Nate Monroe: Reggie Gaffney wants a political dynasty. To get it, he'll have to outrun years of scandal

COMMENTARY | Not for the first time or the last, everyone held their breath: it was Reggie Gaffney's turn to vote.

In May 2016, Gaffney, a Democrat, had publicly pledged his support to Republican Doyle Carter to become vice president of the Jacksonville City Council. Those internal contests matter little to most voters but carry enormous importance among the 19 council members, who often view the vice presidency and presidency as capstones to their modest careers in elected office.

Among the council's quirky and informal rules of etiquette, few are more sacred than a verbal pledge to support a colleague for council leadership. And Carter was counting on Gaffney to make good on his commitment because the vice presidency race that year was going to be unusually close; Gaffney was likely to be the decisive vote.

But the intentions of Reginald Leon Gaffney are always a mystery.

Gaffney, a Republican-turned-Democrat who for years said he attended the ultra-conservative First Baptist Church in Downtown, is a member of one of Jacksonville's most well-known political and sports families. And were he almost any other city politician, Gaffney's career in elected office would have been left for dead long ago, smothered beneath the weight of controversy. That he has survived and thrived in office is due in part to dumb luck, in part to an undeniable talent to raise money, and in no small part because Gaffney is a cipher — he is what you need him to be, in that very moment, until quite suddenly he is not.

What it takes to earn Gaffney's support has been a question of befuddlement, speculation and dark humor among city insiders since his emergence as an eccentric political climber more than a decade ago.

This much is clear: how Gaffney will vote on any particular issue is determined neither by ideology nor by any prior commitment he has made in public or in private — the very reason the smartest lobbyists never factor Gaffney into their vote tallies when wargaming how the council will weigh their clients' interests.

It's a lesson Carter would learn the hard way.

Claiming he had "asked God for guidance," Gaffney switched loyalties in real time and supported Carter's opponent, a pivotal decision that tipped the 9-10 vote against Carter.

Carter would never hold a leadership post during his remaining time on council.

Weeks later, when asked how he felt about Gaffney for a profile my colleagues and I were working on, Carter turned the question back on us: "If you can't trust somebody for their word, then what can you trust?"

It was a quintessential Gaffney moment — distasteful, self-inflicted, inexplicable — and it was a fitting encapsulation of the troubled reputation that has dogged Gaffney throughout his nearly eight years on the Jacksonville City Council. His tenure was clouded by scandals both petty and substantial, including the role federal prosecutors attributed to him and the nonprofit he has run for decades, Community Rehabilitation Center, in ex-U.S. Rep. Corrine Brown's fraud trail. It was also dragged down by a foundational question: Can Gaffney be trusted to do what he says he'll do?

That very question hangs over other members of his family. Gaffney's brother, Johnny, also served on the Jacksonville City Council. During his own tenure, the Democrat did two shocking things: He voted against an ordinance that would have expanded local discrimination protections to the city's LGBTQ community, a crucial vote ensuring its demise (it has since passed); and he endorsed Republican Lenny Curry as he challenged the re-election campaign of former Mayor Alvin Brown, the city's first Black mayor and one Johnny Gaffney had previously supported.

After Curry's victory, the new mayor gave Johnny Gaffney a $92,000 per year job in his administration as the "liaison to boards and commissions," a role with light responsibilities but considerable pay.

Reggie Gaffney's council district includes downtown, granting him a measure of influence over some of the most high-profile and important redevelopment projects in the city. For that reason, and because of his malleable personal politics, Gaffney has been able to count on friends in high places even in his lowest moments.

Republican developers, lobbyists, activists and business leaders — like Jaguars owner Shad Khan — have padded Gaffney's campaign accounts with tens of thousands of dollars over the years, a critical prophylactic that has helped Gaffney weather scandals that might have consumed less wily politicians.

Perhaps emboldened by his nine-lives luck, Gaffney, 63, is eyeing the makings of a political dynasty: Gaffney is running for state Senate District 5 while his son, Reggie Gaffney Jr., is running in a special election to fill his father's seat. Were both campaigns to be successful, it would represent the apex of an infamous family that has had a hand in city politics for decades.

Gaffney loses friends

The Senate district covers most of Jacksonville inside I-295 and Westside neighborhoods extending to the First Coast Expressway — a 500,000-population district that amounts to a major promotion for the neighborhood council member.

For the first time in his elected career, however, Gaffney is facing serious headwinds.

He is competing against state Rep. Tracie Davis in the Democratic primary, pitting him against a formidable, well-liked elected official.

Worse still, the city's right-of-center business establishment has abandoned Gaffney and backed Davis despite her dyed-in-the-wool Democratic bona fides. The JAX Chamber's political committee, JAXBIZ, recently voted to endorse Davis over Gaffney, a stinging rejection for a council member who has eagerly courted developers and distanced himself from the city's Democratic constituencies.

Backing Gaffney's bid came with a "reputational risk" for Jacksonville, someone in the room during the JAXBIZ's secret deliberations told me.

"Whose character best represents the city?" the person asked rhetorically.

