50 East Washington Street
Suite 400
Chicago, IL 60602
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 nearly four 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 client-centered conviction: litigation is not an end in itself but must always be managed to align with and serve his 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 and other Federal Circuits. His practice encompasses a broad spectrum of practice areas and industries, and his clients span Fortune 500 companies, private equity firms, real estate developers, mid-market and emerging companies, and C-suite executives.
Chief Legal Officers 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, for example, he reframed the defense around a single compelling theme that made adjustable-rate mortgage disclosures intelligible and used a methodical cross-examination of the plaintiff to expose the fundamental gap between the claims and the evidence. As a result, Lenny secured a complete defense verdict and affirmance on appeal. His ability to parachute into high-pressure situations, master unfamiliar subject matter rapidly, and deliver in the courtroom 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 has maintained this outlook from the inception of his career at Kirkland & Ellis through his time at Bartlit Beck, a nationally renowned trial boutique that he helped form.
Lenny subsequently served as Deputy General Counsel of Bank One — then a Fortune 100 financial institution later acquired by JPMorgan Chase. He managed several practice groups and oversaw the legal department’s $100 million-plus budget. His in-house tenure reinforced his conviction that outside counsel must understand the client’s business as deeply as its legal position. As a result, Lenny also well understands the internal dynamics of large organizations, the risk calculus that keeps in-house counsel up at night, and the centrality of ensuring that litigation strategies are 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, including cases involving corporate fraud. His criminal 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. His time as a federal prosecutor also 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.”
Representative Matters
Trials and Arbitrations
- Represented JPMorgan Chase in the trial of a $750 million class action in the U.S. District Court for the Central District of California and on appeal in the U.S. Court of Appeals for the Ninth Circuit involving claims under California’s Unfair Competition Law related to adjustable-rate mortgage disclosures; obtained defense verdict and affirmance on appeal.
- Represented a global healthcare company in a $130 million arbitration involving alleged failure to use commercially reasonable efforts to commercialize a product; obtained unanimous defense award after a six-day evidentiary hearing.
- Represented JPMorgan Chase in a $100 million jury trial in Los Angeles Superior Court involving fraud claims brought by two foreign nationals against former business partners; obtained defense verdict.
- Represented a home healthcare and hospice company board member and trustee in a jury trial in Virginia state court involving breach of contract and fiduciary duty claims; obtained defense verdict.
- Represented a Fortune 500 healthcare company in an eight-figure arbitration in Illinois involving an exclusive distribution agreement; settled on confidential terms before final hearing.
- Represented a private equity firm in an $8 million breach of contract arbitration in Chicago, Illinois arising from the sale of a healthcare company; obtained a favorable award for the claimant following a two-week arbitration.
- Represented a steel manufacturer in a $6.5 million Wisconsin state court jury trial involving professional negligence and negligent misrepresentation claims against its actuarial consultant arising from an allegedly flawed valuation that affected the sale of the company. Verdict for the defendant.
- Represented a dental and veterinary imaging company in a nearly $5 million arbitration in Illinois involving an accounting dispute related to a contingent purchase-price earnout; obtained award for claimant.
- Represented relators in state qui tam bench trail against national home improvement retailer over sales taxation of installed residential appliances; successfully obtained favorable judgment and affirmance of liability finding on appeal. Case on remand for damages trial.
- Represented a stone installation company in an arbitration and related federal litigation in the U.S. District Court for the Northern District of Illinois and the U.S. Court of Appeals for the Seventh Circuit involving withdrawal liability under the Multiemployer Pension Plan Amendments Act; secured a complete defense victory at all levels.
- Represented United Airlines in a jury trial in Illinois state court involving sex discrimination and breach of contract claims; obtained defense verdict.
Internal Investigations
- Represented the board of directors of a consumer technology services company in a confidential internal investigation concerning alleged fraud and potential contractual violations.
- Represented the board of directors of a global technology provider in a confidential investigation of allegations about employee misconduct.
- Represented an educational institution in an internal investigation involving allegations of hostile work environment and retaliatory conduct directed at a C-suite officer.
- Represented a real estate investment management firm in an internal investigation involving alleged financial misrepresentations and fund commingling.
- Represented a national healthcare company in an internal investigation involving recordkeeping practices.
- Represented a national insurance company in a confidential internal investigation and related employment dispute involving discrimination and retaliation allegations.
- Represented a former client employee in connection with a grand jury subpoena for documents and testimony relating to a criminal investigation into potential insider trading.
- Represented a client employee in an internal investigation relating to the employment of foreign nationals.
