Hillsborough sheriff’s political past became liability after Trump’s DEA nomination

TAMPA — For a moment last week, it seemed Chad Chronister had arrived.

Tapped by President-elect Donald Trump to lead the Drug Enforcement Administration, the Hillsborough County sheriff stood at the pinnacle of a career that has seen him ascend from humble beginnings to one of Tampa Bay’s preeminent power brokers. He called his selection to lead the federal agency “the honor of a lifetime.”

Barely three days later, he withdrew. In a statement, the sheriff said the “gravity of this very important responsibility” led him to conclude that he had to bow out from consideration.

He’s offered no other specifics, and his office said he wasn’t available for interviews. But his withdrawal came amid criticism from some on the political right about Chronister’s record. The sheriff’s 2020 arrest of a church pastor accused of violating COVID restrictions became a particular sticking point for some national conservatives, among whom Chronister wasn’t previously well known.

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The episode underscores the complicated political history of a sheriff who has called himself “the most Democratic of Republicans.” The progressive policy moves that have been an asset to him as the top cop in a once-purple county are liabilities in the world of Trump.

On Wednesday, Trump claimed on Truth Social, his social media platform, that he chose to yank Chronister’s nomination.

“He didn’t pull out, I pulled him out, because I did not like what he said to my pastors and other supporters,” Trump wrote.

Chronister didn’t directly respond to that assertion.

“Sheriff Chronister stands behind his decision to withdraw from consideration,” a spokesperson for his office said in a statement. “Right now, his priority, as it has been for the last seven years, remains the mission to protect and serve everyone in Hillsborough County.”

A forgiving pastor, an irked public

Within 24 hours of the news that Trump would nominate Chronister to lead the federal agency, the sheriff took a seat beside Rodney Howard-Browne, a conspiracy theorist who claimed the coronavirus was a socialist plot to take over the government and kill people with vaccines. He’s the pastor of the River at Tampa Bay Church, whom Chronister famously had arrested in 2020 for flouting COVID-19 lockdown restrictions by continuing to have in-person services at his church. The men spoke before a pair of microphones as a camera rolled.

Chronister, a gold badge and collar stars affixed to his white uniform, smiled as the pastor said they remained friends despite the arrest and that he supported his nomination.

“I have always appreciated that you know that I’m a follow-the-law sheriff, and I was following the law back then,” Chronister said. “And lousy laws, good laws, you have to be the sheriff and do your job, and you always understood that.”

The sheriff added that he was “proud that Florida was the first to roll back all those COVID restrictions.” He recalled it being a “happy day” when he phoned the state attorney to say that charges against the pastor should be dropped. He called the pastor a “true friend.”

The three-minute video, which Howard-Browne later shared on social media, contrasted with what Chronister said nearly five years ago. In a news conference where he announced the pastor’s arrest, the sheriff said Howard-Browne had acted with “reckless disregard” for public safety by ignoring repeated warnings to abide by quarantine orders.

“Shame on this pastor, their legal staff and the leaders of this staff for forcing us to do our job. That’s not what we wanted to do during a declared state of emergency,” Chronister said then. “We are hopeful that this will be a wake-up call.”

The arrest drew national attention and questions over the proper balance of public health and the free exercise of religion. Nevertheless, within weeks, the pastor and the sheriff broke bread together. Soon after, the criminal case dissolved.

Still, the episode became a flashpoint of criticism among some conservatives after Trump nominated Chronister. Conservative social media outlets prominently highlighted stories about Chronister’s handling of the pastor’s arrest. U.S. Rep. Thomas Massie, R-Kentucky, a Trump supporter, said the episode should disqualify Chronister from leading the DEA.

It didn’t appear to matter that the pastor himself said Chronister’s leadership made him an “ideal candidate.”

“Chad’s journey is a testament to resilience and growth,” Howard-Browne wrote in a statement. “He has turned challenges into learning experiences, proving that we are not defined by mistakes, but by how we rise above them.”

‘The most Democratic of Republicans’

A chorus of consternation from the MAGA-sphere also highlighted Chronister’s approach to immigration, gun violence and Black Lives Matter protests.

The criticism harked back to the sheriff’s early tenure when he crafted an image as a moderate Republican who viewed his job as nonpartisan.

“The right’s gone way too far right for me,” he told the Tampa Bay Times in 2019. He characterized himself as “the most Democratic of Republicans,” fiscally conservative and socially liberal.

He supported enhanced mental health screenings for gun purchases, a position decidedly out of step with the National Rifle Association. He voiced support for universal background checks and red flag laws, which allow courts to order guns taken from people deemed a threat to themselves or others.

In his first few years in office, Chronister worked with then-State Attorney Andrew Warren, a progressive Democrat, and other local leaders to create and expand juvenile civil citations. They helped launch adult pre-arrest diversion programs and a juvenile mental health court.

In 2020, he endorsed Warren’s reelection campaign, calling him a “partner” in criminal justice.

That year, Chronister faced allegations from his Republican primary challenger that he was soft on crime and a RINO, or “Republican in name only.” Still, he handily secured his own reelection victory against multiple opponents.

And in the weeks after, he was one of the few Republicans to publicly contradict Trump’s claims of a stolen presidential election.

