Nate Monroe: Will Mayor Lenny Curry's legacy ever escape the shadow of scandal?

I. A builder, humbled

It had been several years since I’d walked into City Hall to interview the mayor of Jacksonville, and in the strictest sense that remains the case: On a stifling late-June afternoon I walked through the metal detectors and passed beneath the grand atrium not to talk to Lenny Curry, the man who, for a few more days, at least, still retained the powers and duties of mayor, but rather to interview the remarkable woman who would replace him, Donna Deegan.

It turns out Curry didn’t want to talk to the Times-Union in his final days. There wasn’t much drama in it, just a characteristic shrug from his press office — a final chance to spurn the newspaper Curry believes to be at least partially responsible for the bad times.

Curry swept into office in 2015 with a healthy disdain for the city’s legacy institutions — its press, its civic leadership, its government agencies. He saw the city as rotted by too much talk and too little action, over-studied, over-taskforced, over-committee’d, and he, an accountant by training, flanked by a duo of fearsome Tallahassee political operatives, was here to do things, to build things. Curry made that his first official motto, slapping it on the political committee he formed after he’d taken office: Build Something that Lasts.

Curry, the former chairman of the Republican Party of Florida with close ties to then-Gov. Rick Scott, had impressed the state’s political world by ousting a popular incumbent, Alvin Brown, the city’s first Black mayor and a rising Democratic star at that time. Curry had also managed to unite a powerful coalition of local political donors and civic leaders, including the city’s most recent mayors, who had grown frustrated with Brown. Many of these backers were not and never would be fully sold on Curry — a slight he’d remember the entirety of his eight years in office — but their support lent his narrow victory over Brown the patina of a mandate.

Curry sought to fortify that mandate by reshaping Jacksonville politics. He became the first mayor to open a standing political committee — not for re-election, just to have a few million dollars on standby — making fundraising more or less a constant of his tenure in office, and he injected raw, nationalized partisanship into local politics. The boundaries between his campaign apparatus and his governing team were always hazy; eventually, they simply became one and the same.

Most importantly, the economy had turned in Curry's favor. Brown faced unusually lean years during which city finances shrank, requiring painful cuts and paltry infrastructure budgets. Curry, by dint of pure luck, would never know that austerity.

And in those early, heady days, Curry was intoxicated. Ever excitable, Curry seemed to genuinely marvel at the trappings of office — free tickets, the security detail, rides on the Jaguars charter plane to away games — a thirst that never ebbed during his eight years in office. Although he often acknowledged the fleeting nature of political capital and his time in office, Curry also said things that left me wondering whether he truly understood he wouldn't be mayor forever and that there had, in fact, been mayors before him. He bristled when others recognized progress made by his predecessors, none more than Brown.

Let's say this: The man did not lack for self-confidence.

Curry was fond of saying, for example, things like, “you won’t recognize downtown when I’m done.” He imagined construction cranes dotting the skyline. After decades of stasis, Curry the builder would show all the nattering cocktail sippers how to fix the downtown puzzle. This was, of course, an incredibly high bar to set for himself.

Eight years hence and back here on Earth, downtown Jacksonville remains utterly recognizable, save for a few more fallow lots than when he’d started. Curry the builder turned out to be Curry the demolition man. Curry the decider turned out to be Curry the ditherer. This was not for a lack of spending. City Hall has poured enormous sums into downtown. Take the site of the former Landing: Curry refused a deal Brown's administration negotiated to help the then-owner, Toney Sleiman, redevelop the copper-topped waterfront mall with a public investment of about $12 million. Instead, Curry bought out Sleiman, demolished the property, and more or less punted on what would replace it.

The result: The city, thus far, has plunked down about $25 million on the property — more than twice the $12 million deal Brown negotiated nearly a decade ago — and it remains a sun-blasted vacant lot. Sleiman, the former owner who backed Brown's re-election, an insult that seemed to drive much of Curry's eagerness to demolish the mall, walked away with a sweet $15 million and then some, thanks to some deft legal maneuvering that cost the city even more over the years. And building an "iconic" park will cost millions and millions more and take years still.

Under the self-assured Curry, the city squandered its most precious resource — time — and so downtown emerged from one of the most prolonged periods of economic prosperity in history with tragically little to show for it. In late 2021, Shad Khan, the owner of the Jacksonville Jaguars who had become one of Curry’s most important political benefactors, declared downtown had “gone downhill” in the decade since he’d owned the team — an unmistakable, though likely unintended, indictment of Curry’s record on downtown revitalization. Curry’s office had no comment at the time, but he has, in recent years, recalibrated his public remarks about the legacy he hoped to leave — no longer the builder but the foundation layer.

His successor, Curry has said, will "cut a lot of ribbons."

Downtown is the most physical manifestation of the ways in which the job has humbled Curry, though it’s far from the only or the most severe.

