docket Entry # 95, ¶ 85). In a previous interrogatory, Caplitz stated that he had paid $262,533 in attorneys’ fees to Cohan, Rasnick & Meyerson, LLP and $172,000 in attorneys’ fees to Attorney Murphy and his law firm to defend against the Indianapolis action and the Meiselman cross claim. (Docket Entry # 87, Ex. Z). In December 2006, Attorney Cohan of Cohan, Rasnick & Meyerson, LLP began representing Herman and Caplitz in the Indianapolis action after the default judgment and the appeal. (Docket Entry # 98, Ex. MM, p. 16). At his prior deposition, Caplitz testified to paying Attorney Cohan $50,000, which Caplitz corrected in an errata sheet to $25,000. (Docket Entry # 87, Ex. B, p. 33). Plaintiffs’ admissions to a number of statements in defendants’ LR. 56.1 statement (Docket Entry # 94, ¶¶ 43, 47, 48 & 49) also raise additional credibility issues regarding the amount of damages. The clause in the affidavit statement that “I paid none of those attorneys’ fees” contradicts the above deposition testimony as well as his sworn answer to the foregoing interrogatory. Viewing the affidavit statement in its entirety, Caplitz further states that, “I have an agreement with Herman to reimburse her for half that amount, with interest at 6% per annum. To date, I owe over $900,000 with interest.” (Docket Entry # 95, ¶ 85). The statement is not contradictory with the prior deposition and interrogatory answer. The amount Caplitz owes Herman under an agreement does not contradict the amount he paid in fees to Cohan, Rasnick & Meyerson, LLP to Attorney Murphy. In addition, plaintiff offers a satisfactory explanation, to wit, “what he owes” is “not what he has paid.” (Docket Entry # 105). In sum, this court does not rely on the clause that Caplitz “paid none of those attorneys’ fees” and the statement that Caplitz has “an agreement with Herman to reimburse her for half’ the amount of attorneys’ fees she paid does not contradict the prior sworn statements that Caplitz paid Attorney Cohan $25,000. Paragraph 85 is not stricken and therefore remains as part of the summary judgment record. D. Statements Already Established by Issue Preclusion As a final matter, defendants contend that Caplitz’s affidavit contains statements on issues precluded by prior litigation. See Indianapolis Life Ins. Co. v. Herman, 204 Fed.Appx. 908 (1st Cir.2006). The federal common law of issue preclusion requires that: (1) both proceedings involved the same issue of law or fact, (2) the parties actually litigated that issue, (3) the prior court decided the issue in a final judgment, and (4) resolution of that issue was essential to judgment on the merits. Global NAPs, Inc. v. Verizon New England, Inc., 603 F.3d 71, 95 (1st Cir.2010). The requirements for issue preclusion are met in this instance. In the prior litigation, the First Circuit found inter alia that: It is undisputed that Indianapolis Life required the defendants to submit a statement of the Meiselmans’ financial condition prepared by a certified public accountant (CPA) as part of the underwriting process. Caplitz provided Indianapolis Life with an income verification statement for the Meiselmans purporting to be from CPA James Goodness. At Caplitz’s request, the verification statement was in fact prepared by James Goodness’ son, Daniel, who was not a CPA. Caplitz asked Daniel Goodness to place the verification statement on his father’s stationery and to sign his father’s name so that it would appear to have been prepared by a CPA. There is thus no dispute that Caplitz acted with the intent to deceive Indianapolis Life by submitting an income verification statement for the Meiselmans, which he intentionally misrepresented to have been prepared by a CPA. Indianapolis Life Ins. Co. v. Herman, 204 Fed.Appx. at 909. Paragraphs 19, 20 and 65 to 80 address the same issues of law and fact as those in Indianapolis Life, namely, the legal and factual basis of Caplitz’s insurance coverage for claims alleged in the prior litigation, claims that are vital to a determination of coverage in the case at bar. The parties actually litigated the issues in Indianapolis Life and a final judgment was issued in Indianapolis’s favor. Finally, the First Circuit’s finding of Caplitz’s intentional misrepresentation was essential to a judgment on the merits where Indianapolis Life was seeking rescission of a life insurance policy based on intentional misrepresentation pursuant to Massachusetts General Laws