Gregory P. Deschenes

Greg Deschenes has over 30 years’ experience handling complex commercial litigation, with an emphasis on all aspects of insurance-related litigation. Representing major insurance companies and insurance guaranty funds in state and federal courts across the country, Greg has prevailed at trial and the appellate level in cases involving property and casualty insurance coverage, bad faith, insurance insolvency and class actions.

What do you focus on?

Coverage Disputes

For more than three decades I’ve litigated insurance coverage disputes involving environmental and toxic tort, construction defect, catastrophic losses, advertising injury and personal injury, directors’ and officers’ liability, business interruption, life and disability insurance claims.

Insurance Insolvency

I represent a number of insurance guaranty funds in coverage litigation and disputes with receivers of insolvent insurers.

Bad Faith

I’ve defended insurers against a variety of bad faith lawsuits, including both first-party insurance and third-party bad faith claims. In New England, I’ve acted as regional counsel for a Fortune 200 property and casualty insurance company in the defense of major environmental insurance coverage and bad faith/extra-contractual liability lawsuits.

Complex Commercial Litigation

I have significant experience defending products liability, environmental, securities fraud and complex business litigation cases.


I also have extensive appellate experience and have successfully represented clients in cases before the First Circuit Court of Appeals, the Massachusetts Supreme Judicial Court, the Connecticut Supreme Court, the Maine Supreme Judicial Court, the New Hampshire Supreme Court and the Rhode Island Supreme Court.

What do you see on the horizon?

The insurance industry faces a number of challenges managing emerging risks posed by new technologies such as data security breaches and cyberattacks, AI and driverless vehicles, climate change and pandemics, and other catastrophic events.

Representative cases

  • Representing an insurance guaranty fund, we prevailed at trial obtaining a $48.9 million judgment. In this reinsurance dispute, the guaranty fund presented a claim to the Midland estate for reimbursement of a settlement the guaranty fund had entered into with an insured involving hundreds of thousands of asbestos bodily injury claims. At trial, the reinsurers attempted to second-guess the guaranty fund’s settlement with the insured, alleging that the settlement was not entered into in good faith and on a reasonable basis. After several days of trial, the reinsurers withdrew their objections to the guaranty fund’s claim, resulting in the claim being allowed in full, including attorney’s fees and costs. In the Matter of the Liquidation of Midland Insurance Company, Supreme Court of the State of New York, County of New York, IAS Part 7, Index No. 41294/86 (2013).
  • Representing several insurance guaranty funds, we successfully resolved a $25 million claim against a policyholder. We sought reimbursement of amounts paid by the guaranty funds on the ground that the policyholder had failed to exhaust coverage under a solvent insurance policy before seeking recovery from the guaranty funds. Reliance Insurance Company in Liquidation v. Aramark Corp., May Term, 2012 No. 1356 (Pa. C.P., Phl. Cty.)
  • Represented insurance guaranty fund in asbestos bodily injury coverage action and prevailed at trial on a defense that one of the insured’s excess liability policies was void by reason of having been procured by misrepresentation. On appeal, the Massachusetts Supreme Judicial Court affirmed the trial court’s misrepresentation decision, voiding the policy and further held that coverage under other policies was triggered by inhalation of asbestos fibers during policy period, not by bodily injury during policy period, rejecting the insured’s argument that “exposure in residence” triggered coverage. A.W. Chesterton Co. v. Massachusetts Insurers Insolvency Fund, 445 Mass. 502 (2005).
  • Represented insurance guaranty fund in coverage litigation brought by utility seeking coverage for environmental cleanup costs for former manufactured gas plants in Lynn, Salem and Malden, Massachusetts. Issues addressed included owned property exclusion, application of aggregate limits, allocation and settlement credits, exhaustion and trigger of coverage. A primary focus of the case involved extensive fact and expert discovery concerning sources and effects of contamination during and after the 1800s to support a denial of coverage based on lack of a fortuitous loss. Obtained a ruling that fortuity is an implied requirement of all insurance policies (including those not containing an express expected/intended occurrence definition), and that the insured bears the burden of proving that the loss at issue was neither expected nor intended. Massachusetts Electric Co., et al. v. Commercial Union Insurance Co., et al., Worcester Superior Court, Commonwealth of Massachusetts, C.A., No. 99-00467B.
  • Represented a major life insurance company in a “vanishing premium” case by defeating a motion for nationwide class certification in the federal district court for the District of Massachusetts. Even though the same court had granted class certification against another insurer in an earlier “vanishing premium” case, we persuaded the court that, based on the facts of this case and established federal precedent, the court should deny the plaintiffs certification of a nationwide “vanishing premium” class for trial. Kent v. SunAmerica Life Ins. Co., 190 F.R.D. 271 (D. Mass. 2000).

