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.
Federal investigators probing the activities of Greenberg and his allies are aware of his claims about his involvement with Sheppard’s campaign, according to one person who has spoken with them. It’s not clear if they are actively investigating it — but one of the other candidates from the 2018 race said they should.
The bad checks and last-minute loan weren’t the only unusual activity around Sheppard’s 2018 candidacy. His campaign twice shared fake social media posts on its Facebook page meant to look like then-Republican President Donald Trump was supporting one or both of Sheppard’s rivals, Mina and Joe Lopez. Sheppard’s campaign also published photos suggesting he had the support of Democratic U.S. Rep. Val Demings — the wife of outgoing Orange County Sheriff Jerry Demings — which prompted the congresswoman to call Sheppard “totally unfit” for office.
“I guarantee all those roads are going to lead to Greenberg,” Lopez said of the tactics.
Fritz Scheller, an attorney for Greenberg, declined to comment.
‘I like my odds’
One of the most powerful elected offices in Central Florida, the job of Orange County sheriff came open early when Jerry Demings decided to step down in the middle of his term to run for county mayor.
Two candidates with traditional backgrounds soon emerged in the race to replace him: Mina, who was then the chief of the Orlando Police Department, and Lopez, a former Florida Highway Patrol chief.
But Mina and Lopez shared a vulnerability: Both were former Republicans who missed a deadline to switch parties and run as Democrats in the race. They were forced to run without any party affiliation — leaving an opening for a Democratic candidate in Orange County, which has become a stronghold for the party in recent years.
That’s where Sheppard came in.
A former club owner and first-time candidate for office who described himself as a venture capitalist, Sheppard carried a lot of baggage: He’d had multiple arrests and bankruptcies in the past and, as he entered the race, warrants for new arrests were being issued in Tallahassee because Sheppard had failed to make payments on more than $6,000 in home furnishings from the rental company Aaron’s and had written bad checks to an air conditioning repair company and the Tallahassee city government, court records show. A home Sheppard owned in the city had also been foreclosed upon and one of his businesses was carrying a lien related to unpaid sales taxes.
But Sheppard was a Democrat who could appear with a “D” next to his name on the ballot.
Some of Greenberg’s political allies were already working with Lopez and Mina: Mike Shirley, a local political consultant who had worked on Greenberg’s campaign for tax collector, was hired by Lopez, and Eric Foglesong, another local consultant, was hired by Mina. Both Shirley and Foglesong also worked as contractors for Greenberg at the Seminole County Tax Collector’s Office.
But Sheppard said Greenberg reached out to him shortly after he filed to run and pledged support for Sheppard’s campaign during a meeting at a local Irish restaurant. Sheppard said he assumed Greenberg chose to support him because of Sheppard’s policy positions, such as support for a citizen review board to investigate claims of police brutality.
“I never knew the motive for some of the characters that I ended up coming across during that campaign,” Sheppard said.
The campaign almost failed at the starting line. On the final day to officially qualify for the race, Sheppard’s campaign wrote a $10,136.94 check to pay the qualifying fee — even though, records would later show, there wasn’t enough money in his campaign account to cover the check.
That was a Friday. On Monday, Sheppard called the Supervisor of Elections’ office and asked them not to cash that check, which he later replaced with a new cashier’s check, according to records filed in a later civil lawsuit. But then the bank stopped that check, too.
A day later, Sheppard provided yet another cashier’s check — covered by a last-minute loan of nearly $6,000 he provided to his own campaign.
It was amid that qualifying chaos that Greenberg texted a fellow Seminole County Republican claiming “I have” the Democratic candidate in the Orange County sheriff’s race.
“OPD chief Mina has to run as an NPA because he missed the cutoff to file as a democrat by 4 days,” Greenberg wrote in a follow-up message. “Two NPAs and one Dem on the ballot to replace Demings. I like my odds.”
Lopez: ‘Expose the corruption’
As the campaign continued, Sheppard’s personal finances appear to have improved. In July, for instance, the Florida Department of Revenue withdrew a lien against one of Sheppard’s businesses after it said the $300 in unpaid penalties was satisfied.
In August, prosecutors in Leon County dropped charges against Sheppard related to bad checks he wrote for more than $600 to an air conditioning company and roughly $500 to the city of Tallahassee after Sheppard paid restitution, according to court records. And in September, they dropped charges related to more than $6,000 in Aaron’s furnishings after Sheppard “paid for all his leased property and closed his account with the victim,” court records show.
