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A smudge of tarnish appears on Hillsborough sheriff's golden boy

Some meetings you never forget.

My brush with Rocky Rodriguez was one of those.

It was at a Democratic Party event for Gov. Lawton Chiles at a Tampa hotel around 1994. Rodriguez, the black-haired golden boy of the Hillsborough Sheriff's Office, began to brag. He knew about me, he said. And he did. He had information about my life that you don't find in the public record.

This is what I got for being on Rodriguez's enemies list. A year or so before, I had written about Rodriguez, an offense for which I was not to be forgiven. Rodriguez's name had surfaced in the Key Bank investigation. He was never accused of a crime, but he was overheard on a recorded phone call talking to a friend who was an officer of the bank that was the target of a massive money laundering investigation. The investigation collapsed when another sheriff's deputy tipped the suspects that they were being watched.

This was not the Hillsborough Sheriff's Office's finest hour. The tipster was prosecuted, and the two lead sheriff's detectives on the case were demoted. But Rodriguez, who was close to Sheriff Cal Henderson and was his chief campaign money man, got promoted.

I can't remember Rodriguez's rank then. He has risen over the years remarkably unimpeded, attracting envy, enmity and just plain curiosity as he moved up and up, finally to the rank of major making more than $100,000 a year. He was put in charge of special operations. That covers everything from airplanes to narcotics. It was a glam job, and it gave Rodriguez power to use as he wanted.

Last May, when he learned that he might be under criminal investigation for loansharking, Rodriguez gathered up a personal army of 10 detectives to tail an informant back to a secret meeting with federal and state investigators. The investigation was apparently derailed.

In September, Rodriguez used a trip to pick up a new sheriff's helicopter in Texas as a reason to stop and spend the night at a gambling casino in Biloxi, Miss. He says differently, but Chief Deputy David Gee said Rodriguez never asked his bosses if he could go. Of the five men on the trip, only Rodriguez got his hotel room "comped." Either he is a regular at the casino or for some other reason he is special. Getting a room comped means you get it for free.

The most remarkable part of Rocky Rodriguez's career is how much of a blank check he has gotten from his boss and campaign fundraising beneficiary, the sheriff.

Henderson has had little opposition as sheriff, and fundraisers presumably come and go. Yet Henderson treats Rodriguez so much like a piece of prized glass that I've wondered: Does Rodriguez somehow represent other people whose approval the sheriff feels he absolutely must have?

Henderson barely raised an eyebrow about the loansharking allegations, except belatedly to the Tampa Tribune. He saw no reason to conduct an internal affairs investigation. He even endorsed Rodriguez's decision to send off his own detectives to see what was up.

Henderson also turned away complaints about the gambling side trip. He said Rodriguez's explanation washed. But that was when Rodriguez was claiming he paid for his hotel room. Now that it turns out he apparently got the room for free, and the Tribune editorial board has raised its voice in complaint, Henderson is changing his tune.

Henderson has moved Rodriguez sideways out of his glam job as head of special operations. Officials are taking a second look at the helicopter trip, even though it is far less serious a matter than the allegation about loansharking that drew in the FBI.

Henderson told the Tribune the public did not expect sheriff's employees to be gambling. Really now. What might be even more preferable is a sheriff who is not ethically challenged.

_ Mary Jo Melone can be reached at or (813) 226-3402.