Sheriff Bob Gualtieri’s very difficult dilemma

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Dressed in a uniform as crisp and sharp as a right angle, Sheriff Bob Gualtieri arrived a few minutes late for Monday’s meeting of the board of Tiger Bay. No one questioned why.

In addition to running the day-to-day operation of his office, it’s amazing Gualtieri still finds time for community involvements like Tiger Bay.  In fact, almost inexplicably, Gualtieri is the chair of the marketing committee for Tiger Bay.

As if he didn’t have enough to do already.

Because, in addition to being Sheriff, the first-time candidate is running for Sheriff. How he does on the first matter greatly impacts the second.

And therein lies Bob Gualtieri’s very difficult dilemma.

These are not easy times at the Pinellas County Sheriff’s Office.

Gualtieri recently described the office’s narcotics division as “too loose an operation,” after an internal investigations of nine employees, including one who might be criminally prosecuted.

This is the same unit that has been criticized recently by defense lawyers for tactics in conducting surveillance of customers of a hydroponics store.

As Mike Deeson recently commented, “Stolen money,” “destruction of evidence,” “criminal trespass,” and “lying” are not exactly the adjectives you want describing a law enforcement agency, much less your narcotics unit.

Gualtieri took over leadership of the Pinellas County Sheriff’s Office for retired Sheriff Jim Coats about four months ago.
One lingering issue Gualtieri is facing is the problematic narcotics division with a string of unfavorable allegations to say the least. In explaining his efforts to correct problems in the narcotics division, Gualtieri stressed that all of the allegations occurred “prior to me taking office.”

Before he became Sheriff, Gualtieri was chief deputy, the number two person in charge. He said his concerns about the narcotics division began before he became sheriff, saying “quite honestly, we had a captain out there that wasn’t taking care of business. … The supervision out there was lacking.”

Former Sheriff Coats said on Friday that when he left, “I felt that we had some issues, I had some concerns,” about the narcotics division as well. “We were going to address some staff changes. Some were made during my tenure, and some were made after I left.”

Even though I genuinely believe Gualtieri when he explains how he’s turning things around, I am reminded of the political axiom, if you’re explainin’, you’re not campaignin’.

Gualtieri is running against former sheriff Everett Rice and some other also-rans, but the race is really about Gualtieri vs. Rice.  On a long enough timeline, Gualtieri would probably defeat Rice.  Meaning, if Gualtieri had more than a year to fundraise and introduce himself to Pinellas voters, he could beat Rice.

Gualtieri is an impressive, accomplished man. He will likely receive the Tampa Bay Times endorsemen, which he can add to the endorsements of most, but not all, of the local Republican establishment, including County Commissioner Neil Brickfield, St. Petersburg Mayor Bill Foster and Senator Jack Latvala.

But at this rate, this is probably not enough to defeat Rice, who still looms large over the Sheriff’s Office.

For those who don’t remember Rice or are new to Pinellas, they may make the mistake that Rice is too far past his prime to be Sheriff again.  Some think Rice is Pinellas’ version of former Tampa Mayor Dick Greco, who lost his bid to return to office last year because, honestly, his age showed.

Rice may give, as the Times‘ Adam Smith remarked recently, THE WORST interviews. And Rice may appear a half-step slower than he did a decade ago.  But Everett Rice is still Everett Rice. He has a devoted corp of volunteers. Mary Repper is advising him. He has name recognition on par with Evan Longoria.  Even former St. Petersburg Mayor Rick Baker has endorsed Rice.

And, jeez, is Rice raising the money. He’s pulled in over $205,000 through the last fundraising report. Gualtieri’s efforts haven’t been shabby; he’s pulled in over $122,000.

Which brings me back to my point about Gualtieri’s ability to beat Rice.  On a long enough timeline, he might catch Rice, but elections are finite.  Gualtieri has until the middle of July, when ballots are mailed to early voters for the primary, to catch up to Rice.

But so long as he’s having to deal with deputies wearing Progress Energy uniforms and rogue narcotics detectives, Gualtieri may be too busy being Sheriff to win a campaign to be Sheriff.

Peter Schorsch is the President of Extensive Enterprises and is the publisher of some of Florida’s most influential new media websites, including,,, and Sunburn, the morning read of what’s hot in Florida politics. SaintPetersBlog has for three years running been ranked by the Washington Post as the best state-based blog in Florida. In addition to his publishing efforts, Peter is a political consultant to several of the state’s largest governmental affairs and public relations firms. Peter lives in St. Petersburg with his wife, Michelle, and their daughter, Ella.