Former Hillsborough County Sheriff Deputy Charles Boswell says he wants to defeat Sheriff Chad Chronister to bring “sanity” and law and order back to the county’s law enforcement agency.

“We can deal with anarchy, or we can deal with law and order. I’m your law and order sheriff,” Boswell told Spectrum Bay News 9 last week.

Boswell cites a number of actions that, he says, Chronister has done (or not done) which have made the agency weaker since 2017, when he became David Gee’s handpicked successor. Boswell also says that the incumbent sheriff is insufficiently conservative to represent the Republican Party in the race.  

But Boswell’s own history with the department gives Sheriff Chronister plenty of fodder to challenge his opponent’s credibility. 

Boswell is “extremely unqualified” to run for the office, Chronister says, citing his inclusion on a “Brady’s List” complied by the Hillsborough County’s State Attorney’s Office of local law enforcement officers who have been the subject of allegations of misconduct.

“What it means is you’ve been proven untrustworthy, where your word has been diminished to the point where you’re unable to testify in court,” Chronister says. “Someone who’s been accused of fabricating confessions and encouraging other detectives to fabricate confessions. I think the largest quality that you must possess when you’re going to be a sheriff is integrity.”

Boswell strongly denies the accusations that led to an internal affairs investigation into his conduct. He says officials from the sheriff’s office fabricated claims against him before he departed while the investigation was ongoing against him in 2017. 

A year later, he filed a lawsuit against more than a dozen HCSO officials, including Chronister and Gee.

“The sheriff’s office leveled false accusations against me when I was a detective,” Boswell says when asked what a voter should make of the allegations against him. “I refused to ratify an unconstitutional arrest. I advised against that arrest. A year later, when I wouldn’t commit perjury in regards to that arrest, I was retaliated against by the very same people who are now running this administration.”

Chronister was hand-picked by Sheriff Gee to succeed him less than a year after Gee was elected to his fourth four-year term as sheriff. Chronister then ran and won a two-year term over Democrat Gary Pruitt in 2018. Now, he is looking to win his first four-year term in office.

The sheriff is proud of what he’s accomplished during his three years leading the agency, referring to his crime reduction strategies, diversion programs and student study programs. He also touts the transparency of his department, citing the recent acquisition of 1,000 new full-time body cameras that were approved by the county commission in June and deputies will begin wearing next month.

But there have been issues that have earned him the scorn from his right flank. 

Responding to calls to reduce the jail population in an effort to prevent COVID-19 from spreading, Chronister released 164 county jail inmates accused of low-level, non-violent crimes in March. One of those inmates, who had been in the Orient Road jail for drug possession and was already eligible for release, was arrested the day after he was released in connection to a murder.

Chronister stands by the decision, though he says he felt horrible after hearing the news.

“At that time, COVID-19 was skyrocketing, and my job was to keep the inmates and the detention personnel safe. And because of the results of the precautionary measures I’ve taken and continue to take, we’ve had no detention personnel that have been affected by COVID-19,” he says. 

“We can’t predict the future behavior of anyone,” he adds. “So as horrible as I feel, I stand behind the decision.”

Boswell notes that incident as part of his bill of particulars on why, he says, Chronister isn’t up for the job.

“We have a sheriff here who has made a serious of missteps, some of which have made national news,” he says. “We have a sheriff who arrests pastors while allowing inmates to go free, without the insight or wherewithal to do background checks. Now, we have a murder that was committed by one of those inmates. We have a sheriff here who clearly wasn’t ready for protests here in Hillsborough County.”

Chronister’s arrest of Pastor Rodney Howard-Browne of The River at Tampa Bay Church for violating the county’s ‘safer-at-home’ ordinance angered many social conservatives in Hillsborough County. However, State Attorney Andrew Warren dropped the unlawful assembly charge, and Chronister has since made up with the pastor, including recently attending Sunday services at the church.

Chronister is dominating in fundraising, having raised more than a million dollars to date, when you combine his regular campaign account and his political committee.

But he’s not taking anything for granted. A political committee supporting his candidacy created a website and distributed mailers that includes links to the Sheriff’s Department’s internal investigations file against Boswell and his opponent’s placement on the Hillsborough County State Attorney’s “Brady List” of local law enforcement officers who “have been the subject of allegations of misconduct.”

The website also chides Boswell for sending a campaign contribution and supporting Chronister’s 2018 opponent.

But it’s Chronister’s previous financial support for Democrats that has become an issue with some Hillsborough County Republicans. The sheriff has sent contributions in the past to Barack Obama, the Democratic National Committee and local state Representatives like Dianne Hart and Fentrice Driskell. 

Chronister responds by saying he’s raised “a ton of money” for many Republicans over the years, and he says that people don’t realize at the local level it’s about the relationships with lawmakers from both sides of the aisle that matters.

“I support the most qualified candidate. And if that happens to be a Democrat who I’ll be working with, then that’s who I’m going to support. But it doesn’t make me any less of a Republican,” he says.

Boswell defends his support for Pruitt, saying he did so in 2018 because Chronister “was so left-wing” and that the Democrat was actually the more conservative of the two candidates in that race.

“So I would rather have a conservative Democrat than a radical left-wing individual who’s posing to be a Republican. Who is not, who in fact is a lifelong Democrat,” Boswell says.

Not true, counters Chronister. He says he became a Republican after David Gee took office and was persuaded by others to change his political affiliation to the same party as the sheriff running the agency.

When asked his thoughts about police accountability, Boswell says that the Minneapolis officers who were on the scene when Floyd died were guilty of “gross constitutional violations,” but then quickly pivots to criticizing the HCSO.

“The parallel here in Chronister’s administration is that you have officers who are violating the law,” he says, arguing that can be countered with accountability and raising the hiring standards for deputies. “I think that’s how you fix the problem,” he says.

Despite Chronister’s huge financial advantage, Boswell contends he has a “grassroots movement” that can fuel him to victory.

“The people are allowed to choose who they want. This is an elected position. We don’t live in a monarchy. I think that Sheriff Chad Chronister’s going to understand that in the very near future,” he says. 

Maybe. Or maybe not. We’ll know more after August 18.