Career Background and Political Experience
Wiles began her political career in the 1970s working for Rep. Jack Kemp in his Washington office. She subsequently joined Ronald Reagan's 1980 presidential campaign and served as a scheduler in Reagan's White House and Labor Department. These early positions established her foundation in Republican politics and national governance.
After relocating to Florida, Wiles became a prominent figure in state politics. She advised multiple Jacksonville mayors and worked with Rep. Tillie Fowler before taking on statewide campaigns. Her reputation grew significantly after helping businessman Rick Scott win the Florida governorship in 2010, establishing her as a key strategist in the state's competitive political landscape.
Wiles also worked as a lobbyist for major firms including Ballard Partners (2011-2022) and Mercury Public Affairs (2022-2024), representing clients across various industries. In 2021, she was named CEO of Trump's Save America PAC, where she oversaw significant fundraising growth, with donations increasing from $31.5 million in 2019-2020 to $108.7 million in 2021-2022.
Historic Role as White House Chief of Staff
As White House Chief of Staff, Wiles holds one of the most powerful positions in the Trump administration. The chief of staff controls the White House executive office and maintains close proximity to the president, giving her significant influence over policy decisions and administrative operations. Her selection marked a historic moment in American governance as the first woman to hold this prestigious role.
Wiles' appointment reflects her proven track record in managing complex political operations and maintaining organizational discipline. During the 2024 campaign, she earned respect among Trump's closest allies for her calm demeanor and resolute leadership style. Her ability to navigate high-pressure situations and maintain stability within campaign operations demonstrated the skills necessary for the chief of staff position.
In July 2025, Wiles described her experience in the White House as operating at a superhuman pace, highlighting the demanding nature of her responsibilities. Her role requires managing multiple departments and agencies while serving as a key advisor to the president on critical policy matters and administrative decisions.
Political Impact and Recognition
Wiles' contributions to Republican politics have been recognized across the party. In July 2025, the Republican Party of Florida honored her as the 2025 Statesman of the Year, acknowledging her role in shaping major political victories. Party leadership credited her with being the strategic force behind some of the most consequential political victories in recent American history.
Her career trajectory demonstrates her influence in elevating Republican candidates and shaping electoral outcomes. From her early work on Bush-Quayle in 1988 through Trump's 2016, 2020, and 2024 campaigns, Wiles has consistently played pivotal roles in major political contests. Her strategic decisions and campaign management have directly influenced the political landscape of Florida and the nation.
Despite her accomplishments, Wiles' extensive lobbying background has drawn scrutiny regarding Trump's campaign promise to drain the swamp. Critics note the contrast between her decades-long career as a political operative and lobbyist and the administration's stated anti-establishment agenda, though her supporters emphasize her proven competence and loyalty to the president.