Charles R. Bennett Jr.

Shareholder, Boston
617 226-3408

About Charles R. Bennett Jr.

Restructuring Representative Engagements:

Mr. Bennett handles complex commercial litigation involving financial institutions, contracts, corporate issues including directors’ and officers’ claims, disputes among members of closed corporations, and insolvency. His current practice focuses on rights and remedies for debtors and creditors in corporate Chapter 11 cases.

He devotes a substantial amount of time to banking and lending litigation; representing borrowers in commercial disputes. Mr. Bennett has tried numerous jury and jury-waived cases concerning business torts, unfair trade practices, and insolvency issues.

Mr. Bennett has appeared in the trial courts of Massachusetts, New Hampshire, Rhode Island, the Massachusetts Appeals Court, the Massachusetts Supreme Judicial Court, numerous U.S. District Courts including for Massachusetts, Rhode Island, New Hampshire, Delaware, and the Southern District of New York, and the U.S. Court of Appeals for the First, Third, and Eighth Circuits, as well as before state and local administrative agencies.

Mr. Bennett formerly served as an Assistant District Attorney for Middlesex County.

Representative Engagements
  • 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-Restructuring 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 Bankruptcy Institute
  • Massachusetts Bar Association
  • Boston Bar Association
  • Massachusetts Super Lawyers list for Creditor Debtor Rights (2006, 2008-2024)
  • Chambers USA, Bankruptcy/Restructuring (Massachusetts) (2004-2023)
  • Best Lawyers in America, Bankruptcy and Creditor Debtor Rights/Insolvency and Reorganization Law (2006-2024); Litigation – Bankruptcy (2017-2024)
  • Best Lawyers in America, Lawyer of the Year, Litigation – Bankruptcy (2020)


  • Boston College B.A., cum laude
  • Boston College Law School J.D.

Bar and Court Admissions

  • Massachusetts
  • Rhode Island
  • New Hampshire
  • U.S. District Court, District of Massachusetts
  • U.S. District Court, District of New Hampshire
  • U.S. District Court, District of Rhode Island
  • U.S. Court of Appeals, First Circuit
  • U.S. Court of Appeals, Federal Circuit

Chambers Ranked in USA 2024


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