[citation needed] Crosby was heavily involved in Republican Party politics during his career, serving at one time as a congressional district chairman.

[citation needed] In 2003, Crosby was appointed by Florida Governor Jeb Bush as Secretary of the Department of Corrections, overseeing a budget of $2 billion.

[citation needed] On February 10, 2006, Crosby resigned as Secretary of the Florida Department of Corrections at the request of Governor Bush.

[citation needed] In October 2021, Crosby bergan to serve as the elected City Clerk of his hometown of Starke, Florida.

[citation needed] On March 5, 2024 WCBJ (News 20) reported Crosby resigned after the Florida Department of Law Enforcement conduced a raid of the Stake City Hall as part of an investigation into election issues.