The way they met is reminiscent of the plot of a Hallmark Channel movie.
She was the daughter of Eddie DeBartolo Jr., former owner of the San Francisco 49ers and granddaughter of the man who introduced the mall concept in the 1950s. He was a local sheriff’s deputy who had worked as a hotel doorman, digging ditches and unloading UPS trucks at night before joining the police force — and getting hired as a security guard for her family in Tampa.
“He was always there,” said Nikki DeBartolo, 49. “Even when he wasn’t working, he was there.”
Nikki DeBartolo and Chad Chronister, sheriff of Hillsborough County since 2017, have a 14-year marriage that makes him the most unusual of the many other sheriffs in Florida’s 67 counties.
He’s a man with a foot in two worlds: at the scene of a shooting in rural Ruskin one day, on a private jet to go fishing with his son in the Keys the next. He’s at the Super Bowl, the Espys. He’s dating football great Joe Montana. Boyz II Men, friends of the family, played to more than 200 guests at their Palm Beach wedding and later in his first campaign.
“It took some getting used to,” says Chronister, 56. “I remember eating tuna and ramen noodles when I was in school.”
The DeBartolos arrived in Tampa in 2000 at a difficult time for the family: Eddie DeBartolo Jr., whose team won five Super Bowls during his tenure, pleaded guilty in 1998 to a felony charge of failing to report that he had been extorted by former Louisiana Gov. Edwin W. Edwards over a gambling license for a riverboat casino. DeBartolo agreed to testify against Edwards, who eventually went to federal prison. With it all came death threats for the family, Chronister said.
DeBartolo set up his business in Tampa, the connection partly being former Mayor Dick Greco, who had worked for DeBartolo’s father. Chronister was hired for an additional job as part of a security team.
They went shopping, “we went shopping,” Chronister said.
He would later call meeting Nikki DeBartolo love at first sight. But for years they were friends.
Both had been married before. Eventually there was a kiss, then a break while she sorted things out, he said. She called him in late 2008 and they met in a shopping mall parking lot and talked for hours.
The DeBartolos had long treated him as one of their own — “my parents loved him,” she said — but marrying a daughter was a new problem, Chronister said. “It took us a while to make the transition,” he said. “You’re sitting at the employee table and all of a sudden you’re sitting at the family table.” He convinced her 6-year-old son, Asher, to propose.
When Sheriff David Gee unexpectedly retired in 2017, Chronister was appointed as his replacement on Gee’s recommendation.
Chronister made a successful bid for the position in 2018 and was re-elected unopposed this year.
A major political moment in Florida was also a moment in their marriage.
In 2022, Chronister found himself in the middle of a battle between Republican Gov. Ron DeSantis and Hillsborough State Attorney Andrew Warren, a progressive Democrat. The sheriff and state attorney had called each other friends, but Chronister said he took issue with Warren’s prosecutorial decisions and policy against pursuing specific nonviolent misdemeanor cases.
When the governor announced Warren’s surprise suspension, Chronister and other sheriffs stood next to him during the press conference.
Chronister heard the governor say in front of the cameras that the suspension was also due to pledges Warren had signed with prosecutors across the country not to prosecute cases involving transgender health care or abortion — two major and contentious national issues.
“I didn’t know it had anything to do with anything other than not prosecuting petty crimes until (DeSantis) said so,” Chronister said. As soon as it was over, he called his wife, who he knew had opinions on both subjects.
She said she could tell from the look on his face at the press conference that it was a surprise to him.
“I know him,” she said.
She works with the DeBartolo Family Foundation, which has donated millions over the years to charities including veterans, children and the Humane Society. The couple can be seen together at fundraisers, galas and work-related speeches and events.
“I never take this for granted,” Chronister said. “I know how lucky I am.”
According to state financial disclosure forms, his net worth was $24 million in 2024.
That they are a powerful couple has led to speculation about their political future, and not just him.
About the rumor that he wants to run for mayor when Jane Castor’s second term is up? No, he said, although he will likely run again.
“I love being sheriff,” he said. “When people say I’m done being sheriff, I’m done. I have no aspirations of being anything else.”
That doesn’t stop the discussion: “I shudder every time someone says, ‘Your husband should run for governor,'” DeBartolo said. “We’re happy.”
And anyone wondering about her political future clearly doesn’t know that she’s afraid of public speaking, she said.
“I love going to charity events and making a difference,” she said. “But no. I love being by his side.”
