TAMPA — In 1964, the Beatles appeared on the Ed Sullivan Show, the first Ford Mustang rolled into showrooms and Mary Poppins hit movie theaters.

It was also the last time Hillsborough County saw a truly competitive race for sheriff.

In a tradition that has endured here and at other agencies throughout the state, a longtime sheriff steps aside and throws his support behind a subordinate, who then gets endorsed by the local political establishment.

To some, that means a tough job goes to a seasoned, tested candidate. Others contend it's more like a regal line of succession that can marginalize voters and shut out qualified candidates from outside the agency. A parade of like-minded successors, they say, can march an office into stagnation.

Into this political landscape steps Chad Chronister, 50, who was handpicked by former Sheriff David Gee. During 26 years on the Hillsborough force, Chronister has worked the midnight patrol shift, bought drugs and guns as an undercover detective and barged into unknown danger with the SWAT team.

Sheriff Chad Chronister, left, congratulates his patron, former Sheriff David Gee, as Gee receives a good government award in April from the Hillsborough County Commission. Gee’s wife Rhonda is at center. [CHRIS URSO | Times]
Sheriff Chad Chronister, left, congratulates his patron, former Sheriff David Gee, as Gee receives a good government award in April from the Hillsborough County Commission. Gee’s wife Rhonda is at center. [CHRIS URSO | Times]

The telegenic Chronister is a fixture on social media, a Republican with prominent local bipartisan support and, thanks to his marriage into the DeBartolo family of NFL and real estate fame, has amassed a war chest larger than anyone who has ever run for local office in Hillsborough.

Is he the right man at the right time? Or the heir to an exclusive tradition?

"I understand the culture of the office, the needs of the employees and the needs of the community," Chronister said, "so I have a huge advantage because I think those are the three most important things."

• • •

The timing of Gee's early retirement last year — less than a year into his fourth four-year term — raised questions about whether he was setting up Chronister to run as an incumbent. Gee dismissed that theory, telling the Tampa Bay Times last June it wasn't any one thing that prompted him to step aside so early, but "a little bit of everything."

Gee did not return messages requesting an interview for this story. Instead, through Chronister, he referred the Times to the two-page letter he sent to Gov. Rick Scott recommending Chronister's appointment.

Sheriff Chad Chronister, at an April County Commission meeting, acknowledges he has been given a leg up in the campaign for sheriff, but frames it as a chance for voters to see him in action. [CHRIS URSO | Times]
Sheriff Chad Chronister, at an April County Commission meeting, acknowledges he has been given a leg up in the campaign for sheriff, but frames it as a chance for voters to see him in action. [CHRIS URSO | Times]

Gee wrote, "As Sheriff, the stakes are always high: missteps resulting from inexperience or other shortcomings can threaten the confidence employees and citizens have in their sheriff."

A colonel in the office at the time, Chronister follows his own personal philosophy in his work, Gee wrote: "You listen and you learn, and then you lead."

Hillsborough Democrat Alex Sink, who narrowly lost to Scott in the 2010 gubernatorial race, is a Chronister supporter and acknowledges that Gee's early departure "feels engineered." But like others, Sink takes Gee's word that political maneuvering was not a factor in his decision to step aside.

"I don't think he's got a manipulative bone in his body."

Former Hillsborough State Attorney Mark Ober, who calls Gee a friend, said outside candidates rarely have the right qualifications.

"This is a massive agency," Ober said. "The internal workings of the Sheriff's Office are very technical."

There's another incentive for top department officials to help an insider win. The sheriff appoints majors and colonels, removing them from civil service protection. Outsiders are more likely to clean house.

It's nearly impossible for an outsider to win the sheriff's title in Hillsborough, said Darryl Paulson, professor emeritus of government at the University of South Florida St. Petersburg. For one thing, running a countywide race is expensive.

"It's larger than a congressional district, so you have to reach far more people and raise a substantial amount of money to be competitive," Paulson said.