Representative appellate experience includes the following:

  • Massachusetts Insurers Insolvency Fund v. Berkshire Bank, 475 Mass. 839 (2016) (reversing trial court’s summary judgment ruling and holding that the Massachusetts guaranty fund is entitled to recover workers’ compensation benefits paid to claimant on behalf of high net worth insured).
  • Massachusetts Care Self-Insurance Group, Inc. v. Massachusetts Insurers Insolvency Fund, 458 Mass. 268 (2010) (upholding trial court’s summary judgment ruling that a workers’ compensation self-insurance group is barred from recovering from the Massachusetts guaranty fund because such a group is a member of the insurance industry and thus its claim is not a “covered claim” within the meaning of G.L. c. 175D, § 1(2)).
  • A.W. Chesterton Co. v. Massachusetts Insurers Insolvency Fund, 445 Mass. 502 (2005) (reversing trial court’s ruling and holding that trigger of coverage under excess liability policies is inhalation of asbestos fibers and not bodily injury or exposure in residence).
  • Liberty Mut. Ins. Co. v. SCA Services, Inc., 412 Mass. 330 (1992) (reversing trial court’s grant of summary judgment and holding that the insurers had no duty to defend the insured in a hazardous waste action because the underlying complaint alleged that the damage was caused by waste disposal activities occurring continuously over a protracted period of time as part of regular business activities and therefore did not state a claim within the “sudden and accidental” exception to the pollution exclusion).
  • Connecticut Insurance Guaranty Association v. Drown, 314 Conn. 161 (2014) (holding an insurer’s breach of its duty to defend a medical malpractice suit before becoming insolvent does not bar the Connecticut guaranty association from contesting its obligation to pay a claim made under the insolvent insurer’s policy and that the underlying claim was barred by the policy’s vicarious liability exclusion).
  • Reliance Ins. Co. v. Aramark Corp., 38 A.3d 958 (Pa. 2011) (holding that non-duplication of recovery provision in guaranty fund act required that employer, which asserted it was not a “claimant,” exhaust coverage under solvent contingent liability policy before seeking recovery from the guaranty fund, and that the requirement to exhaust entire $25 million policy limit applied even though employer had recovered only $20.7 million in settlement with insurer).
  • In Re: Joint Petition of Special Deputy Receivers of Doctors Insurance Reciprocal, Risk Retention Group, Virginia State Corporation Commission, Case No. INS-2003-00092 (2008) (rejecting risk retention groups’ claim seeking policyholder-level priority in the Reciprocal of American estate based on assertions of constructive trust, piercing the reinsurance veil and implied cut through).
  • In Re: Application of Reciprocal of America and The Reciprocal Group For a Determination Whether Certain Workers’ Compensation Insurance Policy Payments May Be Made to Claimants Formerly Covered by SITs and GSIAs, Virginia State Corporation Commission, Case No. INS-2003-00239 (2005) (rejecting hearing examiner’s recommendation, reversing the Commission’s prior decision and holding that under the Virginia insurance liquidation statute the receiver of an insolvent insurance company is not permitted to pay certain workers’ compensation claims at 100% and create a super-priority for workers’ compensation policyholders and that all policyholder-level claims must be “apportioned without preference.”)
  • Truk-Away, Inc. v. Aetna Cas. & Sur. Co., 723 A.2d 309 (R.I. 1999) (affirming summary judgment for insurers with policies that had expired by 1974 where there was no evidence showing that property damage triggering coverage had taken place at hazardous waste landfill prior to 1977).
  • Central Maine Power Co. v. Moore, 692 A.2d 943 (Me. 1997) (holding insured’s response costs to comply with consent decrees to remediate pollution were not covered as “damages” under excess liability insurance policies).


Greg has participated as a faculty member in many continuing legal education programs and has published numerous articles on litigation and insurance topics, including the following:

  • “The Differences and Similarities in Dealing with Primary vs. Excess Carriers” (with Kurt M. Mullen), presented at the Mealey’s All Sums: Reallocation & Settlement Credits Conference (November 2006)
  • “Determining the Insurer’s Response” (with Kurt M. Mullen), 1 New Appleman Insurance Law Practice Guide 11-1 (Mathew Bender & Co., Inc. 2007)
  • “Insurer Insolvency” (with Joseph C. Tanski) in Massachusetts Liability Insurance Manual 15-1 (3rd Edition 2017)


  • “Guaranty Fund Case Law Update,” NCIGF Legal Seminar, Denver, CO, June 26, 2019


Gregory P. Deschenes



Phone: 617-345-1324

Fax: 866-947-1653

University of Virginia, J.D.

Brown University, B.A., magna cum laude, Phi Beta Kappa


U.S. Court of Appeals, First Circuit

Gregory was selected, through a peer-review survey, for inclusion in The Best Lawyers in America® 2022 in the field of Insurance Law. Gregory has been listed in Best Lawyers since 2014.

  • American Bar Association
  • Boston Bar Association
  • Defense Research Institute
  • Phi Beta Kappa
  • Alumni Association of Thayer Academy (Braintree, MA); served on board of trustees and as president
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