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Ingram – Eight Reasons to Think Twice About Voting for Chad Chronister for Sheriff

July 31, 2020

Opinion By: Chris Ingram

Incumbent Hillsborough County Sheriff Chad Chronister is up for reelection. In his first election in 2018, after being appointed by the governor to succeed retiring Sheriff David Gee, Chronister barely defeated an unknown and underfunded candidate by just nine points – someone whom he should have clobbered by twenty points or more.

This year, Chronister faces a qualified Primary Election opponent in Charles Boswell (whom I have recommended) and will face two legitimate candidates in November (one Democrat, and one NPA), should he defeat Boswell on August 18.

On paper, Chronister looks like the favorite through November. He looks like the part of modern-day sheriff as though he stepped right out of Hollywood casting. He has raised almost ten times the amount of money of Boswell. He is well-connected, having married into the family of Eddie De Bartolo (a developer and former owner of the San Francisco 49ers). Chronister also has the support of many local “movers and shakers.”

But conservative Republicans have reason to pause and question their support for Chronister on partisan and ideological matters, and General Election voters have reason to think twice about voting for him on several judgment concerns.

Those concerns are:

1).  Chronister is a flip-flopping opportunist. The former Democrat is running again as a Republican, but his background of support shows he still is a Democrat at heart. Chronister has given tens of thousands of dollars to Democrats including $15,000 to Barack Obama for President, and thousands to such assorted partisan Democrats including: Congressman Charlie Crist, Mayor Jane Castor, and Congresswoman Kathy Castor. Chronister has also contributed at least $5,000 to the Democrat National Committee. In short, for someone with an “R” after his name, he looks curiously like a wolf in sheep’s clothing.

FEC reports show Chronister has donated tens of thousands of dollars to Democrats including $15,000 to Barack Obama.

2).  Chronister has repeatedly shown poor judgment as sheriff. Earlier this year, the Sheriff’s Office released an inmate named Joseph Williams who was freed in a coronavirus purge. No one at the Sheriff’s Office reviewed Williams’s lengthy arrest history, which consists of 35 prior charges before showing him to the jail exit. The day after his release, Williams was charged with another crime – this time for murder. Chronister later deflected blame for the release by saying, “There is no question Joseph Williams took advantage of this health emergency to commit crimes while he was out of jail awaiting resolution of a low-level, non-violent offense.” Actually Sheriff, Williams probably is not sophisticated enough to take advantage of anything, but Williams’ alleged murder victim is dead because of mismanagement of the Hillsborough County Sheriff’s Office of which you are the leader.

Joseph Williams was let go due to concerns about the coronavirus spreading in the jail. No one at HCSO reviewed his lengthy arrest record before letting him out. He is alleged to have murdered someone less than 24 hours after Chad Chronister’s agency freed him. Photo courtesy HCSO.

3).  Chronister’s poor judgment is not limited to releasing unchecked dangerous criminals on the citizens of Hillsborough County. At the beginning of the corona virus outbreak, Chronister, as a member of the county’s Emergency Policy Group, voted to institute a county-wide curfew because small population groups in the county were violating county orders to not gather in large groups. The curfew would not have been necessary, had Chronister and other law enforcers merely enforced the existing order. Instead, Chronister chose the easier route by supporting a blanket county-wide curfew order to address the lowest common denominators amongst us whom Chronister and his deputies could not control. Chronister and the EPG quickly reversed themselves by rescinding the curfew following citizen outrage over the measure. In short, after trampling on law-abiding citizens’ rights, wind-testing the electorate seems to be more like Chronister’s preferred style.

4).  Religious liberties are also not a primary concern of Chronister’s. The sheriff, along with liberal Democrat State Attorney Andrew Warren shut down the River of Tampa Bay Church and arrested Pastor Rodney Brown for holding Sunday services in late March. Of Chronister, Brown told local media, “It will be on his record that he shut down a body of Christ, shut down a food ministry that feeds up to 1,000 families every week.” Browne’s arrest prompted Gov. Ron DeSantis to exempt churches, synagogue, and other houses of worship in a statewide order. Charges against Brown were later dropped, and after seeing the handwriting on the wall, Chronister tried to make nice with the good pastor by paying him a personal visit.

Pastor Rodney Brown’s mugshot. Photo courtesy HCSO.

5).  Chronister uses public dollars to shamelessly promote himself. Chronister’s name has been plastered all over county-owned Sheriff’s Office property. Everything from patrol cars, to computers and buildings, to face masks, and forklifts, nothing it seems is exempt from Chronister’s narcissism and a “Sheriff Chad Chronister” sticker being slapped upon it. But Chronister’s most egregious waste of taxpayer dollars was running television advertisements featuring the sheriff soliciting the public to join the employ of the HCSO. Got that? They ran TV ads – nearly $50,000 worth of them – to find recruits. When was the last time you saw any employer going to the television airwaves to find employees? Rarely. Apparently, Chronister has not yet discovered LinkedIn, Indeed, or other job boards most employers use. In addition to squandering almost $50,000 for this self-promotion (the ad featured Chronister talking to the camera), the ad agency for the jobs TV ad was selected in a no-bid contract, and was awarded to an out-of-state agency – because apparently there are not any agencies in Hillsborough qualified to do an ad buy. Was it effective? You decide. The Sheriff’s Office says employment applications increased by just eight (8) people in May 2020 (the month the TV ads began running), over the year before.  June 2020 numbers doubled from the same period over 2019.

Good thing everybody who sees that forklift knows Chad Chronister is the Sheriff.

6).  At the height of the Black Lives Matter riots, anarchists assembled at the Hillsborough County Jail on Orient Road and began to rip down the gate at the jail’s Sally Port where prisoners are brought into the facility. Jail deputies were ordered to stand-down as they watched rioters destroy public property. None of the anarchists were arrested. One detention deputy at the jail told me, “It was ridiculous that we were not allowed to do anything, and no one was arrested, and it has deeply affected morale.”

Screenshot of Twitter video by @ByJoshSolomon.  Watch the video of the attempted jail break-in by clicking here.

7).  Apparently, Chronister’s cushy millionaire lifestyle (he lives in his wife’s million-dollar house in South Tampa) has spoiled him so much he needs a luxury vehicle to do his job. Chronister’s super-decked-out HCSO issued Chevrolet Tahoe exceeds what the agency normally buys, but Chronister’s bottom needs an easy ride – so he ordered the fancier vehicle and wrote the county a check for the difference of $18,000. While this doesn’t squeeze taxpayers directly, it certainly speaks to his character that he thinks he deserves a better ride than his deputies; and since he married-well and can afford to pay the difference over a stock vehicle and a fully loaded one, it’s okay. Talk about an unnecessary morale deflater.

8).  Despite having demonstrated he is good at squandering taxpayer dollars, Chronister avows to be a good steward of your money by claiming to have saved the county $15 million. But upon careful review, it is clear the savings are coming at the safety of the public with 170 deputy positions currently open and unfilled – which Chronister’s wasteful TV ad suggests he is trying to fix, but you can’t claim savings for something that you would rather be spending on, can you?

In short, Chad Chronister is an opportunistic and narcissistic politician who is woefully inadequate as Hillsborough County’s sheriff, and the citizens of the county deserve better.

Sheriff Chronister did not respond to my request for comment for this column.

Chris Ingram is a Tampa communications, political, and media consultant. Follow him on Twitter at @IrreverentView or send him an e-mail to


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