Now that he's seeking a larger stage in Tallahassee, the chamber vote signaled that at least some business leaders were taking a less myopic view of Gaffney — a useful politician for them at times — and have also grown weary of his stunningly brazen transactional politics. Gaffney's interactions with donors are the stuff of legend.

In fact, Gaffney's eagerness to court developers has sometimes — and remarkably — managed to anger both residents and the business community. He recently introduced legislation on behalf of a company that wanted to construct a storage building on the downtown Southbank, an idea that so widely panned Gaffney said the outcry "put him on the fence" about his own bill. He eventually withdrew it.

Sloppy, seedy legacy

A penchant for sloppiness and unprofessionalism pervades nearly every enterprise Gaffney touches. To wit: the website for his state Senate campaign erroneously says he's running for District 6 (he is running for District 5). His early campaign finance reports simply didn't list the names of a few contributors who had given him thousands (his campaign said it was an oversight).

This trend extends to more serious issues and has left Gaffney so scandal-plagued he once, in an interview for a lengthy profile my colleagues and I had written about him several years ago, appealed to a higher power in real time. "Why, God? Why me?" he said. "I've never stolen anything from nobody. All I try to do is help folks."

An exhaustive accounting of the problems and controversies that have accumulated during Gaffney's time in the public eye would be impractical to list, but even a sampling is dizzying:

• In December 2015, the Times-Union found Gaffney had avoided paying thousands in property taxes by illegally claiming homestead exemptions on two homes. Gaffney said he forgot that he had an exemption on his old house, which he bought in 1993, when he added an exemption to his new home, which he bought in 2008. Gaffney cut an $11,980 check to resolve the problem the same day the property appraiser notified him of the issue.

• That same year, Gaffney was one of at least seven council members who accepted passes to the watch the Jaguars play from team owner Shad Khan's suite while the team was seeking millions in public financing to construct the future Daily's Place amphitheater and other stadium improvements. Packages sent to council members included two Tiffany champagne flutes. The city's ethics watchdog, Carla Miller, found the council members may have been misled to accept a gift far greater than Florida's ethics law allows.

• Gaffney was among the council members sued by a citizens' watchdog group for violating the Sunshine Law after a Times-Union investigation found he had exchanged text messages with the president of the local firefighters' union over a $300,000 line item to prevent demotions in the fire department. Gaffney settled the lawsuit.

• Federal prosecutors in 2016 subpoenaed numerous records from the nonprofit Gaffney founded 30 years ago and still runs today, Community Rehabilitation Center, in the runup to Brown's federal trial on fraud and tax crimes the following year. Neither CRC nor Gaffney were ever accused of wrongdoing, but the federal government presented evidence Gaffney and his groups were a source of cash for the former congresswoman.

Both prosecutors and Brown listed Gaffney as a potential witness, but neither side ended up calling him to the stand.

• The federal subpoena and his role in Brown's trial also rehashed Gaffney's own rise in city politics. He was known for years as a loyal Brown toady, and in turn Brown acted as a patron saint for Gaffney's nonprofit, CRC, helping it land federal money. In an interview several years ago, Gaffney acknowledged to us that he has used his nonprofit's clients to put up campaign signs and pass out flyers.

• Gaffney and CRC have a long, complicated history dating back to the 1990s. He founded the small nonprofit to help people with mental illnesses and drug addictions, but his group — which relies on money from Medicaid and other public sources — has had difficulty escaping scrutiny. In the mid-1990s, state officials were concerned about nepotism in CRC's hiring practices.

In 2002, prosecutors prepared to charge CRC with Medicaid provider fraud, according to court records, but the state attorney ultimately allowed Gaffney to settle the case with a $55,000 payment (CRC denied wrongdoing in the settlement agreement).

Years later, the state allowed CRC to settle allegations of overbilling Medicaid with a six-figure payment after Jacksonville's two state senators intervened on Gaffney's behalf with state officials.

• Last year, Gaffney's nonprofit was among several run by City Council members that landed large payouts from City Hall — in his case a $500,000 payment to purportedly help his nonprofit recover from pandemic-related economic suffering. None of those nonprofits had to compete for the grant money, which is standard. Instead, the City Council itself signed off on the money with virtually no discussion or questions.

Gaffney a chameleon

The former Republican has never championed Democratic causes, but, facing a formidable and credible Democratic opponent in his state Senate primary, Gaffney has accurately sensed the need to undergo a new metamorphosis: from establishment lackey to liberal lion.

And he has not shied away from using his official position in city government to advance his political interests.

In May, Gaffney filed legislation that would have paid up to $4,000 in travel costs for city employees obtaining abortions in other states. He set the legislation on a fast-tracked, emergency cycle.

It was so wildly out of character and so nakedly performative that Gaffney could barely conceal his own cynicism. "I don't support abortion so you all need to understand that," he said of his own bill. "But what I did support was women's rights."

Remember: Gaffney is who you want him to be — until he's ready to move on.

Gaffney voted to withdraw the bill the following month.

Nate Monroe is a metro columnist whose work regularly appears every Thursday and Sunday. Follow him on Twitter @NateMonroeTU.

This article originally appeared on Florida Times-Union: Can Reggie Gaffney create a Jacksonville political dynasty? | Nate Monroe