Massey & Gail

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Persuasive Advocates for Complex Disputes.
Persuasive Advocates for Complex Disputes.
Persuasive Advocates for Complex Disputes.
Persuasive Advocates for Complex Disputes.

Massey & Gail LLP is a litigation boutique focused on complex commercial disputes nationwide. Led by former U.S. Supreme Court clerk Jonathan Massey and veteran trial lawyer Lenny Gail, the firm represents companies and executives in high-stakes matters across federal and state courts. With offices in Chicago and Washington, D.C., the firm handles trial and appellate work across industries, including financial services, health care, retail, and private equity. Clients from global brands to closely held businesses rely on disciplined strategy and persuasive courtroom advocacy.

“They combine technical excellence with real creativity.”

Chambers USA Client Quote

“Without exception, the lawyers are smart, nimble and great at synthesizing complex information. They are fast and responsive.”

Chambers USA Client Quote

“Massey & Gail has experienced leadership, is creative, and stays engaged with its clients.”

Chambers USA Client Quote

“The strength of the team is incredible. They are insightful and great listeners. They are also practical.”

Chambers USA Client Quote

“Massey & Gail is a small and nimble firm that is able to handle extremely complex matters more efficiently than bigger firms.”

Chambers USA Client Quote