Dispute resolution
Leonard Gail, a founding partner at Massey & Gail LLP, is a seasoned litigator with previous experience as Deputy General Counsel at Bank One. Gail currently represents major clients such as JPMorgan and Unite Here Health. Recently, Gail defended JPMorgan in a $170m embezzlement claim and handles class actions for Unite Here Health, including a case challenging administrative expenses in a multi-employer health plan.
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Profile
Position
Founding Partner
Career
Leonard Gail is a founding partner of Massey & Gail and a nationally recognized trial lawyer with nearly four decades of experience handling sophisticated civil and criminal matters nationwide.
Lenny has tried and argued dozens of notable cases in federal and state courts, representing companies and executives involving antitrust, banking, bankruptcy, constitutional law, contracts, employment, environmental regulation, ERISA, fraud, labor, patent, product liability, professional malpractice, real estate, securities, and technology.
Clients turn to Lenny when disputes require seasoned judgment, strategic clarity, and courtroom credibility. He leads trial teams in high-stakes matters around the country and frequently advises companies facing substantial regulatory, financial, and reputational risk.
Earlier in his career, Lenny was a partner at Bartlit Beck, where he handled complex commercial litigation and trial matters across the country.
He later served as an Assistant United States Attorney, where he directed investigations and prosecuted cases involving corporate fraud matters.
Lenny subsequently joined Bank One, then a Fortune 100 financial institution later acquired by JPMorgan Chase, serving as Deputy General Counsel and Senior Vice President. In that role, he managed multiple practice groups and served as chief financial officer for the company’s Law, Compliance and Government Relations department, overseeing a budget exceeding $100 million.
In 2008, Lenny co-founded Massey & Gail LLP, helping build the firm into a nationally recognized litigation boutique.
Memberships
- Co-Founder, Former Chairman of the Board, Former Executive Director, and Board Member, National Association for Urban Debate Leagues
- Co-Founder, Former Chairman of the Board, and Board Member, The University of Chicago Celiac Disease Center
- Co-Founder and Former Board Member, Chicago Run
- Former Advisory Board Member, Northwestern University School of Communication
- Former Board Member, The Chicago Debate Commission
- Former Board Member, The Chicago Humanities Festival
- Former Board Member, Mt. Sinai Hospital
- Trustee, The Bowe Stewart Foundation
- Trustee, The Steans Family Foundation
Education
- Harvard Law School, J.D., cum laude (1988)
- Dartmouth College, B.A., magna cum laude (1985)
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Key clients
- JPMorgan
- Unite Here Health
Work highlights
Defended JPMorgan Chase against lawsuits by alleged Epstein victims and the U.S. Virgin Islands under the Trafficking Victims Protection Act (TVPA), achieving a favorable settlement and addressing significant legal issues. The case attracted considerable media attention.