Matthew J. Flynn

Matthew is a seasoned attorney, strategic advisor, and military officer with extensive political experience and institutional knowledge. He focuses his practice on assisting clients with navigating complex government processes, regulatory environments, government affairs, investigations and enforcement, and government contracting and procurement.

Matthew brings decades of experience in the public sector to Steptoe, leveraging his legal, policy, and political acumen to help clients navigate the complexities of both ends of Pennsylvania Avenue.

During the first Donald J. Trump Administration, Matthew held senior positions within the Executive Branch, including Deputy Assistant to the President and Acting White House Cabinet Secretary, Deputy Assistant Secretary of Defense for Counternarcotics and Global Threats, and Counselor for Land and Minerals Management at the Department of the Interior.

Recently, Matthew served as a policy advisor and instructor for the Trump-Vance Presidential transition team and as an attorney for the 60th Presidential Inaugural Committee.

Government Affairs

Matthew is a long-time Republican aide and a trusted GOP policy advisor and strategist. He has worked on a number of national and state-wide campaigns, the most recent of which was a full-time campaign position with the 2016 Donald J. Trump Presidential Campaign. Matthew is also an active volunteer election attorney with the Republican National Lawyers Association.

Matthew helps clients navigate complex government processes and the evolving regulatory environment. He creates customized strategies to minimize exposure and maximize success in public, private, or classified proceedings.

Investigations & Enforcement

Drawing on his significant experience in government, Matthew provides clients with comprehensive, full-spectrum strategies and guidance regarding the unique legal, political, reputational, and media risks generated by federal government scrutiny. He has successfully represented clients before various government agencies in both investigations and enforcement procedures.

He has also led clients through high-profile public congressional investigations, including negotiating and narrowing the scope of investigations with members of Congress and their staff, complying with and responding to subpoenas and document requests, and preparing clients for depositions, transcribed interviews, and public testimony. He has successfully assisted clients in managing multiple concurrent federal investigations, litigation, and crisis strategy to bring successful resolution.

Government Contracting & Procurement

Matthew represents and advises government contractors on the full-spectrum of government procurement and contracting issues, including business development, claims, disputes, compliance, audits, and investigations. He has assisted clients in identifying gaps and developing compliance programs, and advised contractors on a range of compliance issues as they arise in real time, and defended them against allegations and enforcement actions. Matthew has advised both prime and subcontractors ranging from start-ups to some the most well-known names at the Pentagon and in Washington.

Military Service & Pro Bono

In addition to his work at Steptoe, Matthew currently serves in the North Carolina Army National Guard in the Judge Advocate General's Corps. In his military capacity, he has worked in Europe, Africa, and has deployed to various locations in the Middle East. Most recently he deployed in support of Special Operations Joint Task Force – Operation Inherent Resolve.

Matthew places a high value on his pro bono practice and community involvement. He advises veterans and veterans service organizations over a broad range of issues including serving as the Chair of the American Legion's National Small Business Task Force, Subcommittee on Subcontracting. He also volunteers with the Congressional Hockey Challenge, Shriners Hospital for Children, and Waterfront Church DC's Night to Shine – an annual prom experience held for teens and young adults with disabilities.