1. Florida Politics

Two challenge Hillsborough Sheriff Chronister and his eye-popping campaign fund

Hillsborough County Sheriff Chad Chronister speaks at a Nov. 7 news conference about a sting on unlicensed contractors. Chronister and a political action committee created for his campaign raised nearly $700,000 through December.
Hillsborough County Sheriff Chad Chronister speaks at a Nov. 7 news conference about a sting on unlicensed contractors. Chronister and a political action committee created for his campaign raised nearly $700,000 through December.
Published Feb. 4, 2018

TAMPA — When Gov. Rick Scott tapped Chad Chronister last summer to replace retiring Hillsborough County Sheriff David Gee, the former colonel instantly became the candidate to beat.

As Gee's handpicked successor, Chronister immediately had the support of the local Republican establishment and quickly amassed a huge campaign war chest. By the time voters go to the polls in November, he will have been in the post for more than a year, increasing his name recognition among voters all the while.

So far, two other candidates are in the race to challenge Chronister. Both have decades of law enforcement experience but both are political newcomers who face long odds in an attempt to thwart the Sheriff's Office's tradition of grooming successors and setting them up for victory.

"It's definitely an uphill battle," said Gary Pruitt, 50, a former Tampa Police Department corporal running as a Democrat. "Do I think I can win? Absolutely."

The other candidate is Juan R. Rivera, who is running without party affiliation. Rivera, 74, spent 32 years with the CIA, retiring as a senior operations officer.

"I believe that our county's voters must have a real choice on who should be our next sheriff, something that they haven't had in a long time," Rivera said.

A native of Wapakoneta, Ohio, Pruitt moved to Tampa with his mother at 15 and joined the Tampa Police Department in 1990. He worked as a patrol officer for about 15 years, spending time in all three police districts. Later, as an environmental crimes detective, he was assigned to reduce blight in East Tampa.

After retiring in 2015, Pruitt took a job with California-based Professional Security Consultants, the contractor that provides security for shopping center giant the Westfield Corp.

Pruitt said he's running as an outsider to give voters a candidate who would shake up an agency he called "a good ol' boy network." As a self-described "grunt" who has been in the crime-fighting trenches, he said he would act as an advocate for rank-and-file deputies, streamline the agency's upper ranks and improve diversity within the agency, especially the command staff.

Rivera said he wants to use his experience to hone the Sheriff's Office focus on intelligence to prevent crime.

"From my vantage point, the Sheriff's Office is in great need of upgrading in training, public relations, crime prevention and investigation, in particular," he said.

Rivera spent most of his career with the CIA working as a "clandestine operative" supporting the agency's field operations in the region, according to his resume. He came to Tampa in 2002 when he was assigned to U.S. Central Command at MacDill Air Force Base to help in planning the Iraq invasion. For the next four years, he worked with senior staff on counterterrorism efforts with a focus on the wars in Afghanistan and Iraq.

Rivera served as a U.S. Army infantryman in the Vietnam War and received the Bronze Star and Purple Heart, among other commendations, his resume says.

Ione Townsend, chairwoman of the Hillsborough Democratic Executive Committee, said the party hoped to recruit a big name to challenge Chronister — former Tampa police Chief Jane Castor. But Castor, who is rumored to be pondering a bid for mayor next year, has thrown her support behind Chronister, adding her name to the host committee of his campaign kickoff party in October.

Without the firepower that a candidate like Castor would bring, Townsend acknowledged that beating Chronister will be "a huge challenge." She said Pruitt in theory could receive financial help and other support from the party as early as June 22 if no other Democrats get into the race. That's the last day candidates can qualify to run.

"How much support he would get would be truly dependent on him reaching out to grass roots supporters and his fundraising," Townsend said.

By the end of December, Pruitt had raised only the $200 he donated to his campaign, according to the most recent report available from the Hillsborough County Supervisor of Elections. He said he plans to reach out to Democratic party members and ramp up his fundraising efforts.

Rivera has raised $722 in the same period.

Chronister, on the other hand, raised an eye-popping $441,565 between October and December. A separate political action committee created on his behalf, Law Enforcement for Responsible Government, raised another $291,875 through the end of December.

A campaign representative said Chronister was not immediately available for an interview.

Times senior news researcher Caryn Baird contributed to this report. Contact Tony Marrero at or (813) 226-3374. Follow @tmarrerotimes.