Sheriff Chad Chronister named Donna Lusczynski as his chief deputy in May. In a sheriffs line of succession lacking in diversity through the years, Lusczynski becomes the office’s highest-ranking woman ever. At right is her brother Lawrence Weindorf. [OCTAVIO JONES | Times]
Sheriff Chad Chronister named Donna Lusczynski as his chief deputy in May. In a sheriffs line of succession lacking in diversity through the years, Lusczynski becomes the office’s highest-ranking woman ever. At right is her brother Lawrence Weindorf. [OCTAVIO JONES | Times]

The two men who filed to challenge Chronister — former Tampa Police Cpl. Gary Pruitt, a Democrat, and retired Central Intelligence Agency officer Juan Rivera, a no-party candidate — say the entrenched system of succession spurred them to assume the role of electoral Davids to Chronister's Goliath.

Rivera dropped out last month after raising only $722. He called the system rigged. Pruitt, who has pledged to do away with what he called "the good old boy system," has raised just $3,310.

The system has yet to produce a female or minority sheriff, though Chronister recently promoted Col. Donna Lusczynski to serve as his chief deputy.

Mayor Bob Bob Buckhorn, center, has known Sheriff Chad Chronister, left, about eight years and sees his ascension as part of a process that works. The two men attended a neighborhood meeting in January after an arrest in the Seminole Heights slayings, a gathering also attended by Aretha Jones of Tampa, right, mother of a victim in the slayings, and Tampa Police Chief Brian Dugan. [ALESSANDRA DA PRA | Times]
Mayor Bob Bob Buckhorn, center, has known Sheriff Chad Chronister, left, about eight years and sees his ascension as part of a process that works. The two men attended a neighborhood meeting in January after an arrest in the Seminole Heights slayings, a gathering also attended by Aretha Jones of Tampa, right, mother of a victim in the slayings, and Tampa Police Chief Brian Dugan. [ALESSANDRA DA PRA | Times]

Tampa Mayor Bob Buckhorn, another prominent Democrat supporting Chronister, said he has watched the local succession process shape sheriffs with different styles, strengths and weaknesses, but "each of them right for the time." A contested election, Buckhorn said, wouldn't have changed that.

Buckhorn has known Chronister about eight years and sees him as the product of a process that works.

"I think he's the right guy for the job," he said. "It's his moment."

• • •

Chad Gregory Chronister was born and raised in York, a blue-collar town of about 43,000 people in the rolling hills of southeastern Pennsylvania. His father, Danny, was a postal worker, then got into the restaurant and lounge business. His mother, Helena Bentivegna, said she realized quickly that the marriage was a mistake, but the couple stayed together for their son and daughter Lisa, born a year after Chad. They eventually divorced.

"My life was with the kids. His life was out working."

Chronister recalls his father working at night, sleeping much of the day and drinking heavily.

"I saw my father as something I didn't want to ever be."

Grandfather Jack “Nanu” Bentivegna, a Marine veteran, stepped into the role of father figure for a young Chad Chronister while Chronister was growing up in York, Pa. They visited here on the day of Chronister’s high school prom. Bentivegna died in 2013, the year Chronister was promoted to captain at the Sheriff’s Office. [Courtesy Helena Bentivegna]
Grandfather Jack “Nanu” Bentivegna, a Marine veteran, stepped into the role of father figure for a young Chad Chronister while Chronister was growing up in York, Pa. They visited here on the day of Chronister’s high school prom. Bentivegna died in 2013, the year Chronister was promoted to captain at the Sheriff’s Office. [Courtesy Helena Bentivegna]

Danny Chronister acknowledges his failings during a period in his life when he worked 70-hour weeks and drank too much. He said he later worked to reconnect with his teenage son and eventually helped Chad buy a condo in Florida.

"There were a lot of good years and good things we did together," said Danny Chronister, now a pastor in North Port.

Father and son don't speak often. Danny Chronister said he thinks he learned of his son's appointment to sheriff through a news report, then donated $100 to his campaign.

Chad Chronister said he never lacked for a father figure. His grandfather, Jack Bentivegna, a U.S. Marine veteran who saw combat in World War II, lived on the next street.

Chronister got "decent" grades in school, he said. He played junior varsity football, ran track and dabbled in theater production. His father in mind, he steered clear of drugs and alcohol. He recalls other teens laughing when he showed up to parties toting apple juice.

