Retired 32-year veteran of the Orange County Sheriff’s Office Thomas Stroup has filed to run for Orange County Sheriff, the first major candidate into the contest to succeed Jerry Demings, who has held the job for nine years and is running for mayor this year.

Stroup, 60, a Windermere Republican, retired three years ago as a captain in the Orange County Sheriff’s Office after handling numerous assignments through his career from working at the jail to traffic, and from narcotics to special operations, including a tenure as commander of SWAT, a unit with which he participated in thousands of missions.

Stroup filed Tuesday to run in what still is listed as a 2020 election for sheriff, though that is expected to be moved up to a special election this year once Demings formally qualifies for the mayor’s office race.

The sheriff’s office also is expected to draw the candidacy of Orlando Police Chief John Mina. Stroup said he and Mina know each other well and he called the police chief to let him know he’d be running, and they wished each other the best, vowing respectful campaigns.

Stroup joined the Orange County Sheriff’s Office in 1981 and said his story at that point and since has been one of second chances, a concept that he has since embraced for everyone he’s worked with, including those he’s arrested. As a young man with a GED, Stroup was busting rocks in a quarry and picking tobacco in Kentucky when someone steered him to something better than anything he’d imagined, a chance at a police job. Eventually he returned to Orlando, got hired at the sheriff’s office, moved up through ranks, and obtained more and more education, including a master’s degree from the University of Central Florida.

“My whole life has been about second chances. I try to extend that to others as a rule,” he said.

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