In June 2018, a financially struggling first-time political candidate who signed up to run for sheriff of Orange County was almost removed from the race because, records show, he didn’t have enough money to pay the nearly $11,000 qualifying fee.
But Darryl Sheppard, who initially gave the elections office two bad checks, saved his candidacy on the third try when he loaned himself just enough money to make the ballot. And Sheppard, the only Democrat in the sheriff’s race that year, went on to nearly win, losing to current Orange County Sheriff John Mina by only about 5 percentage points.
Sheppard had help from an unlikely ally: Joel Greenberg, then the Republican tax collector in Seminole County, who recently pleaded guilty to half a dozen federal crimes — ranging from public corruption to sex trafficking — and is now cooperating with investigators in a probe that has rocked some of the most powerful figures in Florida politics.
Behind the scenes, Greenberg told others in local politics he was orchestrating Sheppard’s campaign, according to records and interviews. One associate said Greenberg claimed to be using Sheppard to gain “control” of the Orange County Sheriff’s Office — a massive agency with a nearly $300 million annual budget and the sweeping powers of law enforcement.
“I do happen to have the only democrat on the ballot for the Orange County sheriff office race [sic],” Greenberg wrote in a text message to another Seminole County Republican, who provided a copy of the message to the Orlando Sentinel on the condition of anonymity. Greenberg sent the message about 48 hours before Sheppard finally paid his qualifying fee.
Later, in a taunting, since-deleted Twitter message, Greenberg also told the chairman of the Orange County Democratic Party, “I will own your SO,” using a common acronym for sheriff’s office.
In an interview, Sheppard said Greenberg helped his campaign by providing advice and recommending others who could help. But he said he has no idea why Greenberg would claim to have control over him. Sheppard said Greenberg never provided any financial support beyond a pair of small campaign contributions.
“That’s kind of strange,” Sheppard said.
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