Chronister was a skinny, well-liked "late bloomer" who easily transcended cliques, said lifelong friend John Snyder.

"He could sell ice to Eskimos," Snyder said.

Chronister graduated from high school in 1986 and enrolled at Mansfield University, a small state school, where he studied business and communications.

During one spring break, he came to Tampa to visit a great uncle and fell in love with the area. He looked up to his grandfather, but also felt overwhelmed by him and the Bentivegna family's outsized presence in York. Tampa was a place beyond the man's shadow, where the weather was nice enough to water ski all year.

After two years at Mansfield, Chronister packed up and headed south.
Three years later, he was scraping by as a plumber's assistant and package sorter for UPS when he sat down to fill out a Sheriff's Office job application.

• • •

Chronister started at the Sheriff's Office academy on Valentine's Day 1992, two weeks after marrying his then-girlfriend, Teresa Card. That June, he became a full-time patrol deputy.

In his first performance evaluation, Chronister was described as an eager-to-learn "self-starter" whose investigative skills helped put him among the leaders in his squad for arrests.

Over the next decade, Chronister would be promoted to detective and work in a variety of assignments.

A baby-faced Chad Chronister and his then-partner Miguel Diaz show off a kilo of cocaine seized during a bust in 1997, when the two men were narcotics detectives. Chronister has worked in nearly every part of the Sheriff’s Office and his quick rise earned him the nickname “golden boy.” [Twitter]
A baby-faced Chad Chronister and his then-partner Miguel Diaz show off a kilo of cocaine seized during a bust in 1997, when the two men were narcotics detectives. Chronister has worked in nearly every part of the Sheriff’s Office and his quick rise earned him the nickname “golden boy.” [Twitter]

Former partner and friend Thomas St. John, now a sheriff's lieutenant, said Chronister always treated people fairly and with dignity.

"There were bad guys that we'd arrest who, before the night was over, would apologize to him for him having to arrest them," St. John recalled.
In January 1997, Chronister fired his service weapon in the line of duty for the first time and only time — with deadly results.

It happened while he and St. John were working an undercover drug bust in north Tampa. A man, later identified as a U.S. Navy veteran with mental health issues, came upon two other undercover deputies, grabbed a handgun from one and tried to shoot them. When Chronister and St. John arrived, the man pointed the gun at them. Both fired, killing him. An investigation concluded the shooting was justified.

Chronister's relatively brief time on patrol and rapid movement among plum assignments earned him the nickname "golden boy" among some coworkers.

His personal life, however, had a series of highs and lows.

He and Teresa celebrated the birth of their son, George Zachary, in 1993. But Chronister moved out less than a year later and in 1995, Teresa filed for divorce, citing irreconcilable differences, court records show.

"Unfortunately, I had no business being married," Chronister said.

Their son, who goes by Zack, lived with his mother. Chronister had visitation but said he struggled to get time with the boy.

In 1997, Chronister married Tammy Edwards. They divorced two years later but dated on and off for a while before parting for good. Edwards declined an interview request, but offered an assessment of her ex-husband's career: "I think he's been given a lot of opportunities and he has taken the ball and run with it and not disappointed anyone who's given him the opportunity."

The relationship that led to his third marriage started in 2000 when Chronister, a detective, volunteered for an extra-duty assignment.

Eddie DeBartolo Jr., who won a record five Super Bowls as owner of the NFL's San Francisco 49ers, reached out to the Sheriff's Office for security for his family, including wife, Candy, and daughters Nikki and Lisa. The DeBartolos lived among the mansions in Tampa's Avila Golf and Country Club.

Deputies in the detail assembled one day to meet with the family. Chronister called it love at first sight when Nikki walked in.

"I was just like, 'Wow.' "

• • •

Chronister came into the DeBartolos' lives at a difficult time for the family. Two years earlier, DeBartolo had pleaded guilty in a sprawling probe of Louisiana's gambling industry and surrendered his ownership of the 49ers.

DeBartolo Entertainment had partnered with another company to submit a bid for a riverboat casino license, and FBI surveillance records showed that Eddie DeBartolo sought information and influence from former Louisiana Gov. Edwin Edwards.

