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Orange sheriff candidate defends arrest record: I know 'what both sides of an arrest feel like'

Records show that Darryl Sheppard has been arrested in Florida at least 13 times since  1998 — on charges ranging from driving with a suspended license to battery and motor-vehicle theft.

Darryl Sheppard is an outlier in the race for Orange County sheriff. He’s the only candidate on the three-man ballot who’s never served as a sworn law-enforcement officer and the only one running on a partisan ticket.

Sheppard is also the sole candidate with an arrest history.

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Records show that Sheppard, who is running as a Democrat, has been arrested in Florida at least 13 times, on charges ranging from driving with a suspended license to battery and motor-vehicle theft.

Many of the charges were dropped or dismissed by prosecutors. Some of the cases are still pending; Sheppard, 35, has not been convicted of a crime.

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Sheppard, a venture-capital CEO who never served as a officer but was issued a “Certificate of Compliance” by the Florida Department of Law Enforcement after undergoing training in 2003, says his experience with law enforcement allows him to see arrests from two points of view.

“I am the only candidate in this race to know what both sides of an arrest feel like,” Sheppard said in a statement to the Orlando Sentinel. “I am the only candidate in this race to have to explain to employers, voters and now journalists about the mistakes I have made.”

Darryl Sheppard arrest mugshots.
Darryl Sheppard arrest mugshots. (Orange County Jail)

His history includes at least three arrests for driving with a suspended license, three for failure to appear and one for a DUI.

In all of those arrests, charges were dropped or adjudication was withheld. Sheppard claims he currently has a valid license without restrictions.

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In 2012, Sheppard was charged with two misdemeanor counts of battery — both later dismissed — after he was accused of groping one woman and punching another in a downtown Orlando parking garage.

The women said Sheppard was following and harassing them in the garage when he grabbed one woman’s rear end, according to court records. The other woman said she yelled at Sheppard to stop and he responded by punching her in the face.

When Sheppard tried driving away from the scene, the first woman jumped on his car to take the keys out of the ignition, causing Sheppard to say, “Get off my f------ car you stupid b----,” according to his arrest report. Police said Sheppard hit the woman with his car when he tried driving away.

When officers arrived, the woman who said she was punched was lying on the ground, bleeding from the mouth, court documents show. Sheppard told officers that he “was trying to flirt with one of the girls when they got mad and attacked me for no reason,” according to court documents.

Referring to the battery arrest, Sheppard said the allegations “weren’t true.” A police report says five witnesses corroborated the women’s version of events.

In February 2017, Sheppard was charged with trespassing and felony motor-vehicle theft after officers found him in a rented Mercedes that was supposed to be returned the previous December.

Sheppard described the situation as a “contractual misunderstanding.” Prosecutors determined the case “was not suitable for prosecution,” according to court records.

Sheppard also currently has three charges of passing worthless checks pending in Leon County.

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Joe Lopez, a former Florida Highway Patrol chief who’s running for sheriff as an independent, said an arrest and driving history like Sheppard’s should disqualify applicants who are seeking positions in law enforcement.

“Law enforcement officers are entrusted with the responsibility of keeping our communities safe from crime and corruption,” Lopez said. “Therefore, before we can hold the community accountable we must hold [ourselves] accountable.”

“To become a law enforcement officer, you must have unquestionable integrity, since law enforcement officers are held to a higher standard,” he said.

John Mina, also running for sheriff as an independent and Orlando’s current police chief, declined to comment directly about Sheppard’s arrest history. A spokesman for Mina’s campaign said, “That’s quite concerning to learn, but we’ll leave it to the voters to make that decision.”

Sheppard said that, although he is the only candidate with an arrest history, voters should look at how Mina and Lopez performed in their duties before determining who gets their vote.

“While I have an arrest record, they have records on the job,” Sheppard said, specifically referring to Orlando police officers who were accused of using excessive force under Mina’s command. “That doesn’t mean they’re any better or worse than me. That’s the record that matters the most: how they’re doing their jobs.”

The Orange County sheriff election is on Nov. 6.

Scroll down to read Darryl Sheppard’s full statement.

Michael Williams can be reached at miwilliams@orlandosentinel.com, 407-420-5022 or @michaeldamianw.

Sheppard Statement

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