D. Ethan Jeffery

D. Ethan Jeffery

Shareholder, Boston
617 226-3410

About D. Ethan Jeffery

Mr. Jeffery’s practice is focused on representing debtors, trustees, and creditors in complex Chapter 11 cases, and the representation of debtors and creditors in non-bankruptcy restructurings and workouts. Mr. Jeffery has represented debtors, creditors committees, and secured and unsecured creditors in bankruptcy and other insolvency proceedings in courts in most states along the Atlantic seaboard. Mr. Jeffery represents plaintiffs and defendants in commercial litigation in bankruptcy proceedings and other litigation matters relating to the debtor-creditor relationship.

Representative Engagements

Restructuring Matters

  • Represented Creditors’ Committee and Plan Trustee in wind down of 300 bed hospital.  Commenced and prosecuted multi-million dollar lawsuits against former officers and directors of hospital, hospital accounts receivable lender and failed pre-petition acquirer of hospital.
  • Represented the Chapter 11 debtors, importers and sellers of petroleum products in Puerto Rico through a retail chain of approximately 250 franchised service stations.  Obtained confirmation of Plan that provided for equity’s retention of ownership.
  • Represented one of the largest owner-operators of offshore barges worldwide as debtor in consolidated chapter 11 cases. Resolved numerous disputed bankruptcy and bankruptcy-related claims and confirmed contested Chapter 11 Plan.
  • Represented the Chapter 11 debtor, one of the largest off-the-road, truck and specialty tire manufacturers in the United States and Canada.  Effectuated the sale of the debtor’s three business lines in separate sales and confirmed a liquidating plan.
  • Represented the Chapter 11 debtor, a real estate holding company that owned four parcels of real estate on Martha’s Vineyard.  The debtor’s real estate holdings were worth in excess of $25 million and its secured debt, to five different creditors, exceeded $36 million.  Confirmed a plan of reorganization, over the objections of two of the secured creditors, which provided for the sale of two parcels and the restructuring of the debt on the remaining two parcels.
  • Represented multiple debtors who collectively owned and operated an iconic golf club and resort including three golf courses, a 54 room hotel, a clubhouse/event center, and a restaurant on approximately 665 acres in and around Bolton, Massachusetts. Obtained confirmation of plan, through a contested confirmation hearing, that resulted in the sale of the debtors’ businesses for more than $10 million.
  • Represented one of the largest national construction companies as the primary creditor in the Chapter 11 bankruptcy proceedings of specialty structural steel fabricators.  The chapter 11 cases were filed just after the debtors were issued multiple contracts to fabricate the structural steel for a $320 million high rise office building in downtown Boston.  Negotiated a multi-party agreement that resulted in the assumption and timely completion of the contracts with minimal cost over-runs such that the building was completed and delivered on time.  Subsequent agreements were negotiated for the subsequent sale and wind down of the debtors’ businesses.
  • Represented the chapter 11 debtor, the single largest contractor on the so-called “big dig” construction project in Boston that resulted in a confirmed Chapter 11 Plan resolving 14 open “big dig” contracts, numerous other open public works contracts, and over $1 billion in debt.
  • Represented a foreign buyer of U.S. specialty designers and importers of shoe and handbags in chapter 11 proceedings for Modern Shoe Company, LLC and Highline United, LLC.  Acted as the stalking horse in a section 363 going concern sale of the debtors businesses.  Following the sale, represented affiliates of the stalking horse, with claims totaling in excess of $31 million, in litigation, brought by the debtors’ liquidating trustee, which involved both affirmative claims against the affiliates and objections to the affiliates’ claims. A settlement of the litigation was reached that resulted in the payment of millions to the affiliates.
  • Represented the chapter 7 trustee of three affiliated non-profit entities that operated a full service hospital in North Adams, Massachusetts for more than 100 years.  The hospital closed precipitously, leaving much of north western Massachusetts and parts of southern Vermont without a functional emergency room and associated emergency medical care.  Worked with the Massachusetts Attorney General, the indenture trustee for the debtors’ secured bonds, various medical supply vendors and another hospital group to, within a month of the bankruptcy filing, reopen the emergency room, radiology department, hospice care and other necessary emergency care.  Subsequently sold the debtors’ hospital assets, including a full service hospital building, associated equipment, various leases of medical offices and multiple parcels of real estate.  Following the sale of the debtors’ assets, engaged in litigation with the indenture trustee for over $35 million of secured bonds, and ultimately settled the dispute such that a distribution could be made to the debtors’ former employees.
  • Represented real estate holding company with over $50 million in assets in the Chapter 11 case of one of its primary shareholders.  Worked with counsel for the debtor to craft a restructuring that will avoid any risk of the forced sale of the debtor’s interest in Seagate.  The required the resolution, both in Bankruptcy Court and state court, a number of issues with specific real estate holdings that would have a material impact both on the debtor and Seagate.
  • Represented chapter 11 debtors that owned the W Hotel and Residences, a real estate project consisting of a luxury hotel and 122 luxury condominium units.  Confirmed a chapter 11 Plan that provided for payment full to creditors and substantial recovery for equity.
  • Represented telecommunications reseller in its Chapter 11 case.  Sold substantially all of the debtor’s assets and confirmed a liquidating plan.
  • Represented Chapter 11 trustee, who assumed control of the debtors’ operations, negotiated a purchase and sale agreement for the sale of substantially all of the debtors’ restaurant assets.
  • Represented principals in three affiliated real estate holding companies that owned multiple commercial properties.  Successfully confirmed a plan for all three cases that included the consent of the secured lenders.

