Leonard A. Gail

Leonard A. Gail

Leonard A. Gail
Founding Partner

Massey & Gail LLP
50 East Washington Street
Suite 400
Chicago, IL 60602
Office: 312.283.1590
Direct: 312.379.0470
Fax: 312.379.0467

Leonard A. Gail

Lenny has nearly three decades of experience in civil and in 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 Herman Palenchar & Scott, he has led litigation teams 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 trial teams including multi-million-dollar corporate fraud matters.

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


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

Awards, Honors, and Publications

  • Articles Editor, Harvard Journal on Legislation
  • Voted "Debater of the Decade" (1980s) by the National Debate Tournament's Coaches panel

Community Involvement and Teaching

  • The University of Chicago Law School
    • Former Member of Adjunct Faculty teaching High Technology Trial Advocacy
  • The National Association For Urban Debate Leagues
    • Chairman of the Board, Co-Founder, and Former Executive Director
  • 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, Former Board Chairman and Member
  • The Chicago Debate Commission
    • Former Board Member

Representative Matters

  • Successfully defended JPMorgan Chase at trial in the District Court for the Central District of California and on appeal in the United States 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 (Business and Professions Code § 17200) arising from allegedly deceptive adjustable rate mortgage loan disclosures.
  • Representing Pall Corporation in a complex distribution agreement dispute regarding the distributor’s exclusive right to deal the manufacturer’s product in North America.
  • Secured a $6,490,000 jury verdict in the 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. Straitshot Communications, Inc. v. Telekenex, Inc., 2012 WL 727271, W.D. Wash., March 06, 2012 (NO. C10-268Z).
  • Successfully defended a board member of a home healthcare and hospice company and trustee of a related trust in a jury trial in Virginia State court involving breach of contract and fiduciary duty claims.  DeCesare v. DeCesare, et al., CL-2013-11180 (Va. Cir.).
  • Secured an $8MM+ arbitration award in favor a private equity firm in its breach of contract claim with regard to the sale of a healthcare company.  HealthEdge Investment Fund, L.P., et al. v. Paul Gremillion, et al., 2015-CV-259163 (Ga. Sup. Ct.).
  • Secured a nearly $5MM arbitration award in favor of a dental and veterinary imaging company in an accounting dispute with its purchaser regarding the calculation of a contingent purchase price earnout.
  • Successfully defended a stone installation company in arbitration and in the District Court for the Northern District of Illinois in a withdrawal liability dispute under the Multiemployer Pension Plan Amendment Act of 1980, 29 U.S.C. §1381, et seq., with the Laborers’ Pension Fund.
  • Successfully defended a national fitness and athletic club in a dispute regarding its liability for alleged violations of agreements entered into between its contractor and subcontractors.
  • Successfully defended JPMorgan Chase in a case involving an indemnification dispute arising out of the sale of assets to another large financial services company.
  • Successfully defended Pall Corporation in a lawsuit in California state court over the performance of its water filters in a water treatment plant in Bakersfield, California.
  • Successfully defended an aerospace company and its CEO in a dispute with its accountant regarding earnout calculations.
  • Successfully defended JPMorgan Chase in a New York state court dispute regarding its leases with its landlords with regard to multiple branches in New York state.
  • Successfully defended United Airlines in sex discrimination and breach of contract trial in Illinois state court. Lakin v. United Airlines, Inc.
  • Successfully defended Baxter/Allegiance Corporation in the 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. Seabrook v. Baxter/Allegiance.
  • Represented the Illinois Department of Insurance, as Liquidator of Land of Lincoln Insurance Co., in a challenge to the authority of the federal Centers for Medicare & Medicaid Services (part of the Department of Health & Human Services) to act to benefit itself as a creditor without approval of the State liquidation court.