Get in a conversation with Eliseo Santana, and he’ll find a way to bring up his grandchildren.
There are 13 in all, 12 girls and a boy, ages 1 to 17. They’re a constant presence in Santana’s life, waving signs or handing out flyers or ironing “Santana for sheriff” logos onto face masks.
The longtime Clearwater resident says they’re his inspiration as he challenges Pinellas County’s powerful and well-known sheriff.
“It’s not my campaign,” Santana said. “It’s our campaign to make a change and make a difference.”
The 62-year-old Democrat has little name recognition compared to Sheriff Bob Gualtieri. But Santana’s campaign against the county’s most entrenched Republican is buoyed by a summer of protests against the police status quo and a massive push for progressive voters to go to the polls. He’s even been endorsed by Sen. Bernie Sanders.
Santana is a true family man, supporters say, with deep roots in Pinellas and a strong record of civic involvement and advocacy for the county’s Latino community. Even his critics agree that he’s a nice, likable guy.
But the question facing Santana and voters is whether he can run one of Florida’s largest law enforcement agencies, its 3,000-member staff and a budget in the hundreds of millions.
“We have a clear choice in this election: keeping the status quo now or truly having a dynamic change to bring us into the 21st century,” he said.
He worked at the Sheriff’s Office for 30 years, but as a civilian communications maintenance worker and manager, not a sworn deputy. He has no experience leading any government agency and has never held elected office. He lost elections for School Board in 2016 and Clearwater City Council in March.
But Santana said he brings a fresh perspective to the job and understands how the Sheriff’s Office works.
“You don’t have to be the best at everything,” said Mike Gandolfo, former president of the Pinellas County Teachers Association, which endorsed Santana for a school board seat. “You just have to know the right people who you can rely on. And I think in that regard, Eliseo’s pretty dogged.”
Critics say his lack of management and law enforcement experience is too big to overcome.
“I don’t think I’ve ever had an election where the choice was so clear as a citizen,” said retired sheriff’s captain Jim Main, a Gualtieri supporter who supervised Santana for several years. “If Eliseo is qualified for sheriff, I’m qualified to be president.”
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Santana was born in the Bronx to Puerto Rican parents. His parents moved around a lot looking for manufacturing jobs.
He spent first and second grade in Puerto Rico, solidifying Spanish as his first language. In 1976, he graduated from high school in Worcester, Mass. Then he joined the Army and learned to repair electronics — a job he came to love. He married his wife Nereida in 1978. Two years later he left the Army and joined his parents and wife in Florida, settling in Pinellas County.
The Sheriff’s Office hired him in December 1981 as a communications technician. In 1996 he was promoted to his highest-ranking job as communications maintenance supervisor, according to his agency personnel file. Santana fixed and maintained equipment such as deputies' radioes, modernized the jail surveillance system and helped establish its video visitation program for inmates.
His employee reviews were complimentary for the first half of his career, earning him many “better than satisfactory” marks — the second highest rating.
“His drive for self-improvement is a benefit to the department and a source of inspiration to his fellow workers,” a supervisor wrote in 1988.
They grew more tepid, and at times critical, particularly during his time as a manager. A few mentioned he was late turning in evaluations for his employees, struggled with time management and meeting preparation, and made grammatical and spelling errors in reports.
When asked about those reviews, Santana attributed them to systemic bias at the Sheriff’s Office — a point he’s hammered on in his campaign as one of the reasons why he feels so strongly that the agency needs a culture change. He said his supervisors were all white, and he was often the only person of color in the room.
“It’s just a classic situation of having the only person of color in that capacity,” he said. “The standards of measurement were not equally applied.”
His former boss Main, who is white, said Santana was treated fairly.
Santana retired from the Sheriff’s Office in 2012. His foray into politics would come a few years later.
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Santana’s first run for office was four years ago for Pinellas County School Board. He said he was inspired by the 2015 Tampa Bay Times investigation “Failure Factories,” which documented the struggles of Black students at five St. Petersburg elementary schools and other schools across the district.
He lost, but his community involvement was ramping up. He joined the League of United Latin American Citizens and started his own chapter in Pinellas, said Lydia Medrano, director of the organization’s Tampa Bay district. He formed a nonprofit, Puerto Rico Connect, to help Hurricane Maria evacuees.
“He gets very involved and he wants to do things for the community,” Medrano said. “He cares about everybody.”
But he was also coming off a rough patch financially. Court records show Santana went through several mortgage foreclosures, including in 1999 and 2012. He filed for Chapter 7 bankruptcy in 2013, which he said was due to the Great Recession. The bankruptcy case was closed in 2015, but another court case popped up last year in which Santa owed over $4,000 in credit card debt. A judge ruled against him this year, according to court records.
Santana said he needed the money to help his daughter pay for medical bills associated with a life-threatening pregnancy complication and that he would do it all over again.
In March he ran unsuccessfully for Clearwater City Council. Then in May, George Floyd died in Minneapolis police custody — the catalyst, Santana said, for his last-minute decision to run for sheriff.
Watching the video of the white police officer kneeling on the neck of Floyd, a Black man, Santana said he thought his 11-year-old grandson, who is Black and Latino.
“I just saw the future for young men like him,” Santana said. “They will be judged by the color of their skin, or their economics or both and not by the character they have and not by who they are.”
• • •
The overall message that Santana conveys at candidate forums is that he wants to create a more inclusive Sheriff’s Office that represents the community it serves.
He often points out that Gualtieri’s command staff is almost all white. Promotions are controlled by a “good ole boy” network that he says he experienced himself in the mid-1990s when a white coworker got a promotion over him even though Santana said he was more qualified. He wrote a memo challenging it, Santana said, and received the promotion instead. The memo wasn’t in a copy of his personnel file released to the Times. A sheriff’s spokesman said he couldn’t confirm or deny its existence.
Gualtieri said his agency is representative of the community and that promotions involve a rigorous process.
“Mr. Santana, because he doesn’t have any law enforcement experience," the sheriff said at an Oct. 14 candidate forum, "doesn’t understand what it takes to rise to the level of having the right experience.”
One of Santana’s biggest attacks on Gualtieri stems from immigration policy and the sheriff’s support of President Donald Trump. Gualtieri helped author a controversial sanctuary cities ban and worked with Immigration and Customs Enforcement to allow local jails to hold undocumented immigrants accused of crimes. Santana said he’ll end the program in Pinellas.
The rest of his platform includes many of the tenets of a progressive law enforcement campaign.
He supports creating a civilian review board. He wants to put resources into a police-social work program to better address people with mental illness or those suffering from substance abuse. He wants to bolster training for deputies to de-escalate tense situations before they turn violent. And he wants all deputies to wear body-worn cameras.
Some of that is already in place or in the process. Gualtieri announced in September that he was expanding a team he started to handle mental health-related calls. And this month the sheriff, who resisted the cameras for years, will start a field trial next week. Gualtieri said those decisions weren’t politically motivated.
His opponent told the Times this: “Thank you, sheriff, for endorsing my policies.”
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