Ron DeSantis is campaigning on his record. Judges keep saying its unconstitutional

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Gov. Ron DeSantis has toured the country calling Florida the place “where woke goes to die.” But it’s still alive at the company Sara Margulis runs.

At Honeyfund, a website for engaged couples to create gift registries that can pay for their honeymoons, Margulis’ Florida employees learn about privilege and institutional racism. Margulis, the CEO and co-founder, said the training makes her staff better suited to serve couples of any background. Planning for this fall’s employee retreat is underway, with a session scheduled on DEI – or diversity, equity and inclusion, a term DeSantis often rails against.

DeSantis tried to ban such employee training in 2022, when the Florida Republican championed what he called the Stop WOKE Act. But Honeyfund and others sued on the grounds that the law violated their free speech. A federal judge agreed and blocked it from going into effect. The DeSantis administration then appealed – one of many of the governor’s ongoing legal battles as he pursues the presidency.

“Companies aren’t ‘going woke’ out of allegiance to Democrats. Time after time, diversity has proven to be good for the bottom line,” Margulis said. “Valuing diversity means understanding it, understanding means training and training means having to deal with this law. We were really handed a chance to make a difference for other business owners by challenging it, and we took it.”

In his early outreach to Republican voters as a presidential candidate, DeSantis has portrayed himself as a fighter and, crucially, a winner in the cultural battles increasingly important to conservatives. If elected to the White House, he’ll take those fights to Washington, he has said.

“I will go on offense,” DeSantis said in Iowa last month. “I will lean into all the issues that matter.”

But back in Florida, the agenda at the centerpiece of his pitch remains unsettled. Still ongoing are more than a dozen legal battles testing the constitutionality of many of the victories DeSantis has touted on the campaign trail. Critics say DeSantis has built his governorship around enacting laws that appeal to his conservative base but that, as a Harvard-trained lawyer, he knows are unconstitutional and not likely to take effect.

In addition to halting parts of the Stop WOKE Act, judges have also intervened to freeze implementation of other DeSantis-led laws cracking down on protesters and Big Tech. The six-week abortion ban he signed this year – which he has called the “heartbeat bill” when speaking to conservative, and especially evangelical, audiences – won’t take effect unless the state Supreme Court determines that a privacy clause in Florida’s constitution doesn’t protect access to the procedure. Disney – the most famous of DeSantis’ political adversaries – has argued in court that the governor overstepped his power when he orchestrated a takeover of the entertainment giant’s special taxing district to punish the company for speaking out against his agenda. So did Andrew Warren, the twice-elected Tampa prosecutor whom DeSantis suspended last year in another act of political retaliation.

DeSantis has repeatedly predicted he will ultimately prevail in these challenges. Bryan Griffin, a spokesman for his campaign, called the lawsuits “the tactics of activists who seek to impose their will on people by judicial fiat.”

“These attempts to circumvent the will of the legislature are not indicative of anything beyond the failure of the left’s ideas at the ballot box,” Griffin said in a statement. “Governor DeSantis is a proven fighter who will bring the same temerity to the presidency.”

Recent weeks, though, have seen a handful of reminders that several pillars of his record remain fragile even as they figure prominently in his stump speeches.

On Friday, a federal judge blocked a new Florida law that gave the DeSantis administration the power to shut down bars or restaurants that admit children to certain “adult live performances,” widely seen as a crackdown on drag shows.

Another federal judge said Wednesday that Florida could not restrict transgender adults on Medicaid from receiving gender-affirming care. The same judge earlier this month had stepped in to allow three transgender children to receive puberty blockers while a lawsuit seeking to overturn a state ban on the treatment proceeds. In both rulings, the judge said there was “no rational basis” to prevent the care and declared “gender identity is real,” casting doubts on the future of the state’s prohibition.

DeSantis, as a presidential candidate, has seized on conservative concerns over such treatment, particularly for minors. His efforts to halt it – including signing a law that prohibits transgender children from receiving gender-affirming treatments and punish doctors who run afoul of it – are prominently featured in his stump speeches. Speaking to North Carolina Republicans after the ruling, the governor acknowledged the legal fight, but he assured the audience: “We are going to win.”

“It is mutilation, and it is wrong, and it has no place in our state,” he said.

DeSantis of late has also taken credit for the GOP’s narrow US House majority, noting the highly partisan map he pushed through his state legislature, which ultimately helped Republicans net four critical seats. But those suing Florida to invalidate the state’s congressional boundaries have new reason for optimism after the US Supreme Court ordered Alabama officials to redraw its map to allow an additional Black-majority district. The DeSantis map was similarly criticized as diminishing the power of minority voters in Florida.

