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Deal with the Devil

The rise and fall of Gary Cross in Darryl Daniels’ CCSO

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This is the first in a series of stories told by eyewitnesses of ongoing controversies at the Clay County Sheriff’s Office under the current sheriff, Darryl Daniels.

Gary Cross is muscular, with close-cropped grey hair and intense blue eyes. Now retired from the Jacksonville Sheriff’s Office, his former colleagues said he was well respected and known for being tough but fair: a “cop’s cop” with a sharp business acumen and an easy rapport with officers, the public, and the business community. Though humbled by the assessment, Cross told Folio Weekly that he believes it was his standing in the JSO that paved the way for him to make one of the biggest mistakes of his life.

In 2014, when Westside Sgt. Gary Cross was two years and two months away from retirement, he received a plea through the JSO grapevine from then-head jailer Darryl Daniels. Daniels was running for Clay County sheriff and wanted Cross, a casual acquaintance, to help him. Daniels told Cross—and everyone else—that “the Lord” had told him to run. “I figured I was not going to argue with the will of the Lord,” Cross said. He joined the campaign.

Daniels employed a well-known political consultant, who set the campaign strategy, and Cross did the “leg work.” He did a lot of it, too. “I worked upwards of 40 to 60 hours a week at no cost to him,” Cross said.

Once he retired, Cross worked even harder, getting involved in fundraising. To potential donors, he sold Daniels as a “godly man” and a solid citizen who would not forget his supporters.

In 2016, with four former law enforcement officers in the race, Daniels won by a slim margin and became the first African American ever elected sheriff in Clay County. Although he credited his win to his own hard work, many in the campaign credited Cross.

Hoping to enjoy his retirement, Cross was instead convinced to join the new sheriff’s command staff. He was elevated to the rank of chief and charged with community and governmental outreach. Cross developed community programs and created memorable slogans for the CCSO, which are still used. He started the now infamous neighborhood walks, a prime campaign tool for Daniels today.

But Chief Gary Cross soon found himself in a bind. During the campaign, Daniels promised members of the CCSO he would appoint an undersheriff from within the ranks; he also gave his word he would not bring in retired and active duty JSO officers. After the election, however, he reneged on both promises. Some officers felt betrayed as the new sheriff brought in JSO officers and promoted them above their CCSO peers. Cross was often treated with suspicion and animosity. He accepted the rancor with no acrimony because he knew, in their position, he would probably feel the same.

“After joining the CCSO,” Cross recalled, “I began to see a disturbing side of Darryl Daniels that I had not seen before. He looked down on people, as if he was above them. In my opinion, his leadership skills were non-existent.” Cross said Daniels was persistently absent. When he was there, he frequently had his young, divorced chief financial officer in his office with the door closed—sometimes locked.

Cross also noted Daniels’ obsession with his image. The JSO, twice the size of the CCSO, had two public information officers at that time; Daniels had four. At Sheriff Daniels’ directions, the PIOs spent a majority of their time promoting the sheriff like he was a movie star. He ordered drug busts that typically netted few arrests, but his PIOs made videos of him as he preened in a long dark coat, drinking coffee and warning bad guys to stay out of Clay County. He typically left after filming.

A few months after Daniels took office, he abolished Cross’ position and put him in internal affairs. Then, after an unrelated post on Cross’ Facebook profile, Daniels demoted him to lieutenant. Sources suggest that Daniels resented Cross’ role in his election. While the sheriff was increasingly hostile, supervisors recognized Cross’ efforts with “exceptional performance” evaluations. Still, it was clear to all that the sheriff wanted Cross out. Daniels accused him of leaking information to the press, until it was revealed that Daniels himself was the leaker.

The sheriff had Cross reprimanded and “restricted to his office” in April 2019, citing spurious ethical concerns. Then, in May, Daniels’ infamous sex scandal broke on television screens across Northeast Florida. He ordered the arrest of his pregnant mistress of six years after his wife confronted the couple.
Cross was demoted, prompting his resignation, effective August 8, 2019. Meanwhile, because he felt his “policeman bill of rights” had been violated, Cross asked for a public hearing as allowed by Florida Statute 112. The next day, bright and early, a representative from CCSO IA came knocking on his door and informed Cross that his demotion had been rescinded and he was restored to full rank. Since there was no demotion and no discipline, the story went, Cross’ bill of rights had not been violated, and thus his public hearing was cancelled. Cross knew the sheriff’s sham charges would be exposed if there was a hearing. Daniels got what he wanted—to be rid of his former campaign manager—but Cross had also accomplished something. He kept his rank, which would benefit him in retirement.

“I’m good,” he said. “I’m not rich, but I made some good financial decisions. I get to spend time with my wife, my kids and my granddaughter.” He said he understands he was hired because of politics and was removed because of politics. He accepts it.

As for Daniels, he is currently under FDLE investigation for alleged violations, but the department seems to be slow-walking through the sheriff’s self-made quagmire. Daniels told friends he would “skate” through and seek another term. Some speculate that since Daniels was a donor and worked in Ron DeSantis’ campaign, the governor won’t touch the issue. If that’s the case, voters will decide Daniels’ fate at the ballot box.

His reelection campaign isn’t raising record funds, however. Former donors told Cross that the campaign has come out of the woodwork asking for donations. They just said “no.” Most of the funds have come from CCSO officers who were told they were “expected to contribute to the sheriff’s campaign.”
Recently, in a bizarre twist, one of Daniels’ command officers contacted him and asked him to come back to work for the campaign. The message: “No hard feeling.”

Like Daniels’ erstwhile donors, Cross just said “no.”

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