Massey & Gail LLP

Massey & Gail LLP is a boutique litigation and counseling firm known for delivering exceptional results in complex, high-stakes matters. Founded in 2009, the firm operates from offices in Chicago and Washington, DC, and serves clients nationwide.

We combine the depth and skill of a large firm with the efficiency and focus of a boutique practice. Our efficient teams are led by senior attorneys who bring decades of courtroom, appellate, and regulatory experience to each matter. Clients turn to us for our strategic thinking, clarity, and unrelenting commitment to their goals.

Our lawyers are recognized by Chambers USA, The Legal 500, Benchmark Litigation, Best Lawyers, and Super Lawyers for excellence in commercial litigation, appellate advocacy, and regulatory matters. We routinely handle disputes involving business torts, contract breaches, intellectual property, healthcare, telecommunications, and financial services.

Whether at trial, on appeal, or in negotiations, we deliver creative, high-impact solutions that align with our clients’ business objectives.

Practice Areas

Commercial Litigation

Number of Partners: 4

Fee-Earners: 8 (Based in Chicago and Washington, DC)

Massey & Gail handles sophisticated commercial disputes, including breach of contract, business torts, trade secrets, and antitrust matters. The firm’s litigation team has defended Fortune 500 companies, national financial institutions, and healthcare providers in complex business cases across multiple jurisdictions. Notably, the firm successfully represented Nuveen Investments in a multi-million-dollar tortious interference suit, securing a favorable result.

Partners Involved: Leonard Gail

Contact: Leonard Gail | +1 (312) 283-1590

Appellate & Supreme Court Advocacy

Number of Partners: 2

Fee-Earners: 4 (Based in Washington, DC and Chicago)

The appellate group, led by co-founder Jonathan Massey, is known for briefing and arguing high-impact appeals before federal circuit courts and the U.S. Supreme Court. The firm provides strategic guidance on legal positioning and error preservation from the trial level through final appeal. Its lawyers have helped shape precedent in constitutional, administrative, and commercial law.

Partners Involved:Jonathan Massey

Contact:Jonathan Massey | +1 (202) 652-4511

Regulatory & Administrative Law

Number of Partners: 2

Fee-Earners: 3 (Based in Washington, DC)

Massey & Gail represents businesses and organizations in proceedings involving federal and state agencies. The firm provides counsel on regulatory compliance, rulemaking, enforcement defense, and challenges to agency actions. Clients span industries such as healthcare, telecommunications, and financial services. The firm has filed amicus briefs and white papers in key regulatory cases nationwide.

Partners Involved: Jonathan Massey

Trials & Arbitration

Number of Partners: 3

Fee-Earners:5 (Based in Chicago)

The firm’s trial lawyers have handled jury and bench trials in both state and federal courts, as well as before arbitration panels. From complex fraud claims to cross-border commercial disputes, the firm builds compelling cases supported by meticulous preparation and expert presentation. The team has achieved successful verdicts and settlements for major corporations and public entities.

Partners Involved: Leonard Gail

Strategic Counseling & Risk Management

Number of Partners:2

Fee-Earners: 2 (Based in Chicago)

Massey & Gail provides preventive legal advice designed to avoid litigation, reduce risk exposure, and align legal strategy with business objectives. The firm advises on internal investigations, contract structuring, governance matters, and litigation strategy across sectors. This practice often supports clients involved in ongoing disputes or regulatory challenges.