chapter 175, section 186. Caplitz’s assertions in paragraphs 19, 20 and 65 to 80 are thus subject to issue preclusive effect and are stricken. Finally, this court did not rely on paragraphs 19 and 20 of Caplitz’s affidavit in ruling on defendants’ summary judgment motion (Docket Entry # 85). In other words, even considering these paragraphs, it does not alter this court’s decision on the summary judgment motion (Docket Entry #85). II. Defendants’ Motion to Strike Plaintiffs’ Cross Motion for Partial Summary Judgment (Docket Entry # 99) Defendants move to strike plaintiffs’ cross motion for summary judgment (Docket Entry # 92) as untimely in violation of this court’s December 15, 2010 scheduling order. Plaintiffs oppose the motion and maintain that the motion was timely filed. On December 15, 2010, this court held a status .conference at which dates were set for discovery, expert discovery, dispositive motions and responses to such motions. Motions were due July 15, 2011, and responses were due July 29, 2011. On July 15, this court allowed a joint motion extending the time “to file motions for summary judgment” to July 29. (Docket Entry # 83). On July 29, 2011, defendants filed their renewed motion for summary judgment (Docket Entry # 85) and on August 10 this court allowed an assented to motion to extend the time to September 6 for plaintiffs to respond. (Docket Entry #89). On September 6, this court allowed Caplitz’s emergency motion for extension of time to September 12 to respond to defendants’ motion for summary judgment. (Docket Entry # 90). This court further noted there “shall be no additional briefing.” On September 8, plaintiffs not only filed a response to defendants’ motion for summary judgment but also a cross motion for partial summary judgment. (Docket Entry # 92). The motion comes nearly six weeks after the extension to July 29, 2011, allowed to file “motions,” plural, for “summary judgment.” (Docket Entry # 83). Thereafter, plaintiffs filed the amended cross motion for summary judgment on September 19, 2011. This motion was more than seven weeks after the July 29, 2011 deadline. “[L]itigants have an unflagging duty to comply with clearly communicated case-management orders.” Rosario-Diaz v. Gonzalez, 140 F.3d 312, 315 (1st Cir.1998). “The Civil Rules endow trial judges with formidable case-management authority. This authority specifically includes — indeed mandates — setting deadlines for the filing of pretrial motions.” Rosario-Diaz v. Gonzalez, 140 F.3d at 315 (citing Rule 16(b)(2), Fed.R.Civ.P.). “In exercising this power, ‘Trial judges enjoy great latitude.’ ” Id. at 315 (quoting Jones v. Winnepesaukee Realty, 990 F.2d 1, 5 (1st Cir.1993)); accord Tower Ventures, Inc. v. City of Westfield, 296 F.3d 43, 46-47 (1st Cir.2002) (“litigant who ignores case-management deadlines does so at his peril ... when noncompliance occurs, the court may choose from a broad universe of possible sanctions”); see also Rule 16(f), Fed.R.Civ.P. (“on motion or on its own, the court may issue any just orders, including those authorized by Rule 37(b)(2)(A)(ii)-(vii), if a party or its attorney: ... (c) fails to obey a scheduling or other pretrial order”). Plaintiffs improperly rely on Camilo-Robles v. Hoyos for the principle that district courts may consider and grant cross motions for summary judgment in response to a timely filed motion for summary judgment and may do so “without limit of time.” Camilo-Robles v. Hoyos, 151 F.3d 1, 4 (1st Cir.1998). The motion at issue in Camilo-Robles was not a cross motion for summary judgment, as plaintiffs suggest, but rather a timely filed cross motion seeking additional time in which to oppose summary judgment because the plaintiff had been stonewalled during pretrial discovery. Id. at 4. Although the court may, “[a]fter giving notice and a reasonable time to respond, ... grant summary judgment for a nonmovant ... or consider summary judgment on its own,” Rule 56(f), Fed.R.Civ.P., plaintiffs cite no authority to suggest that courts must consider untimely cross motions for summary judgment. Plaintiffs do identify a case where the court entertained such motions filed two and ten days late. Hampshire Community Action Commission v. United Auto Workers Local 2322, 2004 WL 989206, *1 (1st Cir. May 3, 2004). Hampshire, however, involved a significantly shorter period of time after the deadline and simply confirms the discretion and latitude afforded a court to enforce