The 2016 election brought another easy win for Pinellas County’s incumbent sheriff.
Republican Bob Gualtieri cruised back into office with almost 80 percent of the vote against an opponent who ran with no party affiliation. The race drew no Democratic contenders.
Gualtieri is running again, but a lot has changed in four years.
The political landscape is more divisive than ever in a presidential election year during a pandemic and nationwide Black Lives Matter protests. Even the usually uncompetitive race for Pinellas sheriff is getting interesting.
Not only has this year’s race drawn two Democratic candidates, but one of them — a retired Sheriff’s Office communications maintenance supervisor named Eliseo Santana — has raised more than $25,000 in a few weeks thanks to donors outside Florida and left-leaning political organizations.
His opponent, James McLynas, has raised less than half of that amount in his second run for the office. But the vast majority of his donations have come from within the county and state.
The sudden national interest in a local sheriff’s race is in line with what experts call an ongoing trend of nationalization — introducing national issues into local elections.
One way that’s played out in sheriff’s races is through immigration. It’s a national issue but sheriffs have played a role in enforcement — and few local sheriffs have played as big a role as Gualtieri has.
It’s likely national issues will continue to influence this election cycle as demonstrators in Tampa Bay and around the country continue to protest police brutality and racism in response to the May 25 death of George Floyd, who was killed by a Minneapolis police officer.
“He (Santana) is obviously being supported by progressive Democrats from across the country,” said University of South Florida political science professor emeritus Susan MacManus. “A sheriff’s race at a time when criminal justice and law enforcement reform are at the top of progressives’ lists — it’s very easy to understand how that would happen.”
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Days after Santana filed to run for sheriff on June 4, the money started rolling in, according to financial filings compiled by the Pinellas County Supervisor of Elections.
A $1,000 check came in from a retired woman in New York City, then another from a Connecticut business consultant. Over the next few days, more big checks came in from a San Francisco tech executive, a Portland lawyer, a New York City psychologist, a Seattle business consultant.
The total in that first fundraising cycle was almost $25,000. It slowed down in the second cycle, which ended June 26.
About 9 percent of the $27,055 Santana has raised so far has come from within Pinellas County, and about 29 percent from donors in Florida, according to a Tampa Bay Times analysis of Santana’s campaign contributions.
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The local donations tend to be smaller, in the range of $25 to $100. Larger donations came from statewide groups, including $1,000 each from the Florida Public Services Union and the political organizing arm of the Florida Immigrant Coalition.
But most of Santana’s donations of $500 or more poured in from donors in large metro areas outside the state. A handful more came from outside political action committees, such as United for Progress, a Washington, D.C. super PAC backed by billionaire and Democratic donor George Soros.
In response to a request for an interview about the donations, Santana, 62, sent a statement to the Times saying he’s “proud to earn the support of so many people who share my passion for reform.”
“My message is resonating in Pinellas, Florida, and across the nation as we have a difficult — but long overdue — conversation about police brutality, racism, and institutional injustice,” he said.
However, Santana did not respond to a follow-up question about how donors in faraway states learned of his campaign.
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Election and campaign finance experts said that the nationalization of local races and the power of digital fundraising platforms could be at play.
Incumbent sheriffs have a huge advantage, said Michael Zoorob, a doctoral student in government at Harvard University. It’s an especially tall order when going up against someone like Gualtieri, who has taken on several high-profile roles and has developed powerful political allies in Florida and beyond.
One way to get attention as a lesser known local candidate is to align your campaign with national issues.
Zoorob published a paper about how several progressive sheriff’s candidates in 2018 successfully beat incumbents by linking their campaigns to opposition of President Trump through the issue of immigration enforcement. Outside money, and support from national political organizations, played a key role in some.
“People pay a lot more attention to presidential elections than they do with local elections,” he said. “If you want to energize your campaign, you kind of have to link your local election to a national one.”
MacManus said social media can spread the word too, as can organizations, like Emily’s List, that raise money for candidates based on a certain issue.
Those resources give prospective donors a wider array of choices, as opposed to just candidates in their own communities.
“This is not a new thing,” MacManus said. “It’s just that technology … has made it much easier to put together fundraising blasts that are what we call micro-targeted to certain individuals.”
McLynas, who will face Santana in the Aug. 18 Democratic primary, said in an email to the Times that the donations signal to him that Santana is “a spoiler candidate and is backed by many of the very people that want to keep a corrupt Sheriff like Gualtieri in power.”
Ever since a personal dispute with the agency dating back to 2012, McLynas has made it his mission to unseat Gualtieri.
His campaign website has a section detailing what he sees as corruption within the agency. His Facebook page includes photoshopped memes of Gualtieri as Hitler, or with “LIAR” typed across his forehead. (Gualtieri has and continues to call McLynas’ claims baseless.)
McLynas, a former collision repair and vehicle inspection business owner, has raised most of his campaign money in Pinellas: About 71 percent of the roughly $16,200 in cash and in-kind donations he’s raised so far is from the county, and about 85 percent is from within Florida.
“Unlike the other candidates,” the 61-year-old said, “every single one of my donors is a real person who knows me, knows what I stand for and wants to take part in a historical change of ending everything that is wrong with the local police industry.”
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Santana is making his first run for sheriff.
But he’s run for local office before, most recently in this year’s Clearwater City Council election. He lost. He also ran unsuccessfully for School Board in 2016.
Santana said he decided to run for sheriff at the last minute, after watching the video of Floyd’s death. Santana, who is Puerto Rican, said it reminded him of the racism he’s seen in his own life, particularly, he said, when the Sheriff’s Office hired him as an electronic technician in 1980. He recalled a top official giving him extra scrutiny on a background check and drug test.
The organization hasn’t changed much, he said, pointing to the agency’s command staff, which has one person of color out of 32 people.
“I just don’t see a change in the culture or in the actions of our current administration,” he said. “So here I am. I’m offering a good alternative. I’m offering to use my experience, my heart, to be able to make our county better.”
Blue Ticket Consulting is running Santana’s campaign. The St. Petersburg firm has represented Tampa Bay progressives including Mayor Rick Kriseman and Hillsborough State Attorney Andrew Warren.
McLynas is making his second run for sheriff after his unsuccessful bid as a no-party-affiliation candidate in 2016.
Among his biggest goals is to end marijuana enforcement, effectively legalizing the drug, and to clean up what he calls corruption inside the Sheriff’s Office, such as the agency’s use of a controversial cellphone tracking device or facial recognition software.
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Beyond that, the broad strokes of his and Santana’s platforms are similar.
Neither has law enforcement experience, which both consider an asset to bring in new ideas and change the culture of the agency.
Their ideas emphasize implementing criminal justice reform by demilitarizing the police and pulling back on arrests for low-level, non-violent offenses.
They’re both in favor of issuing body-worn cameras to deputies, a move that Gualtieri has long opposed. They also want to reduce uses of force, create a more inclusive culture within the agency, and reallocate budget money toward community and social services.
The Democratic Party of Pinellas isn’t supporting one candidate or the other in the primary, said vice chair Johnny Boykins. They’ll wait to support the winner for the Nov. 3 election.
“I think it’s a good thing that we are seriously trying to run a race for sheriff, which we haven’t done in a few cycles,” Boykins said. “A lot of people are looking at local elections in a much different way, because right now only local leadership is giving solutions.”