Non-Restructuring Matters

  • Represented the Federal Court receiver for multiple entities that operated multiple vocational schools in Massachusetts and Maryland.  The case involves the marshalling of the debtors’ assets, dealing with state and Federal regulators, assisting in the completion of educational programs for various students, and interfacing with creditors.
  • Represented pharmaceutical company in out of court workout of over $8 million in debt that resulted in the company’s subsequent solvency within a year of the workout.
  • Represented the Attorney General for the State of Rhode Island in an out of court workout involving distressed healthcare entities.
  • Represented the assignee for the benefit of creditors in the sale of a retail chain with over 40 locations that involved a consensual secured party sale of the retail chain.

Representative Bankruptcy Litigation

  • Acted as special litigation counsel retained by Creditors’ Committee to pursue claims against secured lender bank syndicate.  Successfully resolved suit generating approximately $30 million for unsecured creditors.
  • Counsel to liquidating agent pursuant to confirmed Chapter 11 Plan. Pursued multiple causes of action against defendant group of companies specializing in currency exchange technology which was successfully resolved, resulting in meaningful distributions to creditors.
  • Represented the Chapter 11 debtors, importers and sellers of petroleum products in Puerto Rico through a retail chain of approximately 250 franchised service stations in connection with multiple disputes and contested matters brought by lenders which were ultimately resolved so as to enable the debtors to successfully confirm a Plan that provided for equity’s retention of ownership.
  • Represented six national fitness chain franchisees in the Greater Boston area in their successful Chapter 11 reorganizations.  Resolved claims of multiple lenders and lessors in excess of $10 million, providing a substantial distribution to unsecured creditors.
  • Represented Creditors’ Committee and Plan Trustee multi-million-dollar lawsuits against former officers and directors of hospital, hospital accounts receivable lender and failed pre-petition acquirer of hospital.
  • Represented the Chapter 11 debtors, involving two of Boston’s largest office towers in multiple contested matters including a contested confirmation of the Plan which enabled the debtors to retain ownership, restructure and refinance approximately $700 million of indebtedness.
  • Represented five Chapter 11 debtors engaged in the business of waste collection, transfer, processing, recycling and disposal headquartered in New Bedford, Massachusetts in pursuing their claims against their lender for predatory lending practices and unfair and deceptive acts and practices. The action was settled, resulting in a substantial reduction of the lender’s claims and recovery for creditors
  • Represent the Chapter 11 Trustee of telecommunications companies which operated a multi-level marketing pyramid scheme involving as many as a million participants in a defendant class action against domestic and foreign individuals and entities seeking to recover as a fraudulent transfer the amount that each received from the debtors in excess of the amount each paid to the debtors.
  • Counsel to federal court Receiver of entity that owns and manages solar energy systems throughout New England. Commenced litigation against insiders and others for breach of fiduciary duty and to recover distributions made by the company to shareholders while insolvent.
  • Represented Chapter 11 Trustee of a more than 100 year-old well-known candy manufacturer and distributor in New England, investigating and successfully prosecuting an action against the lender/equity holder, which disallowed more than $150 million of disputed claims and  provided a meaningful recovery to unsecured creditors.
  • Represented Chapter 11 debtors that owned a real estate project consisting of a well-known luxury hotel and 122 luxury condominium units in connection with a contested confirmation hearing.

Non-Restucturing Representative Engagements

  • Represented the owners of limited liability companies which collectively held multiple taxicab medallions in successfully restructuring a material reduction in debts to their lender while shielding their commercial properties from the lender’s claim.
  • Represented a real estate development company in successfully defending multi civil actions seeking to foreclose on the company’s assets and ultimately successfully restructuring millions of dollars of secured debt owed to numerous lenders holding mortgages on properties located through the United States.
  • Represented a company and its owner successfully in a dispute arising from a failed acquisition and the subsequent attempt by proposed buyer who purchased the company’s secured debt to use that debt acquire the company by foreclosing on the company’s assets.
  • Represented a marketing company successfully in defense of a claim that the company had breached a marketing agreement resulting in the plaintiff sustaining millions of dollars in damages.
  • Represented affiliated companies involved in the development, construction and management of affordable housing projects in successfully restructuring their secured debt.
  • Represented numerous closed corporations, partnerships and limited liability companies in ligation concerning breaches of fiduciary duty and buyout of minority owner’s interest.
  • Represented numerous companies in the successful defense of claims by predatory lenders.
Professional Involvement
  • Fellow, American College of Bankruptcy
  • American Bar Association
  • Boston Bar Association
  • American Bankruptcy Institute
  • Chairman, Massachusetts Clients’ Security Board
  • Massachusetts Super Lawyers list for Bankruptcy (2008-2024)
  • Super Lawyers Top 100 list for Massachusetts (2022 and 2023)
  • Massachusetts Super Lawyers Rising Stars (2006)
  • Best Lawyers in America, Bankruptcy and Creditor Debtor Rights/Insolvency and Reorganization Law (2011-2024); Litigation – Bankruptcy (2011-2024)
  • Lawdragon 500 Leading U.S. Bankruptcy and Restructuring Lawyer (2020, 2022 and 2023)
  • Boston Magazine Top Lawyers, Bankruptcy and Workout (2021-2023)
  • Member of Phi Delta, Environmental Law Journal, Villanova University
  • Faculty Member, Massachusetts Continuing Legal Education, Inc.

Areas of Practice


  • University of New Hampshire B.A.
  • Villanova Law School J.D.

Bar and Court Admissions

  • Massachusetts
  • Pennsylvania
  • U.S. District Court, District of Massachusetts
  • U.S. District Court, District of New Jersey
  • U.S. District Court, Eastern District of Pennsylvania
  • U.S. Court of Appeals, First Circuit
  • U.S. Court of Appeals, Third Circuit

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