II. The mayor Twitter delivered

We've rarely had to ask what Curry thought as some of his well-laid plans collapsed throughout his tumultuous eight years because Curry tweeted. And tweeted. And tweeted.

He insulted constituents. He posted videos of himself skateboarding, shared photos of his workout stats and pictures that demonstrated his marginal prowess with a smoker. He had a particular penchant for sharing quotes by Carl von Clausewitz, an oft-quoted 19th century Prussian general, and Marcus Aurelius, a Roman emperor fictionalized in "Gladiator," from which he's also quoted. He bashed this newspaper generally and individual journalists specifically, followed by then, without a hint of irony, touting coverage in said newspaper. He instructed us to “pray the hours," inveighed that “winning solves ALL problems," and showed off napkins he had monogrammed with Jay-Z lyrics for a lavish re-election ball in 2019. He shamelessly gaslighted. He once seemed to imply a member of the City Council was unfaithful to his wife (an exchange that may well have doomed a major redevelopment proposal his administration was whipping votes for). Curry could be cryptic. He sometimes seemed lonely. He could also be deeply vulnerable, particularly in the aftermath of the death of his father in May, and gracious, as he has been toward Deegan, who is set to take office Saturday.

Curry’s administration often came under fire for fostering an air of secrecy around city business, but Curry’s Twitter feed was a remarkably transparent and real-time view into his state of mind, albeit one that many of us often wished we didn’t have. And that leads to an unexpected insight: For better or worse, we’ve collectively come to know Curry better than we’ve known any other Jacksonville mayor. None of his predecessors so publicly shared their inner selves and in turn saw their inner selves so closely scrutinized.

In person, Curry is a bit more introverted, a bit more reflective and all around a lot more likable than the Twitter persona he mostly inhabited — one that was brutish, unapologetic and just plain weird. Yet this was the face he chose so often to put forward and thus the one many of his constituents will remember him by.

III. His greatest weakness

Curry's Twitter habits attracted loads of unflattering coverage, but social media was not responsible for his greatest unraveling. Curry — the co-founder of a professional staffing firm — made chronically poor hiring choices.

He too often valued loyalty over competence and tended to favor younger, less experienced social and political climbers not unlike himself — the kind of people who might self-apply the term "disruptors." Because Curry came into office with a built-in disregard for the city's institutions, he did not believe it required any particularly specialized knowledge to run them. It also meant he did not value nationwide, above-board searches for the most experienced professionals. Instead, Curry-appointed boards moved swiftly to oust their existing leaders and settle on new ones — always locals, and always "friends of the administration" — with flimsy pretexts. In one case, Curry's administration whipped council votes for a rewrite of the required experience spelled out in the city ordinance code so it could elevate a preferred candidate (a friend of the family) to run the city's Office of Sports and Entertainment.

This was a recipe for failure. It stained one of the major efforts of his first term, the creation of the Kids Hope Alliance, which was a merger of two existing agencies that provided and administered city-supported youth programs, and it nearly derailed Curry's second term entirely.

Does it even need to be recounted at this point? JEA and Aaron Zahn, two names Curry will never forget and never live down, the key ingredients behind what a former city general counsel called one of the "greatest schemes to defraud the taxpayers in the history of our city."

Curry's botched effort to privatize JEA — the publicly owned utility that has served Jacksonville for well more than a century — has a legacy that will outlive his time in office and may well overshadow his own. A trial over charges of wire fraud and conspiracy brought by a federal grand jury against Zahn, JEA's former CEO, and Ryan Wannemacher, the former CFO, is scheduled to begin in February.

IV. His greatest passion

In campaign mode, Curry was everywhere, eager to chat, accepted any invitation from a community group, clearly enjoyed himself, worked hard. But in the day-to-day trenches of governing, he proved to be a far more spectral figure — more likely to be found at the Y or play-acting coach at Jaguars OTAs than he was on the 4th floor at 117 W. Duval St.

Curry views the world through the lens of contact sports (one of the most common themes contained within his stream-of-consciousness Twitter feed), and so what interests him in politics is the red-team-vs-blue-team aspect of it, that there has to be a winner and a loser — the competition of it all.

His election and re-election campaigns were not enough to slake this thirst. As mayor, Curry sought out even more campaigns to plunge into. The pension-reform plan he pursued in his first term required a voter referendum; he threw his weight behind an ultimately meaningless referendum over legalizing slot machines in Duval County; when the School Board initiated a referendum to support a half-cent sales tax for a countywide schools renovation and rebuilding plan, Curry formed a campaign supporting it even though he had initially fought the School Board over the plan and schools advocates did not want or need his support; privatizing JEA would have required a voter referendum, had that calamitous process made it that far; and as recently as this year, in the twilight of his second term, Curry was pushing the council to greenlight a non-binding referendum asking voters to change the charter to include a local resign-to-run law (the council killed it).