Sheriff Chad Chronister and his wife Nikki DeBartolo part company after a hospital visit in April with a boy who was the victim of a crime. Their marriage eight years ago was the third for Chronister, the second for DeBartolo. [CHRIS URSO | Times]
Sheriff Chad Chronister and his wife Nikki DeBartolo part company after a hospital visit in April with a boy who was the victim of a crime. Their marriage eight years ago was the third for Chronister, the second for DeBartolo. [CHRIS URSO | Times]

DeBartolo later pleaded guilty to a felony — failing to report Edwards had extorted money from him to help secure the gambling license. DeBartolo agreed to pay $1 million in penalties and serve two years probation in exchange for testifying against Edwards and his son.

Jim Letten, the lead prosecutor on the case and now a private attorney, called DeBartolo a good man faced with a terrible choice.

"By acceding to this demand, he violated the law and we had to hold him accountable," Letten told the Times.

Lured in part by Tampa Mayor Dick Greco, who had worked for DeBartolo's father, Eddie DeBartolo Jr. moved to Florida in 1998. He made Tampa the headquarters of a holding company with interests including real estate development, sports management and restaurant franchising.

Chronister and Nikki DeBartolo said the family hired the sheriff's detail because they were getting death threats in the wake of the Edwards case.
"It was a scary time for our family," Nikki DeBartolo recalled.

Eddie DeBartolo remembers the circumstances differently, telling the Times he brought security on as a precaution, not because of death threats.
He recalls thinking Chronister was trustworthy and honorable, "just like he is now."

By the time the detail ended, Chronister was friends with Nikki and the rest of the family. He was waiting at the hospital when Nikki gave birth to her son, Asher.

Nikki DeBartolo was married at the time to Benjamin Heldfond, member of a wealthy California family and now the owner of an investment firm. They divorced in 2008. Shortly after that, at the end of a friendly outing, Chronister and DeBartolo shared their first kiss, but she told Chronister she wasn't ready for a relationship.

Nikki DeBartolo and Chad Chronister, center, were married in 2010 at the Ritz-Carlton Palm Beach in front of more than 200 guests. Boyz II Men, friends of the family, played at the reception. Also pictured are DeBartolo’s son Asher, at center foreground, and Chronister’s son Zack, far right. [Courtesy of Nikki DeBartolo]
Nikki DeBartolo and Chad Chronister, center, were married in 2010 at the Ritz-Carlton Palm Beach in front of more than 200 guests. Boyz II Men, friends of the family, played at the reception. Also pictured are DeBartolo’s son Asher, at center foreground, and Chronister’s son Zack, far right. [Courtesy of Nikki DeBartolo]

Then, in December 2008, she called him. They met in a shopping center parking lot and acknowledged how much they wanted to be together. Just months later, Chronister slipped a nearly 6-karat ring on her finger after enlisting Asher to pop the question for him.

"I saw this woman who just had a huge heart who couldn't do enough for anyone," Chronister said.

Nikki, 42, calls Chronister "one of the most lovable and caring men I've ever met."

"I knew he would love Asher as much as I do," she said. "To me, that's the most important thing."

They married in 2010 at the Ritz-Carlton Palm Beach in front of more than 200 guests. Boyz II Men, friends of the family, played at the reception.

• • •

The DeBartolos and their associates have fueled Chronister's steamroller of a political campaign, donating a total of at least $148,000 to a candidate fund and to a separate political action committee that now total more than $1 million.

Chronister has also developed ties with DeBartolo business interests. Along with his Sheriff's Office salary of $183,589, Chronister listed $55,000 in primary income from DeBartolo Holdings LLC in 2017, according to a financial disclosure form submitted to the Hillsborough County Supervisor of Elections Office. Nikki Chronister is a vice president of DeBartolo Holdings.

