Wiles ran Trump’s 2016 and 2020 campaigns in Florida, helping to put the Sunshine State in his victory column both times. She also helped to score improbable statewide victories for two other Florida Republicans — U.S. Sen. Rick Scott and Gov. Ron DeSantis, though her relationship with DeSantis eventually soured.

Following the victory, DeSantis – who dropped out of the 2024 presidential race and endorsed Trump in January – asked Wiles to help steer the ship through his transition in Tallahassee, appointing her chairwoman of his political committee.