One day this summer Gary Pruitt delivered a two-minute pitch to Plant City voters, describing what could change if he were picked to be Hillsborough County’s next sheriff. Among his promises: He would diversify the ranks. But the uniformed competitor on stage with him, Chad Chronister, didn’t have to wait for votes. He had already been appointed Hillsborough sheriff by Florida’s governor, after the 2017 resignation of Sheriff David Gee. Chronister had already installed a woman as chief deputy, an agency first, and, in another first, would soon promote an African-American to colonel.Such is the plight of the retired Tampa cop and current mall security chief who is challenging Chronister, a man with more than a year’s head start. As Pruitt advocates for a citizens advisory committee, the sheriff packs his schedule with community meetings. While Pruitt pushes to unionize deputies, Chronister touts progress in making their patrol cars safer and hiring reinforcements.Pruitt, 50, casts himself as an outsider who could foil an agency tradition of passing the sheriff’s badge to an anointed successor.BACKGROUND: New sheriff won over those in power. The voters? They don’t get a say"The Hillsborough County Sheriff’s Office has been handing down the office of sheriff since 1964," Pruitt told the crowd at a Plant City candidate forum. "That process is what actually has allowed my opponent to campaign in uniform."But observers say Pruitt may be too much of an outsider, one who hasn’t marshaled the resources or mobilized the grassroots campaign he needs to topple Chronister, who has raised a record $1.2 million.Further complicating matters, Pruitt’s personnel and court records are blemished by personal and financial struggles.A Republican-turned-Democrat who left the party after Donald Trump was elected, Pruitt insists he’s ramping up his campaign in the home stretch. "I’m a freight train," he said in late September. "I’m making slow moves but I’ve still got time."•••Pruitt was born in Lima, Ohio, and raised in nearby Wapakoneta, a city of about 10,000 in the northwest part of the state. He was 15 when he moved to Tampa with his mother and older sister.He joined the police academy in 1990 with a high school equivalency diploma and remained with the Tampa Police Department for 25 years. For about 15 years, Pruitt worked as a patrol officer. Later, he was promoted to detective and assigned to a drug squad, then made supervisor of a Rapid Offender Control Squad focused on high-crime areas."He was fair and he was honest," said Sgt. Robb Fannin, who worked under Pruitt on the ROC Squad. "He made us be very, very thorough."After a stint tackling illegal dumping in East Tampa, Pruitt made corporal and was assigned to a midnight patrol squad. He served as acting sergeant for about six months until Sgt. Doug Burkett took over. Burkett called Pruitt an excellent second-in-command and a good mentor to officers."He was the type of guy who led from the front," Burkett said. "He never asked them to do anything he wouldn’t do himself and they respected him for it."Shortly after retiring from the department, Pruitt took a job as director of security for Westfield Citrus Park mall, where he oversees a staff of more than 20.Sean Cronin was Pruitt’s assistant director for about a year. "He’s willing to listen to you and he’s very respectful to his employees," Cronin said. "I think he definitely has what it takes to be sheriff because he has a knowledge of the working man. He’s willing to get in there and get his hands dirty."•••Pruitt has a few dings in his Tampa police personnel file. The most serious came in 2011 over a rules violation that would also upend his personal life.That year, supervisors learned Pruitt was in a "close, personal relationship" with a female subordinate, a violation of department and city policies, according to a warning letter in his file. Pruitt said he considered fighting the disciplinary action at the time because the woman did not report directly to him. He fathered a child with her, was sued over paternity and then fell behind on child support payments, records show.Pruitt said the affair led to a separation from his wife, Yvonne, with whom he has two daughters. The couple later reconciled and recently celebrated their 25th anniversary. They live in Westchase.County records show Pruitt has a history of financial problems, including bankruptcy, foreclosure and wage garnishment. He said most of the financial troubles stemmed from expenses associated with the paternity suit, child support payments and the separation from his wife. "There was double rent and double everything for a while," he said.•••Pruitt said he switched parties after Trump’s election because "he’s not representative of me." He figured he would get more support as a Democrat than as a no-party candidate, but he’s also leery of turning off voters weary of partisan politics.Of the $12,740 Pruitt raised through September, $10,000 came out of his own pocket, records show. Most of the money went toward a $10,663 filing fee. He said his lack of campaign contributions is a positive. If he wins, he says, he won’t be beholden to anyone. Ione Townsend, chairwoman of the Hillsborough Democratic Executive Committee, said Pruitt hasn’t contacted party officials to ask for help with his campaign."I have not seen a ground game and I don’t know how you win without one," Townsend said. "It’s unfortunate because if this blue wave thing really happens, he could stumble into a victory, but because he’s not engaged with the county party, I think it’s a long shot for him."On his bare bones campaign website and Facebook page, Pruitt outlines four priorities. He says he will work to make the agency staff more reflective of the county’s increasingly diverse population. He promises to create a citizen advisory committee to give residents a say in Sheriff’s Office policies and procedures. He wants transparency. He says the agency has been dominated by a "good ol’ boy" system.And he wants to unionize the ranks from sergeants on down. Pruitt says some deputies want to unionize but fear retribution.Hillsborough deputies voted by a large margin in 2008 to leave the West Central Florida Police Benevolent Association. At the time, union members said the vote reflected confidence in then-Sheriff Gee.The PBA has endorsed Chronister. Last month, union president Nick Marolda lauded Chronister’s diverse career at the agency and his support of community-based policing and investments in technology.In an interview, Marolda said the union hasn’t heard from deputies interested in starting the process to unionize. He said union officials have heard good things about Chronister."We got a sense he’s really looking out for his people and he’s an innovative guy," he said.Chronister said the previous union contract was too restrictive, limiting the sheriff’s ability to act in deputies’ best interests."If they need the union to come in, then I’m not doing my job," he said.As for Pruitt’s call for a citizen advisory committee, Chronister noted the public gets to weigh in through minority councils that attend shooting review board meetings. He points to progress he’s already made to make his command staff more diverse.Chronister and his supporters insist the grooming process allows someone to learn the complexities of a sprawling office with more than 4,000 employees and a $430 million budget.Pruitt says voters can trust him to get up to speed."I can come in there and learn what we should be doing," he said, "not just what we’ve always done."Contact Tony Marrero at [email protected] or (813) 226-3374. Follow @tmarrerotimes.