“I believe that Biden has won the election,” Chronister said in late November. “I believe Trump should concede. I don’t think anyone has provided any evidence of any fraud.”

When Gov. Ron DeSantis twice held news conferences in 2020 and 2021 to promote what was dubbed the “anti-riot bill” — a response to violence that occurred after the murder of George Floyd at the hands of Minneapolis police — other sheriffs attended, but Chronister wasn’t invited. Chronister didn’t vocally oppose the bill, though his response to it was tepid.

He nevertheless stayed in the governor’s good graces. Chronister became a key player behind the scenes when DeSantis suspended Warren from office in 2022. He gave the governor a list of cases he said Warren had failed to prosecute. He accused Warren of “empowering criminals” and expressed frustration with prosecutorial decisions he made.

“The issue I’ve always had with State Attorney Warren is his lack of prosecution, his lack of fighting,” Chronister told the Times in 2022.

When DeSantis ran this year in the Republican presidential primaries, Chronister was among those who endorsed him over Trump. Chronister’s father-in-law, Eddie DeBartolo Jr., has hosted DeSantis, the sheriff and their families, among other Republicans, at his sprawling Montana ranch. Trump in 2020 pardoned DeBartolo, who had been convicted in a gambling fraud scandal.

At the same time, Chronister became an enthusiastic backer of Suzy Lopez, the longtime prosecutor appointed to replace Warren. He used his own political resources to help fund her ultimately successful campaign against the ousted state attorney.

His tone on criminal justice issues seemed to shift. A year after Warren’s removal, he noted a 500-person increase in the local jail population, saying it was “because we’re holding individuals accountable for the crimes that they committed, while still fixing people.”

Yet when Chronister and Warren happened to run into each other at an event last summer, they hugged.

Trump’s followers this month also noticed a video Chronister released in 2023 in response to a law passed by Florida’s Legislature designed to crack down on illegal immigration. Chronister praised the “rich diversity” of his community and called it “a place where people from all walks of life come together.”

He said it was important to note his office “does not engage in federal immigration enforcement activities. We do not target individuals based on their immigration status. That’s the authority of federal agencies.”

Trump has made a sweeping crackdown on immigration a central focus of his coming administration. The president-elect and many of his ardent backers have linked immigration policy under the Biden administration to the flow of drugs into the country.

Any displeasure with Chronister from within his own party didn’t materialize into a primary challenge this year. He was reelected without opposition to a second four-year term.

A mixed record

State Rep. Danny Alvarez, R-Valrico, who previously worked with Chronister as a high-level sheriff’s office civilian employee, said some faction of his and Chronister’s party “is begging for Republican perfection.”

”There’s no way you’re going to accomplish that when you’re supposed to be a neutral bringer of justice,” Alvarez said. “You’re never going to make everyone happy. Overall, is Hillsborough County safer and better? I would argue with anyone, any day, on behalf of Chad Chronister that it is.”

Ione Townsend, who has been chairperson of the Hillsborough County Democratic Executive Committee for nine years, said Chronister’s record has been a “mixed bag.” While praising his criminal justice reform efforts, Townsend said his involvement in Warren’s suspension was a disappointment. The episode made her and others wonder if the sheriff was maneuvering for a higher office.

“So when this DEA thing happened, we said, you know, it’s coming to fruition,” Townsend said.

Some also questioned whether Chronister’s skills would translate at the federal level.

Although the Hillsborough County Sheriff’s Office is among the largest local law enforcement agencies in the country, Chronister would have been leading a much bigger operation. The DEA employs nearly 10,000 people and has 334 offices, 91 of them in 60 foreign countries, according to its website. Its budget this year is about $3.3 billion.

By comparison, the sheriff’s office has about 3,600 employees and a budget this year of about $600 million.

Chronister mentioned his hopes for the new role when he appeared in the video with Howard-Browne.

”I told President Trump,” Chronister said, “on day one, we’re going to knock on the cartels’ doors, we’re going to knock on the Venezuelan gang doors, these organizations that are distributing this poison that’s killing our loved ones, and I’m going to deliver a loud message on his behalf that this stops today.”

Though county sheriffs tend to be well versed in domestic law enforcement, Chronister would have to get up to speed on the international side of the agency, said Brian Boyd, a former senior DEA intelligence analyst. Tackling the flow of fentanyl into the country, which Trump said should be a top priority, is an international endeavor.

“A lot of the agents are stationed in embassies,” Boyd said. “So he’d have to have a whole lot of exotic clearances provided to him in order to be able to understand the heavy diplomacy and the difficulties of working with agents overseas.”

Yvette Lewis, president of the Hillsborough County branch of the NAACP, said she has found Chronister to be proactive and responsive as sheriff. She praised his efforts to create diversion programs for low-level offenders and launch educational and vocational programs in the county jail, as well as his openness amid the unrest that followed the murder of George Floyd in 2020.

Lewis said she was “completely shocked” when she heard Chronister was willing to work in the Trump administration.

“I don’t see him as a MAGA person at all,” Lewis said. “What I do see is a person who is progressive on how to honestly, really make things better again.”

His approach is not the same as that of Trump and the MAGA movement, Lewis said.

“His heart is not like theirs,” she said. “I think he would have been miserable.”

Information from The Associated Press was used in this report.

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