Richard Chalkey brings extensive legislative affairs and public policy experience from White House roles served in two Presidential Administrations and roles served in U.S. House of Representatives and U.S. Senate.

Richard Chalkey joined Farragut Partners from the Trump Administration, where he served as Special Assistant to the President for Legislative Affairs at the White House from February 2025 to April 2026. During his recent tenure, Chalkey served as a primary liaison to Members of Congress in the U.S. House of Representatives and was part of the President’s legislative team that worked on the successful passage of President Trump’s historic tax, jobs and spending package, the Working Families Tax Cuts Act, also known as the One Big Beautiful Bill Act. As part of the legislative team, Chalkey also worked on the historic legislative passages of the Recissions Act of 2025 and the GENIUS Act.

Additionally in his role, Chalkey interfaced with component offices of the White House and Cabinet and sub-cabinet agency legislative teams as part of White House policy process developments, rollouts, and Congressional engagement strategy. Further, as part of his duties, Chalkey served as the liaison to House Republican Conference and as a legislative affairs liaison to the White House Task Force on Celebrating America's 250th Birthday (Task Force 250).

In President Trump’s first Administration, Chalkey served all four years at the White House – first as the Associate Director of the National Economic Council (NEC), then as the Associate Director of the Office of Legislative Affairs (OLA) and later as the acting OLA Internal Deputy Director. He was part of the President Trump’s Tax Cuts and Jobs Act team, and part of the passage of USMCA and the CARES Act.

Chalkey has served under every White House Chief of Staff of President Trump and most recently under Assistant to the President and Deputy Chief of Staff for Legislative, Political and Public Affairs James Blair, Assistant to the President and OLA Director James Braid, and Deputy Assistant to the President and OLA House Deputy Director Jeff Freeland. In President Trump’s first Administration he served under former National Economic Council Directors: Gary Cohn and Larry Kudlow and former White House Office of Legislative Affairs Directors: Shahira Knight, Eric Ueland, and Amy Swonger. He also served on the Presidential Transition team for each of President Trump’s administrations and was a professional volunteer at the 2024 Republican National Convention in Milwaukee.

With over a decade of experience in Washington, D.C., Chalkey has also worked in various roles in both the U.S. House of Representatives and the U.S. Senate. Outside of government, he has worked for Deloitte, the Premium Cigar Association, and startup companies. Chalkey holds an MBA from the University of Virginia Darden School of Business, a B.S. in Management and Marketing from the Gies College of Business at the University of Illinois at Urbana-Champaign and studied as a U.S. State Department Gilman Scholar at the University of Hong Kong.

Mr. Chalkey is a native of Streator, Illinois.