NFL great Ronnie Lott, left, who played 10 years with the San Francisco 49ers, enjoys a moment with former team owner Eddie DeBartolo Jr. during the annual All Star Charity Gala in Tampa. The charity event is sponsored by the DeBartolo Family Foundation. The DeBartolos and their associates have contributed at least $148,000 toward the election of Sheriff Chad Chronister. [AMY SCHERZER | Times (2016)]
NFL great Ronnie Lott, left, who played 10 years with the San Francisco 49ers, enjoys a moment with former team owner Eddie DeBartolo Jr. during the annual All Star Charity Gala in Tampa. The charity event is sponsored by the DeBartolo Family Foundation. The DeBartolos and their associates have contributed at least $148,000 toward the election of Sheriff Chad Chronister. [AMY SCHERZER | Times (2016)]

Chronister and a trust in Nikki DeBartolo's name are the registered agents of an investment company, DeChron Holdings LLC, valued at more than $3.3 million in 2017, the financial disclosure shows. Chronister received income from Odessa car dealership Any Car USA, Black Rock Bar & Grill in Tampa, and a Tampa company that owns PDQ restaurants, according to the disclosure.

He listed his net worth last year at more than $4.3 million.

Nikki DeBartolo also helps run the DeBartolo Family Foundation, which holds a star-studded annual gala in Tampa and has given away, by her father's accounting, more than $14 million.

Chronister and the DeBartolos said he has never had a hand in the day-to-day operations of the family's companies and they said they can't envision conflicts with his job as sheriff.

Eddie DeBartolo said his company's interests are mostly outside Hillsborough. DeBartolo landed at No. 277 on last year's Forbes list of the 400 wealthiest Americans with an estimated net worth of $2.7 billion.

Chronister lives with Nikki and Asher in a bayfront Mediterranean-style mansion in South Tampa. The Hillsborough County Property Appraiser puts the value of the roughly 8,000-square-foot home at nearly $4.8 million.

Bentivegna, Chronister's mother, said her son successfully navigates "two different worlds."

"I call the DeBartolos the la la land, because how many people have that kind of money and that lifestyle?" she said.

Sheriff Chad Chronister stays connected by phone during a security meeting in April at Raymond James Stadium. Chronister said he gets invited to a lot of events and tries not to say no. He sees introducing himself and using social media to share what he’s doing as a “vital part” of his job. [CHRIS URSO | Times]
Sheriff Chad Chronister stays connected by phone during a security meeting in April at Raymond James Stadium. Chronister said he gets invited to a lot of events and tries not to say no. He sees introducing himself and using social media to share what he’s doing as a “vital part” of his job. [CHRIS URSO | Times]

One of Chronister's closest friends, Hillsborough sheriff's Detective Eric Giallanza, said wealth hasn't changed Chronister. It's nice to have a boat to take Asher fishing, a home theater to watch movies with the family, a personal gym.

"But I think Chad would be just as happy, because I knew he was just as happy, without any of that," Giallanza said. "He has a purpose to get up every day."

The lifestyle took some getting used to, Chronister said, but it helped to see that the DeBartolos manage their wealth with compassion.

"I've never met a more down-to-earth family," he said.

Chronister calls Asher "one of my biggest blessings in life.

"I think he's taught me how to be a father," he said, his voice catching. "How to love a human unconditionally."

The boy, 14, has given Chronister a second chance at hands-on parenting.

Zack Chronister, now 24, lives with his mother and is awaiting trial on an aggravated battery charge. An amateur rapper who goes by the name "Zchronik," he says he acted in self defense when he slashed another man in the face with a knife in February 2017.

Zack Chronister's attorney, Ronald Darrigo, declined to make mother or son available for an interview.

• • •

As he campaigns, now eight months into the job, Chronister is making the most of his title as sheriff.

He has inscribed his name on Sheriff's Office materials and inventory from business cards to the Marine Unit's 40-foot powerboat. He is one of just 10 or so among Florida's 66 sheriffs who position their faces rather than office seals on social media accounts.

From business cards to the Marine Unit’s 40-foot power boat, Sheriff Chronister’s name has been added to the office’s materials and inventory during his eight months on the job. [Twitter]
From business cards to the Marine Unit’s 40-foot power boat, Sheriff Chronister’s name has been added to the office’s materials and inventory during his eight months on the job. [Twitter]

Chronister's schedule is packed with appearances, photographed and posted day after day for the agency's more than 92,000 Facebook, Instagram and Twitter followers. The latest photos of him — often in his sheriff's white shirt, gold badge and collar stars — also go out via a Twitter account maintained in his name.