“Many of the things coming from the governor are form over function,” said Cecile Scoon, president of the League of Women Voters of Florida, one of plaintiffs in the redistricting lawsuit. “They want to get to a certain result, so they find a means to do it, whether it makes logic or legal sense or not.”

The US District Court for the Northern District of Florida has in particular stymied DeSantis’ agenda. Two judges on the bench, Mark Walker and Robert Hinkle, have repeatedly ruled against the governor, often punctuating their opinions with harsh and colorful repudiations.

Walker, in one ruling blocking parts of the Stop WOKE Act, compared Florida’s treatment of the First Amendment under DeSantis to the “Upside Down,” the nightmare alternative dimension from the Netflix series “Stranger Things.” In another lawsuit over the law, this one filed by college professors, Walker called the law “dystopian” and wrote that DeSantis and Florida Republicans had “declared the state has unfettered authority to muzzle its professors in the name of ‘freedom.’”

Hinkle, in January, chided DeSantis’ suspension of Warren as political, unconstitutional and executed with “not a hint of misconduct,” though he ultimately ruled he was powerless to intervene. Warren is appealing, though he suffered another defeat when the state Supreme Court on Thursday rejected a separate request to reinstate him.

Ruling this month against the state in the two cases dealing with transgender care prohibition, Hinkle called the law “an exercise in politics, not good medicine.”

“Nothing could have motivated this remarkable intrusion into parental prerogatives other than opposition to transgender status itself,” he wrote.

DeSantis has shrugged off these defeats as the work of left-leaning judges. President Barack Obama nominated Walker to his district court judgeship in 2012, and Hinkle was selected by President Bill Clinton in 1996. Neither nomination drew objection from Senate Republicans at the time.

When Walker ruled to block Florida’s anti-riot law – comparing it to past attempts to squash dissent from Civil Rights activists in the 1950s and 60s – DeSantis dismissed it as “a foreordained conclusion in front of that court.”

“We will win that on appeal,” DeSantis said. “I guarantee we’ll win that on appeal.”

That assurance came 21 months ago. In the meantime, the law has yet to take effect.

Dana Thompson Dorsey, a professor of education law, was among seven Florida college professors who sued to block the Stop WOKE Act over provisions that limited how she and her colleagues could talk about race and sex with students. She called Walker’s decision halting the law a “work of art.”

Since then, she has continued to teach critical race studies to her doctoral students at the University of South Florida, while DeSantis has taken his fight against the concept national. But despite winning injunctive relief, she remains troubled by the new environment for higher education under DeSantis.

“There is a lot at stake and it’s not just for those of us brave enough to be plaintiffs,” she said. “The idea of telling adults what they can and cannot learn is unfathomable. The students who become our future leaders will repeat our mistakes if they don’t understand the past.”

While legal challenges have prevented DeSantis from fully realizing his vision for Florida, the uncertainty has not always benefited opponents and the plaintiffs suing to block his agenda.

Abortions after 15 weeks have paused in most cases in Florida while providers await a ruling on the state’s ban. Andrew Warren remains out of office. Transgender care providers are in uncertain territory – Hinkle’s limited rulings provided relief but only for those who sued the state.

The League of Women Voters of Florida is taking the state to court over new restrictions on third-party voter registration. Fines for violating the law could cost as much as $250,000 a year and the organization has asked for a preliminary injunction to prevent its enforcement. In the meantime, the league decided it would no longer collect and turn in voter registration forms, pausing for now a practice that has been central to its civic outreach for more than 75 years.

“That’s a very sad and horrible result, but we cannot figure out a way to protect ourselves without that major change,” Scoon said.

DeSantis has also managed to maneuver when legal challenges have threatened to stymie his efforts, thanks to a closely aligned Republican-led legislature.

When a lawsuit accused the governor of breaking state law when he sent two planes carrying migrants from San Antonio, Texas, to Martha’s Vineyard, Massachusetts, lawmakers helped change the law to allow him to do so. His administration recently orchestrated the transport of migrants from El Paso, Texas, to California.

After several individuals arrested last year for voter fraud by DeSantis’ new election security force had their cases dismissed, lawmakers again tweaked the law to try to make it easier for the state to secure convictions.

DeSantis and Florida Republicans have signaled they intend to keep fighting in court, too. The budget DeSantis signed earlier this month included $16 million for legal battles underway and the ones to come.

“We will never surrender to the woke mob,” the governor recently told an audience in Greenville, South Carolina. “We are going to leave woke ideology in the dustbin of history where it belongs.”

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