'Bob Gualtieri has all of the characteristics of a good, effective leader. He is decisive under pressure. He is incredibly trustworthy and he knows how to empower people.'
Whether they follow him or not, residents of Pinellas County are treated every so often to a news conference by their Sheriff, who always delivers a fact-based presentation of some crime or crisis affecting the community.
Briefings by Pinellas County Sheriff Bob Gualtieri are not dry recitations of data, nor are they colorful folk tales akin to those delivered by Pasco Sheriff Grady Judd. But Gualtieri speaks his mind freely. When a dispute in a convenience store parking lot led to a fatal shooting in 2018, protests arose from Gualtieri’s decision not to charge Michael Drejka, citing the state’s stand-your-ground law.
“Lock him up or give up your badge,” Al Sharpton said at the time. Gualtieri responded that Sharpton should “go back to New York; mind your own business.” State authorities filed charges of their own, and Drejka was ultimately found guilty of manslaughter.
Gualtieri brought the incident up himself in his bio with the Pinellas County Sheriff’s Office. He tells his career story fully, controversies and all, and deals with critics concisely.
“I like to stay on the problems, stay on the headwinds,” he said. “The consequences are what they are and the chips are falling wherever they fall. The best place to be is for everybody to know where I stand and where we stand.”
That approach seems to be working. After being appointed in 2011 by Gov. Rick Scott, Gualtieri, a Republican, was elected in 2012 and re-elected in 2016 and 2020.
He has tackled homelessness, creating Pinellas Safe Harbor in 2011 as a place for the unhoused to find shelter, rather than sleeping in public places. The program is still running and is credited with helping thousands of the area’s homeless obtain job skills or receive care for mental health or addiction. The program has been a model in other states.
“Some people don’t want those services,” he said, “but I maintain it’s better than sleeping in a cardboard box.”
“Bob Gualtieri has all of the characteristics of a good, effective leader. He is decisive under pressure. He is incredibly trustworthy and he knows how to empower people. His communication style is clear and direct, and he is resilient in the face of adversity,” said Pinellas County Commissioner Janet Long, a Democrat who has worked extensively with Gualtieri, particularly during the COVID-19 pandemic on public safety issues.
“Bob has all of the knowledge, passion and integrity needed to manage the duties of the Pinellas County Sheriff’s Office and is highly respected throughout the County, the state and at the federal level as well.”
Gualtieri was born in Syracuse 62 years ago, the son of a District Attorney. After moving to St. Petersburg with his parents, he worked for the Sheriff’s Office as a detention deputy, patrol officer and detective.
He tried out several colleges, settling on Eckerd College’s now-defunct Program for Experienced Learners. After graduating with a degree in American Studies, he entered Stetson University College of Law. For a time he served as both Pinellas County’s Sheriff and its legal counsel.
He expects to stick around as long as he feels he is remaining effective.
“It sounds like a cliché, but I’ll keep doing it as long as people will have me,” he said. “If you ever reach a point where you are not enjoying it, you are not making change.”
It seems like a lot of folks would like to keep him around.
“Sheriff Bob Gualtieri is a true leader who has the respect of everyone,” said communications strategist Preston Rudie. “His unwavering commitment to transparency, innovation and collaboration has not only strengthened the trust between law enforcement and residents but has also set a new standard for excellence in public service.”
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Methodology
We define the Tampa Bay region as Pinellas, Hillsborough and Pasco, but can also include Hernando, Polk or Sarasota — if the politicians from those counties impact either Pinellas or Hillsborough.
We define a politician as being in office or running for office.
Being first on a panelist’s list earns the politician 25 points, second earns them 24 points and so on, to where being listed 25th earns a politician one point. Points are added and, voilà, we have a list.
Special thanks go to our experienced and knowledgeable panelists, who were essential to developing the 2024 list:Christina Barkerof the Vinik Family Office,Ashley Baumanof Mercury,Matthew Blairof Corcoran Partners,Ed Briggsof RSA Consulting, political consultantMaya Brown,Ricky Butlerof the Pinellas Co. Sheriff’s Office,Reggie Cardozoof The Public Square,Ronald Christaldiof Schumaker,Ana Cruzof Ballard Partners,Justin Dayof Capital City Consulting,Barry Edwards,Joe Farrellof Pinellas Realtors, pollsterMatt Florellof Vicidial Group,Shawn Fosterof Sunrise Consulting Group,Adam Gieryof Strategos Group, political consultantMax Goodman,Mike Griffinof Savills,Natalie Kingof RSA Consulting, political consultantBenjamin Kirby, TECO Energy Regional Affairs Coordinator Shannon Love, Merritt Martinof Moffitt Cancer Center,Mike Mooreof The Southern Group, political consultantAnthony Pedicini,Ron Pierceof RSA Consulting,J.C. Pritchett, pastor of St. Pete’s Faith Church,Darren Richardsof Tucker/Hall,Preston Rudieof Catalyst Communications Group,Amanda Stewartof Johnston and Stewart, andAlan Suskeyof Shumaker Advisors. WithMichelleandPeter Schorsch.
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