Meanwhile, other people in Greenberg’s circle helped to boost Sheppard’s bid for sheriff. For instance, a local blogger and Greenberg promoter named Jacob Engels published a story accusing Orange County Democratic Party Chairman Wes Hodge of trying to bribe Sheppard out of the sheriff’s race. Hodge has said the allegation was untrue.
It was also during an antagonistic Twitter exchange with Hodge when Greenberg wrote a message implying he would soon “own” the Orange County Sheriff’s Office. Greenberg has since deleted that Twitter account, though Hodge provided the Sentinel with a screenshot.
Sheppard said he expressed appreciation to Greenberg for supporting his campaign but never promised any favors if he were elected. He said that neither Greenberg nor any of his allies ever paid him any money beyond $600 in campaign contributions from Greenberg and one of his businesses. Sheppard said he paid his qualifying fee with his own money.
Eventually, the rumors that Greenberg was working behind the scenes on Sheppard’s behalf became so strong that Joel Hawksley, a local Republican political strategist who had been working on Lopez’s campaign, said he asked Greenberg about it during a face-to-face meeting.
“I just said, ‘What do you get out of helping Sheppard?'” Hawksley said.
Greenberg, Hawksley said, responded by saying, “If he wins, we have control of the Orange County Sheriff’s Office.”
Lopez said he asked a similar question of Shirley — the campaign consultant he had hired for his own campaign who was also working for Greenberg at the Tax Collector’s Office. Lopez said Shirley told him to ignore Greenberg’s involvement with Sheppard.
“Shirley says, ‘Listen, don’t worry about Sheppard, he’s not your threat,'” Lopez said. “Focus on your race. Mina is your threat and that’s what you need to focus on.'”
Lopez says he now suspects that Greenberg and his allies were hoping he and Mina would erode each other’s support, creating an opening for Sheppard.
Shirley did not respond to requests for comment.
Mina also had his own consultant troubles in the race. A few months after the election ended, Foglesong, who worked on Mina’s campaign and had also been a Greenberg contractor at the Tax Collector’s Office, was arrested and charged with stealing money from a political committee that was set up to help Mina’s campaign.
Foglesong later pleaded guilty to grand theft. In a statement in response to a request for comment, he said his efforts helped Mina get elected and said he worked to thwart Sheppard’s campaign.
Mina declined to discuss the race or Greenberg’s involvement in it.
“I have always believed it’s important in these constitutional offices to select candidates who have a longstanding record in the communities they serve,” he said in a written statement. “I trusted the voters of Orange County to do the right thing — and they did.”
But Lopez said he’s hopeful that investigators will dig deeper into the 2018 sheriff’s race and get to the bottom of all the oddities. Both Sheppard and Lopez ran for sheriff again in 2020, losing to Mina, who cruised to re-election as a Democrat.
Dirty tricks in local elections have recently come under increased scrutiny in Florida after a former state lawmaker in Miami was arrested for allegedly hiring a friend to run as a vote-siphoning independent in a South Florida state Senate race.
Similar candidates surfaced in two other important state Senate races, including Senate District 9 in Central Florida, where investigators probing Greenberg’s activities have, according to the New York Times, learned of a conversation between two Greenberg allies — U.S. Rep. Matt Gaetz and lobbyist Chris Dorworth — about lining up a spoiler candidate to help elect their friend, Republican Sen. Jason Brodeur. Jestine Iannotti, who ran as an independent in the District 9 race but did not campaign, had help from Foglesong, who likely wrote the check for her filing fees.
Greenberg, meanwhile, was accused of using underhanded tactics against three rivals to his own 2020 re-election bid: Democrat Lynn “Moira” Dictor argued Greenberg was behind an associate’s decision to run as an independent under a name similar to hers. Greenberg’s predecessor, Ray Valdes, claimed in court that a Greenberg associate had pressured him to push Republican and eventual victor J.R. Kroll out of the race. And an anonymous smear campaign by Greenberg against another Republican rival, Brian Beute, led to Greenberg’s initial arrest on stalking charges, after which Greenberg resigned and dropped out of the race.
“A lot of people are concerned about the way everything went,” Lopez said. “Hopefully some of this stuff will expose the corruption and people can have faith in the electoral system.”
jgarcia@orlandosentinel.com; amartin@orlandosentinel.com