This was not always a bad thing.

On matters of actual policy, Curry seemed far more indifferent, lending him an ideological flexibility that, perhaps unexpectedly, paved the way for some of his administration's highest-profile successes. And his competitive streak made him a forceful ally. He was highly partisan but not an ideologue.

He flooded a notorious housing complex with city inspectors and, locking arms with a Democratic member of the City Council, effectively used his bully pulpit to clean it up and attract federal attention. He championed an increase in the gas tax to kick off a spree of badly needed infrastructure investment across the city, with an emphasis on some long-underserved areas. He hired a chief resilience officer (after years of ambivalence about climate change). He took down one Confederate monument in James Weldon Johnson Park and unsuccessfully pushed the City Council to remove another from Springfield Park. In the face of an intractable violent crime problem, he showed a willingness to experiment — even if some of those ideas haven't worked out quite as well as intended.

These were the right things to do, things people had begged him to do, and they were decidedly un-Republican things to do. They will likely be some of the longest-lasting and most attractive aspects of his legacy — even though his antics and the scandals he ignited often overshadowed them in real time.

Sometimes, though, his devotion to partisan posturing led him to run away from his better moments in office. During the height of the pandemic, Curry imposed plenty of the so-called lockdown measures Republican politicians now deride, like mask mandates, and elevated the voices of public-health experts in his own messaging. Then, as COVID became a political football, almost as a form of repentance, Curry aggressively bid for Jacksonville to host the Republican National Convention — doing so not just during a public-health emergency but amid a volatile national climate in the wake of the murder of George Floyd at the hands of Minneapolis police officers.

This was illustrative of the frustrating boom-and-bust cycle throughout Curry's administration: He'd do something good or openly acknowledge some error, then in due time either reverse the progress or gaslight. In the long term, there was never growth; the Twitter troll was never locked away for long.

And that is a shame in the truest sense. At his best, Curry displayed a willingness to change his mind, to accept help, and to do things that he understood would harm his political future simply because he believed they were the right things to do. At his worst, he was secretive, partisan, thin-skinned and retaliatory, too devoted to a rigidly top-down administration in which ideas flowed from his friends and from special interests instead of the neighborhoods.

We saw too much of the latter and not enough of the former.

V. His greatest sin

Curry can't be unaware of these things.

It simply can't be lost on Curry that he won office in 2015 by bashing Brown over crime — and, to be more precise, by spinning a misleading narrative about it. Curry grossly exaggerated what was then a small increase in violent crime and slapped Brown with a false accusation he'd cut 147 police from the Jacksonville Sheriff's Office budget, a fictional problem Curry pledged to rectify.

This was Curry's cardinal lie and a Faustian bargain that doomed his administration before he had even been sworn in.

In the end, Curry oversaw some of the worst years of violent crime in the city's modern history, and Brown, it's now clear, presided over some of its least violent. It was incredibly foolish for Curry to have won office this way, by exploiting a complex issue outside the control of any mayor and promising to fix it. Contrary to the cringe-inducing personal motto he's shared incessantly — "winning solves all problems" — winning didn't solve this problem. It remains and is now his successor's burden.

And so judged by that standard, the very standard he held his predecessor to, Curry's two terms must be considered a failure.

Judged by the state of downtown — that it is recognizable, that it would in fact be recognizable to someone who died more than three decades ago — his tenure is a failure, the only possible determination after considering another unfortunate standard he set for himself.

Judged by what he was gifted — a historically robust economy — and what he produced, measured against what all the city's other modern mayors were given and what they produced, does it feel like Curry stands out in a flattering way?

Judged by his true passion — electoral politics — what is the result? The former chairman of the Republican Party of Florida is handing the keys to a Democrat whose campaign was built around the idea that City Hall needs to clean house, a message that attracted thousands of Republican voters to her side.

He is leaving his successor a hulking downtown jail he wanted to move but didn't, a thorny Jaguars stadium negotiation he desperately wanted to finalize but never even began, a bankrupted solid waste fund that will likely require a hike in the trash fee, a potential recruitment and retention problem in JSO and the fire department, courtesy of pensions he wiped away for new hires. He suffered through a lengthy federal investigation of one of the city's largest agencies, JEA, and saw one of his former associates charged with serious crimes.

Perhaps these are incomplete ways of taking a full measure of Curry's eight years. Maybe they overlook some of his wins and ignore nuances that might alter some of these conclusions. They might deny him some measure of good faith, or fail to acknowledge some of his redeeming qualities.

That is precisely the way Lenny Curry would judge a political opponent. He'll have to hope history is kinder.

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: Nate Monroe: Will Mayor Curry's legacy escape the shadow of scandal?