scheduling orders. In the case at bar, as in Rosario-Diaz v. Gonzalez, plaintiffs filed a motion for summary judgment weeks after the expiration of an already extended deadline for filing dispositive motions. Similarly, “they proffered no compelling reason for their delinquency.” Rosario-Diaz v. Gonzalez, 140 F.3d at 315. Plaintiffs also assert that they properly filed their cross motion under Rule 56(f) within the time permitted for their opposition. (Docket Entry # 101). This is neither true nor compelling. Plaintiffs’ amended cross motion was filed under Rule 56(a) and (g), Fed.R.Civ.P., 55 days after the deadline for filing summary judgment motions. Because plaintiffs’ cross motion for summary judgment (Docket Entry # 92) and amended cross motion for summary judgment (Docket Entry # 100) are untimely, they are stricken. To the extent plaintiffs’ memorandum (Docket Entry # 93) supports their opposition to defendants’ renewed motion for summary judgment, however, plaintiffs’ arguments will be considered below. III. Renewed Motion for Summary Judgment of Defendants American Guarantee and Liability Insurance Company, Zurich North America Company, Brown & Brown, Inc., Brown & Brown of California, Inc., and Calsurance (Docket Entry # 85) As previously explained, defendants seek summary judgment on three grounds. This court initially turns to the first two grounds before addressing the third ground, i.e., the absence of damages. The first two grounds are specific to Count II which alleges that defendants breached the express contractual duty in the E & 0 Policy to defend and indemnify Financial Resources, Herman and Caplitz against the Meiselman cross claim. Citing to the E & 0 Policy and relevant case law, defendants argue that Financial Resources and Herman were never insureds under the policy and that Caplitz was not entitled to coverage under either the 2003-2004 E & O Policy or the 2004-2005 E & O Policy. Plaintiffs, in turn, rely upon a substantially different interpretation of the E & O Policy by arguing that the contract language is ambiguous. A. Massachusetts law Under Massachusetts law, “the duty to defend is broader than the duty to indemnify.” Essex Ins. Co. v. BloomSouth Flooring Corp., 562 F.3d 399 (1st Cir.2009) (citing Herbert A. Sullivan, Inc. v. Utica Mut. Ins. Co., 439 Mass. 387, 788 N.E.2d 522, 531 (1997)). Case law provides that: The question of the initial duty of a liability insurer to defend third-party actions against the insured is decided by matching the third-party complaint with the policy provisions: if the allegations of the complaint are “reasonably susceptible” of an interpretation that they state or adumbrate a claim covered by the policy terms, the insurer must undertake the defense. Continental Casualty Co. v. Gilbane Building Co., 391 Mass. 143, 461 N.E.2d 209, 212 (1984); Vappi & Co., Inc. v. Aetna Casualty & Surety Co., 348 Mass. 427, 204 N.E.2d 273, 276 (1965); Magoun v. Liberty Mutual Ins. Co., 346 Mass. 677, 195 N.E.2d 514, 517 (1964); Terrio v. McDonough, 16 Mass.App.Ct. 163, 450 N.E.2d 190, 193 (1983); see also HDH Corp. v. Atlantic Charter Ins. Co., 425 Mass. 433, 681 N.E.2d 847, 850 (1997) (“insurer has a duty to defend if the allegations of the complaint are reasonably susceptible of an interpretation that they state a claim covered by the terms of the insurance policy”). “The scope of an insurer’s duty to defend is ‘based not only on the facts alleged in the complaint, but also on the facts that are known or readily knowable by the insurer.’ ” Timpson v. Transamerica Insurance Co., 41 Mass.App.Ct. 344, 669 N.E.2d 1092, 1095 (1996) (quoting Desrosiers v. Royal Ins. Co. of America, 393 Mass. 37, 468 N.E.2d 625, 627-628 (1984)). “In Massachusetts, as elsewhere, an insurer must defend the entire lawsuit if it has a duty to defend any of the underlying counts in the complaint.” Liberty Mutual Ins. Co. v. Metropolitan Life Ins. Co., 260 F.3d 54, 63 (1st Cir.2001); accord Mt. Airy Ins. Co. v. Greenbaum, 127 F.3d 15, 19 (1st Cir.1997) (“under Massachusetts law, if an insurer has a duty to defend one count of the complaint, it must defend them all”). “[A] duty to defend,” however, “does not exist until it is shown that the person claiming coverage was, in fact, an insured under the policy.” Timpson, 669 N.E.2d at 1094; see Allan D. Windt, 1 Insurance Claims and Disputes § 4:5 (5TH ed.2011). Furthermore, “the insured bears the burden of establishing coverage,” while “the burden is on the insurer to establish the applicability of an exclusion.” Finn v. National Union Fire Ins. Co. of Pittsburgh, Pennsylvania, 452 Mass. 690, 896 N.E.2d 1272, 1275 (2008). Under Massachusetts law, “the interpretation of insurance contracts is generally a matter of law for the court.” Scottsdale Ins. Co. v. Torres, 561 F.3d 74, 77 (1st Cir.2009). Massachusetts courts utilize general rules of contract interpretation to construe an insurance policy. Brazas Sporting Arms, Inc. v. American Empire Surplus Lines Ins. Co., 220 F.3d 1, 4 (1st Cir.2000) (“[u]nder Massachusetts law, we construe an insurance policy under the general rules of contract interpretation”). A policy’s actual language is “given its plain and ordinary meaning” considering “ ‘what an objectively reasonable insured, reading the relevant policy language, would expect to be covered.’ ” Id.; accord National Union Fire Ins. Co. of Pittsburgh, Pennsylvania v. West Lake Academy et al., 548 F.3d 8, 13 (1st Cir.2008) (courts “ ‘begin with the actual language of the policies, given its plain and ordinary meaning’ ” and “ ‘[i]n so doing, we consider what an objectively reasonable insured, reading the relevant policy language, would expect to be covered’ ”) (quoting Brazas, 220 F.3d at 4); see also Scottsdale Ins. Co., 561 F.3d at 77 (courts “ ‘construe the words of the policy according to the fair meaning of the language used, as applied to the subject matter’ ”). Moreover, “every word in an insurance contract ‘must be presumed to have been employed with a purpose and must be given meaning and effect whenever practicable.’ ” Allmerica Financial Corp. v. Certain Underwriters at Lloyd’s London, 449 Mass. 621, 871 N.E.2d 418, 425 (2007) (quoting Jacobs v. United States Fid. & Guar. Co., 417 Mass, 75, 627 N.E.2d 463, 464 (1994)). In giving words in an insurance contract meaning and effect, however, courts should not accord “undue emphasis to any particular part over another.” Boston Gas Co. v. Century Indemnity Co., 454 Mass. 337, 910 N.E.2d 290, 305 (2009). An insurance contract is also examined and construed “ ‘with reference to all of its language and to its general structure and purpose.’ ” Cofman v. Acton Corp., 958 F.2d 494, 498 (1st Cir.1992) (quoting Radio Corp. of America v. Raytheon Mfg. Co., 300 Mass. 113, 14 N.E.2d 141, 143 (1938)); accord In re 604 Columbus Ave. Realty Trust, 968 F.2d 1332, 1357 (1st Cir.1992) (court should consider each phrase and clause in light of all other phraseology); see also Sullivan v. Southland Life Ins. Co., 67 Mass.App.Ct. 439, 854 N.E.2d 138, 142 (2006) (“trial judge erred in relying solely on a dictionary definition of the word ‘single’ and ignoring the consistent language used throughout the policy”). Both the structure and the specific words set out an insurance policy’s meaning. Boston Edison Co. v. F.E.R.C., 856 F.2d 361, 366 (1st Cir.1988); see, e.g., Sullivan, 854 N.E.2d at 142-143 (terms of insurance policy unambiguous when read as a whole and in light of use of similar language on various pages of policy). In the event words of a policy “are not ambiguous, ‘they must be construed in their usual and ordinary sense.’ ” Scottsdale Ins. Co., 561 F.3d at 77; accord Nascimento v. Preferred Mut. Ins. Co., 513 F.3d 273, 276 (1st Cir.2008) (absent ambiguity, words of insurance policy are construed “in their usual and ordinary sense”). An “[a]mbiguity exists when the policy language is susceptible to more than one meaning.” Scottsdale Ins. Co., 561 F.3d at 77; accord George Bukuras v. Mueller Group, LLC, 592 F.3d 255, 262 (1st Cir.2010) (‘“ambiguity requires language susceptible of more than one meaning so that reasonably intelligent persons would differ as to which meaning is the proper one’ ”) (quoting Basis Tech. Corp. v. Amazon.com, Inc., 71 Mass.App.Ct. 29, 878 N.E.2d 952, 958-59 (2008)). “Ambiguous policy terms are construed in favor of the insured.” Scottsdale Ins. Co., 561 F.3d at 77 (citing Hazen Paper Co. v. U.S. Fid. & Guar. Co., 407 Mass. 689, 555 N.E.2d 576, 583 (1990)). That said, “it does not follow that ambiguity exists solely because the parties disagree as to the provision’s meaning.” Brazas Sporting Arms, Inc., 220 F.3d at 5; see Continental Casualty Co. v. Canadian Universal Insurance Co., 924 F.2d 370, 374 (1st Cir.1991). “Nor does the mere existence of multiple dictionary definitions of a word, without more, suffice to create an ambiguity, for most words have multiple