Other Representative Matters
- Represented TIAA in a $1.2 billion defamation and antitrust action in Delaware Superior Court involving alleged reputational and competitive harm; obtained summary judgment.
- Representing the National Association of Realtors in a multi-billion dollar national antitrust class action involving alleged restraints on competition in residential real estate transactions.
- Representing JPMorgan Chase and other financial institutions in multidistrict antitrust litigation in the Southern District of New York and the Northern District of Illinois involving payment card network rules governing interchange fees, including related opt-out damages actions.
- Representing JPMorgan Chase in Circuit Court of Cook County, Illinois in a $170 million fraud and embezzlement dispute involving a decade-long scheme and over a thousand challenged transactions by the bank customer’s CFO.
- Represented the Illinois Department of Insurance, as liquidator of Land of Lincoln Insurance Company, in U.S. Supreme Court and related litigation involving approximately $127 million in unpaid ACA risk-corridor funds and CMS creditor claims; helped secure a victory as part of a broader $12 billion recovery for insurers.
- Represented JPMorgan Chase in multi-million-dollar litigation arising from its provision of banking services to Jeffrey Epstein, including claims brought by the U.S. Virgin Islands seeking at least $190 million in penalties and disgorgement for alleged failures to detect and report suspicious financial activity; settled on confidential terms prior to trial.
- Represented a consumer financing company in a $40+ million multi-forum dispute involving the collapse of a vehicle service contract administrator; obtained summary adjudication awarding full damages and interest in arbitration.
- Represented Union Pacific as co-counsel in multidistrict antitrust litigation involving fuel surcharge practices.
- Represented a former deputy mayor of Chicago, Illinois and senior executive of United Airlines in high stakes litigation in Chicago involving airline gate allocation at O’Hare International Airport.
- Represented the trustees of Unite Here Health in an ERISA class action involving alleged breaches of fiduciary duty; led discovery and dispositive briefing, obtaining summary judgment, partial denial of class certification, and sanctions against third parties.
- Represented Baxter/Allegiance Corporation in a patent infringement action in the U.S. District Court for the Southern District of Ohio involving thermal therapy technology; case dismissed with prejudice and court awarded attorneys’ fees and costs.
- Represented the family of murdered Democratic National Committee staffer Seth Rich in litigation against Fox News arising from allegedly false and defamatory reporting and conspiracy theories surrounding Rich’s death, involving claims for intentional infliction of emotional distress and related torts; resolved through settlement.
- Represented JPMorgan Chase in federal court litigation involving decommissioning of a bank branch and related claims for breach of lease, property damage, and statutory damages; obtained summary judgment and resolved the matter without appeal.
- Represented Pall Corporation in California state court litigation in California involving breach of warranty claims related to municipal water treatment systems; resolved through settlement.
- Represented a national fitness and athletic club in a construction dispute involving the design and installation of a swimming pool facility; secured dismissal with prejudice.
- Represented a global supplier in a federal court action in the Southern District of New York involving breach of contract and unfair competition claims; resolved through settlement.
- Represented two senior executives in a confidential multi-million-dollar compensation dispute in Illinois involving threatened for-cause removal and separation-related economics; resolved through settlement.
Education
- Harvard Law School, J.D., cum laude (1988)
- Dartmouth College, B.A., magna cum laude (1985)
Clerkship
- Hon. James B. Moran, U.S. District Court for the Northern District of Illinois
Awards
- Band 2, Litigation: General Commercial (2022–present), Chambers USA
- Litigation Star (2020–present), Benchmark Litigation
- Chicago Elite, Commercial Disputes (2025–present), Legal 500
- Notable Litigator & Trial Attorney (2025), Crain’s Chicago Business
- Leading Lawyer, Civil Appellate Law and Commercial Litigation (2021-present), Leading Lawyers
- Best Lawyer, Litigation – Banking & Finance (2024-present), Best Lawyers
Admissions
- U.S. Supreme Court
- U.S. Court of Appeals for the First Circuit
- U.S. Court of Appeals for the Second Circuit
- U.S. Court of Appeals for the Third Circuit
- U.S. Court of Appeals for the Fifth Circuit
- U.S. Court of Appeals for the Sixth Circuit
- U.S. Court of Appeals for the Seventh Circuit
- U.S. Court of Appeals for the Ninth Circuit
- U.S. Court of Appeals for the Tenth Circuit
- U.S. Court of Appeals for the Federal Circuit
- Trial Bar for the U.S. District Court for the Northern District of Illinois
- Illinois
Community Service
- 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