Conservative committee blasts Hillsborough Sheriff candidate Brian Boswell

Brian Boswell
The Hillsborough Sheriff's race is getting colorful.

The race for Hillsborough County Sheriff is already heating up and a political alliance is forming around two candidates hoping to unseat incumbent Chad Chronister.

Building a Brighter Future for Florida, a conservative political committee run by Thomas Piccolo of Strategic Image Management, sent a flyer to Hillsborough County voters this week blasting Republican candidate Charles Brian Boswell over his disciplinary record as a detective with the Sheriff’s office.

“Know the real disgruntled Deputy Charles Boswell,” the flyer heading reads above a list of disciplinary action taken against the former Sheriff’s detective.

He was demoted and suspended for “conduct unbecoming,” the flyer asserts.

Boswell served 25 years with HCSO, but was forced out of his position after disciplinary action dating back to 2014 triggered a demotion, reduction in pay, suspensions and, ultimately, his job.

Several allegations against him were sustained, including noncompliance with a direct order of a superior, conduct unbecoming an officer and discourtesy.

Boswell is firing back against what he describes as a political smear campaign, arguing he was the victim of retaliation by the “upper echelon” of the Sheriff’s office.

While Boswell’s disciplinary action came under former Sheriff David Gee’s leadership, Boswell’s attention is now on Chronister.

“I’m willing to do what Chronister is not and that is to tell you what all of this is about. It’s very simple, when I was a detective; I advised against an unconstitutional arrest and later I would not commit perjury during a court proceeding in regards to the same arrest. As a result I was targeted, retaliated against and yes ultimately demoted for my refusal to lie,” Boswell wrote on his campaign Facebook page.


Those arguments are the central theme in a still-pending federal lawsuit Boswell brought against the Sheriff’s office as well as several top officials.

But while Boswell points to nefarious actions by top brass at the Sheriff’s office, the anti-Boswell flyer argues it’s another reason to reject Boswell.

“Ask yourself, how can someone like Charles Boswell be the Sheriff when he’s suing your Sheriff’s Office?” the flyer reads.

It’s an indication of the tone this race is expected to take with Chronister facing Boswell in the Republican primary in August.

It’s also created an otherwise odd political alliance.

Democrat Gary Pruitt, a retired Tampa Police officer with his own troubled past who is also running, came to Boswell’s defense.

“When you’re the Sheriff and you can’t stand on your record, you send out smear post cards, pathetic,” Pruitt wrote on Facebook.

“Shame on you Chad Chronister. You should call Chad and tell him to resign,” he continued, referring to the flyer’s call to action to urge Boswell to drop out of the race, complete with his phone number.

Boswell, who had been supporting Pruitt before he jumped into the race himself, responded.

“Gary, although we disagree politically, as you stated we are both real cops and know how to campaign honorably. Good luck in the election and stay safe,” he wrote.

Both men see trouble at the Sheriff’s office through a series of perceived injustices.

“I Gary Pruitt believe that HCSO has always been subpar to TPD. As a TPD officer, If I yelled for help, I knew backup was not only coming, it was close. I don’t believe HCSO deputies have ever enjoyed that feeling, but they will with me as sheriff,” Pruitt wrote.

“In full disclosure, I have to be honest, you will enjoy the feeling of backup and staffing with Brian Boswell as sheriff as well.”


Boswell previously told Florida Politics that if he is unsuccessful in the primary against Chronister, he will support Pruitt in the general election.

Pruitt previously ran against Chronister in 2018, earning 45% of the vote compared to Chronister’s 55%.

Janelle Irwin Taylor

Janelle Irwin Taylor has been a professional journalist covering local news and politics in Tampa Bay since 2003. Most recently, Janelle reported for the Tampa Bay Business Journal. She formerly served as senior reporter for WMNF News. Janelle has a lust for politics and policy. When she’s not bringing you the day’s news, you might find Janelle enjoying nature with her husband, children and two dogs. You can reach Janelle at [email protected].


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