Janelle Irwin Taylor
Can you even be considered all that powerful these days if you haven’t earned President Donald Trump’s support AND ticked him off in the process?
That’s kind of what happened to Hillsborough County Sheriff Chad Chronister, who narrowly missed repeating this year as Tampa Bay’s Most Powerful Politician, instead landing this year just outside the No. 1 spot as the No. 2.
In December, Trump tapped Chronister to lead the Drug Enforcement Administration (DEA), noting that Chronister would work directly with Attorney General Pam Bondi “to secure the Border, stop the flow of Fentanyl and other Illegal Drugs across the Southern Border, and SAVE LIVES.” At the time, Chronister said the appointment was “the honor of a lifetime.”
Fast forward a couple of days, and Chronister was bowing out of Trump’s nomination. He maintained that the nomination was an honor, but claimed “the gravity of this very important responsibility set in” and he chose instead to continue his work for the citizens of Hillsborough County.
But the saga wasn’t done. The next day, Trump chimed in, saying it was not Chronister who bowed out, but Trump himself who withdrew the nomination. Trump said he “did not like what he said to my pastors and other supporters,” a likely reference to criticism Chronister faced from conservatives regarding his handling of the COVID-19 pandemic.
During the early stages of the pandemic Chronister, often seen as a moderating voice in conservative politics in Hillsborough County, announced the arrest of Dr. Rodney Howard-Browne, pastor of The River at Tampa Bay Church, for conducting a service during the height of social distancing policies. The charges ultimately were dropped, but it didn’t stop some Republicans from viewing the issue as disqualifying, including U.S. Reps. Thomas Massie of Kentucky and Chip Roy of Texas.
Still, Chronister maintained his version of events.
But it’s no secret that Chronister, a Republican, is willing to cross party lines. Last month, Chronister was one of several hosts at a luncheon for former Mayor Bob Buckhorn as he laid the foundation for a return to office.
His ability to work across the aisle, while seen now by some as a political liability in the age of Trump, has been one of the abilities that consistently keeps Chronister at the top of Florida Politics’ power list. Paired with Chronister’s fundraising prowess and his fearless politicking, there’s little doubt he’ll stay there.
“Hillsborough County is privileged to have Sheriff Chad Chronister at the helm, someone who we whole wholeheartedly believe to be the best Sheriff in Florida. He is unwavering in his commitment to the safety of our community and works tirelessly to pursue justice on behalf of the County’s residents,” said Jeff Johnston of Johnston & Stewart Government Strategies. “Not only that, but he is the definition of a class act, and one of the most kind and generous people you will ever meet. We could not be more honored to represent the Hillsborough County Sheriff’s Office, and to have the opportunity to advocate for Sheriff Chronister’s incredible team.”
Chronister’s rise has been almost meteoric, landing first on this list near the bottom, at No. 23, but climbing steadily since: to No. 16, then No. 9 and No. 7, before cracking the Top 5 in 2023.
The Hillsborough Sheriff announced his re-election campaign in early 2024, then promptly raised nearly $2 million in less than three months afterward. He didn’t even need the money — he was re-elected last year without opposition after his sole challenger, Gary Pruitt, failed to qualify for the race.
Chronister had faced Pruitt before, defeating him in 2018 with nearly 55% of the vote and again in 2020, in addition to topping a no-party candidate, Ron McMullen.
Chronister was first appointed in 2017 by then-Gov. Rick Scott.
His prominence in Tampa Bay area politics also comes because of — or to some, despite — bold moves Chronister has taken to protect public safety.
Worrying that criminals were not being prosecuted for their crimes, Chronister supported Gov. Ron DeSantis’ removal of former Hillsborough State Attorney Andrew Warren. Some saw it as a surprising move by Chronister, who is known for defying partisanship, reaching across the aisle and building meaningful relationships that transcend party loyalty. Agree with him or not, Chronister’s decision in that case was based not on politics, but on his commitment to public safety.
And his brand of leadership is paying dividends. Crime in Hillsborough is down 15%, as of 2024, inmates at the county jail have access to the largest mental health facility in the state and Chronister recently launched a new program training inmates for jobs — vocational or those that require college-level classes — after they’ve completed their sentences. It’s a strategy that aids in reducing recidivism.
In late 2024, Chronister launched Operation Safe Passage, a new initiative aimed at preventing speeding in school zones and keeping kids safe by utilizing camera technology. The program was possible through state legislation creating a regulatory framework for camera operators, similar to red light cameras.
It has been controversial, prompting new legislation this year that establishes a more effective appeals process and more appropriately assigns citation authority. Even though kinks are being worked out, Chronister, along with the Hillsborough County Commission and camera vendor RedSpeed, saw it as a way to increase student safety.
“Getting our children to and from school safely is a top priority for me as Sheriff of Hillsborough County,” Chronister said at the time. “Operation Safe Passage allows us to address dangerous driving in school zones while maintaining a consistent presence throughout our community.”
Without term limits in Hillsborough constitutional offices, Chronister’s time in office could carry on indefinitely, especially considering his success at the ballot box. What will be interesting to watch in the future is how Chronister’s pragmatic approach to collegial governance continues to fit in a reddening county. He won’t be on the ballot in the next election cycle, in 2026, but will be in 2028, leaving next year’s election as a possible bellwether for Chronister’s next re-election campaign.
“While the Tampa Bay region is beyond fortunate to be home to some of the Sunshine State’s most powerful politicians, it’s our leaders in law enforcement who continue to keep our communities safe. Sheriff Chronister is the first to show up to the scene of a crime, celebrations for some of Tampa’s most inspiring charities and even first and last days of school to greet Hillsborough students offering a comforting hug, a smile for a selfie or a high-five to cheer on our greatest treasures — Tampa’s youth,” said Ashley Bauman of Mercury Public Affairs.
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A special thanks to RSA Consulting Group, the sponsor of this year’s rankings.
As for methodology, we define the Tampa Bay region as Pinellas, Hillsborough and Pasco, but we can also include Hernando, Polk or Sarasota if the politicians from those counties impact either Pinellas or Hillsborough.
We define a politician as being in office or running for office.
Being first on a panelist’s list earns the politician 25 points, second earns them 24 points, and so on, to where being listed 25th earns a politician one point. Points are added and, voilà, we have a list.
We also want to thank our experienced and knowledgeable panelists, who were essential to developing the 2025 list: Vinik Family Office Chief of Staff Christina Barker; Mercury Public Affairs Managing Director Ashley Bauman; Matt Blair of Corcoran Partners; Reggie Cardozo of The Public Square; Stephanie Cardozo of The Southern Group; Shumaker, Loop & Kendrick managing partner Ron Christaldi; former state Sen. Janet Cruz; political consultant/strategist Barry Edwards; Vicidial Group President Matt Florell; Sunrise Consulting Group President Shawn Foster; businessman Michael Griffin; Clay Hollis of Tucker/Hall; Natalie King of RSA Consulting Group; Moffitt Cancer Center VP of Public Affairs and Communications Merritt Martin; former state Rep. Seth McKeel of The Southern Group; political consultant Chris Mitchell; Mike Moore of The Southern Group; RSA President and CEO Ron Pierce; Tucker/Hall CEO Darren Richards; political consultant Jim Rimes; political consultant Preston Rudie of Catalyst Communications Group; TECO VP of State and Regional Affairs Stephanie Smith; lobbyist Alan Suskey of Shumaker Advisors; Doyle Walsh, Chief of Staff for St. Pete Mayor Ken Welch; and Michelle and Peter Schorsch, publishers of Florida Politics.