Chronister said he gets invited to a lot of events as sheriff and tries not to say no. He sees introducing himself to the community and using social media to share what he's doing as a "vital part" of his job.

He acknowledges he has been given a leg up in the campaign for sheriff, but frames it as a chance for voters to see him in action.

Since taking the helm, Chronister, who holds a master's degree in criminology from St. Leo University, has expanded a juvenile citation program that Gee was slow to support. He also worked with Public Defender Julianne Holt and Hillsborough State Attorney Andrew Warren — both prominent Democrats who have endorsed him — to launch a diversion program for adult first-time offenders.

Within the office, he's reshaping the command staff, has modified eligibility requirements to address a deputy shortage and is ramping up a partnership with the Boys & Girls Clubs to open more community centers.

Voters, he said, can assess the job he's done.

"I believe I'll have a track record."

Times senior news researcher John Martin contributed to this report.

No contest: Hillsborough County sheriff’s races

Hillsborough County hasn't seen a truly competitive race for sheriff since 1964. Here's an election-by-election rundown since then.

1964: Incumbent Sheriff Ed Blackburn loses to fellow Democrat Malcolm Beard in a tight, bitterly contested race.

Robert Ed Blackburn Jr., former Hillsborough sheriff and state lawmaker. [Times files (1992)]
Robert Ed Blackburn Jr., former Hillsborough sheriff and state lawmaker. [Times files (1992)]

1968: Beard wins without opposition.

1972: Beard wins a primary landslide against a Democratic write-in candidate, retired Tampa police Capt. Charles Renfroe, and faced no Republican opposition.

Malcolm Beard won the last truly contested race for Hillsborough sheriff [Times files (1971)]
Malcolm Beard won the last truly contested race for Hillsborough sheriff [Times files (1971)]

1976: Beard handily defeats Republican opponent Al Ford, a retired Tampa police lieutenant, making Beard the first Hillsborough sheriff to win four consecutive terms.

1978: Walter Heinrich, a Democrat and Beard's chief deputy, wins a five-person special election held after Beard steps down to run for state House of Representatives.

1980: Heinrich wins without opposition.

Walter Heinrich, who died in 2010, was elected Hillsborough sheriff four times. He ran twice without opposition. [Times files (2010)]
Walter Heinrich, who died in 2010, was elected Hillsborough sheriff four times. He ran twice without opposition. [Times files (2010)]

1984: Heinrich beats fellow Democrat Alexander Scaglione, a retired salesman, with 89 percent of the vote.

1988: Heinrich wins without opposition.

1992: Cal Henderson, a sheriff's colonel and Democrat running with Heinrich's endorsement, easily defeats Republican businessman Clifford Paramoure.

1996: Henderson wins without opposition.

Cal Henderson first won election as sheriff with the endorsement of his predecessor, Walter Heinrich. [Times files (2003)]
Cal Henderson first won election as sheriff with the endorsement of his predecessor, Walter Heinrich. [Times files (2003)]

2000: Henderson handily beats write-in candidate William Wesley Godwin, 46, a self-employed Mango tree surgeon who on Election Day was sitting in the county jail on six counts of driving with a suspended license.

2004: David Gee, a Republican who served as Henderson's chief deputy and ran with his endorsement, beats Godwin. Gee had trounced retired FBI agent Lane Bonner in a Republican primary. Two other would-be challengers left the race because they could not raise enough money.

2008: Gee wins without opposition.

2012: Gee wins after defeating a write-in candidate named Robert O. "Grumpy Bob" Wirengard. No Democrat filed to run.

David Gee, shown here with former State Attorney Mark Ober, announced his retirement one year into his fourth four-year term. [Times files (2016)]
David Gee, shown here with former State Attorney Mark Ober, announced his retirement one year into his fourth four-year term. [Times files (2016)]

2016: Gee wins without opposition.

2017: Gee abruptly retires and recommends that Gov. Rick Scott appoint one of Gee's colonels, Chad Chronister, to fill the post until the 2018 election. No other applicants filed for the appointment.

Times staff writer Tony Marrero and senior news researcher Caryn Baird.