Massey & Gail LLP

Founding Partner

Described by clients as an “exceptional trial lawyer” who maintains a “high awareness of the commercial context in which he practices,” Lenny Gail has spent over three decades as a trusted trial lawyer and strategic counselor for some of the country’s largest and most sophisticated clients. Lenny is among the increasingly rare breed of courtroom advocates who can take on and try any kind of case. Yet for all of his courtroom proficiency, Lenny approaches each engagement with a practical conviction: litigation is not an end in itself but must always be managed to align with the client’s broader objectives and interests.

Lenny’s courtroom range is exceptional. He regularly handles jury trials, bench trials, and arbitrations throughout the United States. He has also argued numerous appeals, including in the U.S. Court of Appeals for the Seventh Circuit and other federal circuits. His practice encompasses a broad spectrum of practice areas and industries, and his clients span Fortune 500 companies, financial institutions, healthcare enterprises, private equity firms, real estate developers, mid-market and emerging companies, and C-suite executives.

General counsel turn to Lenny when their thorniest disputes demand a proven trial lawyer — often when other counsel have litigated a case for years and the moment has arrived to shift the dynamics, reshape the narrative, or prepare for trial. When Lenny stepped in to represent JPMorgan Chase in a $750 million class action in California, he reframed the defense around a single compelling theme that made adjustable-rate mortgage disclosures intelligible to the jury, and then used a methodical cross-examination of the plaintiffs’ expert to expose the fundamental gap between the claims and the evidence. As a result, Lenny secured a complete defense verdict and affirmance on appeal. That ability to parachute into high-pressure situations, master unfamiliar subject matter rapidly, and deliver in the courtroom is what separates Lenny from the field. As one client puts it, Lenny has “a piercingly efficient eye for what is critical” and is an advocate they “would trust with any litigation matter.”

Lenny partners closely with in-house legal departments and co-counsel teams — treating every in-house and outside lawyer representing the client as a collaborator working toward a unified goal. Lenny developed that collaborative instinct early in his career as one of the original lawyers who left Kirkland & Ellis to help form Bartlit Beck, one of the country’s premier national trial boutiques.

Lenny subsequently served as Deputy General Counsel of Bank One — then a Fortune 100 financial institution later acquired by JPMorgan Chase. In that role, he managed multiple practice groups and oversaw the legal department’s budget exceeding $100 million. His in-house tenure reinforced his conviction that outside counsel must understand the client’s business as deeply as its legal position. Lenny, as a result, also intimately understands the internal dynamics of large organizations, the risk calculus that keeps general counsel up at night, and the expectation that litigation strategy will be tightly aligned with corporate objectives.

After leaving Bank One, Lenny served as an Assistant United States Attorney in the Northern District of Illinois, where he directed investigations and prosecuted cases involving corporate fraud. His prosecutorial experience — developing a case from the bottom up and mastering granular detail while never losing the arc of the larger narrative —sharpened the forest-and-trees discipline he brings to every matter today. His time as a federal prosecutor informs how Lenny tackles sensitive internal investigations that companies bring to him when they need an objective outside examination conducted with the utmost discretion.

In 2008, Lenny co-founded Massey & Gail with Jonathan Massey, growing the firm into a nationally recognized litigation boutique with offices in Chicago and Washington, D.C. As a Legal 500 client has observed, “M&G is uniquely situated in that it has a solid roster of real trial lawyers with courtroom experience in complex matters. That background ensures that any matter is better handled from inception as they know how the whole movie plays out.”

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

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