Leonard A. Gail

FOUNDING PARTNER

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Massey & Gail LLP
50 East Washington Street
Suite 400
Chicago, IL 60602

Office: 312.283.1590
Direct: 312.379.0470
Fax: 312.379.0467

Lenny has over three decades of experience in civil and criminal matters involving a wide range of trial, other litigation and counseling services. As a Founding Partner of Massey & Gail and as a Partner with Bartlit Beck, he has led teams working on complex matters nationwide. As Deputy General Counsel and Senior Vice President at Bank One (a Fortune 100 diversified financial services company later acquired by JP Morgan Chase), he managed a wide array of practice groups and served as the Law, Compliance and Government Relations Department’s Chief Financial Officer, with a $100 million-plus budget. And as an Assistant United States Attorney, he directed investigations and led trial teams, including on multi-million-dollar corporate fraud matters.

He has taken to trial or argued on appeal dozens of sizeable matters covering a variety of substantive legal areas. Representative cases have involved antitrust, banking, bankruptcy, constitutional, contract, employment, environmental, ERISA, fraud, labor, patent, product liability, professional malpractice, real estate, regulatory, securities, and technology issues.

  • Harvard Law School, J.D., cum laude, 1988
  • Dartmouth College, B.A., magna cum laude, 1985

  • The Honorable James B. Moran, U.S. District Court for the Northern District of Illinois

  • Illinois
  • United States Supreme Court
  • United States Court of Appeals for the First Circuit
  • United States Court of Appeals for the Second Circuit
  • United States Court of Appeals for the Third Circuit
  • United States Court of Appeals for the Fifth Circuit
  • United States Court of Appeals for the Sixth Circuit
  • United States Court of Appeals for the Seventh Circuit
  • United States Court of Appeals for the Ninth Circuit
  • United States Court of Appeals for the Tenth Circuit
  • United States Court of Appeals for the Federal Circuit
  • Trial Bar for the United States District Court for the Northern District of Illinois

  • Litigation Star (2020-2024) — Benchmark Litigation
  • The Best Lawyers in America, Litigation – Banking & Finance (2024)
  • Leading Lawyer, Civil Appellate Law and Commercial Litigation (2021) – Leading Lawyers Network
  • Super Lawyer, Business Litigation (2012 – present) – Illinois Super Lawyers
  • Articles Editor, Harvard Journal on Legislation
  • Voted “Debater of the Decade” (1980s) by the National Debate Tournament’s Coaches panel

  • Adjunct Faculty teaching High Technology Trial Advocacy, The University of Chicago Law School
  • “Remote Depositions” CLE (August 2020, October 2020)
  • “The False Claims Act – An Overview” CLE (September 2019)
  • “United States Supreme Court October 2018 Term In Review” CLE (August 2019)
  • “How In-House Counsel Can Best Assist Outside Counsel and Assess Their Readiness For Trial” CLE (March 2019)
  • “United States Supreme Court October 2016 Term In Review” CLE (June 2017, July 2017, August 2017, September 2017, December 2017)

  • The Bowe Stewart Foundation Board of Directors, Trustee
  • The National Association for Urban Debate Leagues, Co-Founder, Former Chairman of the Board, Former Executive Director, and Board Member
  • The Chicago Humanities Festival, Board Member
  • The Northwestern University School of Communication, Advisory Board Member
  • The Steans Family Foundation, Trustee
  • Mt.  Sinai Hospital, Former Board Member
  • Chicago Run, Co-Founding and Former Board Member
  • The University of Chicago Celiac Disease Center, Co-Founder, and Former Chairman of the Board and Board Member
  • The Chicago Debate Commission, Former Board Member

  • Successfully represented JPMorgan Chase & Co. in multi-million dollar litigations arising from its provision of banking services to sex offender Jeffrey Epstein. The case settled on confidential terms shortly before trial.
  • Secured summary judgment for Nuveen in over half a billion-dollar defamation case involving the high yield municipal bond market.
  • Successfully represented at trial the relators in a multi-million dollar state qui tam action against a nationwide home improvement company for knowingly failing to collect Illinois sales tax on the purchase of certain installed appliances.
  • Successfully defended JPMorgan Chase at trial in the United States District Court for the Central District of California and in the Court of Appeals for the Ninth Circuit in a case involving a certified class alleging an over-$750 million violation of California’s Unfair Competition Law arising from allegedly deceptive adjustable rate mortgage loan disclosures.
  • Represented filtration, separations and purification product manufacturer in the United States District Court for the Southern District of New York in a complex distribution agreement dispute regarding exclusive rights to deal the manufacturer’s product in North America.
  • Successfully defended JPMorgan Chase & Co. in a two week jury trial in Los Angeles Superior Court where two wealthy foreign nationals claimed they had been defrauded by their former business partners.
  • Secured a $6.49 million jury verdict in the United States District Court for the Western District of Washington after a month-long trial in favor of a telecommunications company in a case involving breach of contract and other state law claims.
  • Successfully defended home healthcare and hospice company board member and trustee of a related trust in a jury trial in Virginia State court involving breach of contract and fiduciary duty claims.
  • Secured an $8 million arbitration award in favor of private equity firm on contract breach claim in connection with the sale of a healthcare company.
  • After being hired less than two weeks before the final arbitration hearing, successfully defended Fortune 500 health care company in eight-figure dispute over exclusive distribution contract.  Matter settled shortly before the arbitration hearing commenced.
  • Secured a nearly $5 million arbitration award in favor of dental and veterinary imaging company in an accounting dispute with its purchaser regarding a contingent purchase price earnout.
  • Successfully defended stone installation company in arbitration with the Laborers’ Pension Fund, in the United States District Court for the Northern District of Illinois, and in the Court of Appeals for the Seventh Circuit in withdrawal liability dispute under the Multiemployer Pension Plan Amendment Act of 1980, 29 U.S.C. §1381, et seq.
  • Represent a national fitness and athletic club in a pool design and construction dispute.
  • Successfully defended JPMorgan Chase in a case involving an indemnification dispute arising out of the sale of assets to another Fortune 500 financial services company.
  • Represented Pall Corporation in a lawsuit in California state court over the performance of its filters in Bakersfield, California, water treatment plant.
  • Successfully defended aerospace company and its CEO in a dispute with its accountant regarding earnout calculations.
  • Successfully defended JPMorgan Chase in New York state court dispute regarding multiple branch leases.
  • Secured a defense verdict for United Airlines in sex discrimination and breach of contract jury trial in Illinois state court.
  • Successfully defended Baxter/Allegiance Corporation in the United States District Court for the Southern District of Ohio in trial of thermal therapy patent infringement case. Plaintiff dismissed case with prejudice after pre-trial conference, and attorneys’ fees and costs awarded to Baxter.
  • Represented the Illinois Department of Insurance, as Liquidator of Land of Lincoln Insurance Co., in Illinois state court and in the United States District Court for the Northern District of Illinois in challenge to the authority of the federal Centers for Medicare & Medicaid Services to benefit itself as a creditor without approval of the State liquidation court.