DeSantis prevailed over Andrew Warren. Other lawsuits show what might come next

We run through DeSantis’ legal history, including Stop WOKE, “sanctuary cities” and other major cases.
Ron DeSantis announces the removal of Hillsborough County State Attorney Andrew Warren during a news conference Thursday at the Hillsborough County Sheriff's Office administration building in Tampa.
Ron DeSantis announces the removal of Hillsborough County State Attorney Andrew Warren during a news conference Thursday at the Hillsborough County Sheriff's Office administration building in Tampa. [ DOUGLAS R. CLIFFORD | Tampa Bay Times ]
Published Jan. 20|Updated Jan. 20

Even though a federal judge took Gov. Ron DeSantis to task for his handling of Hillsborough State Attorney Andrew Warren’s suspension, the governor ultimately won. Warren, who sued to get his job back, remains out of office.

The victory at the trial court level was somewhat of a rarity for DeSantis, who has sustained many rulings against his priorities during a first term that drew a dizzying number of lawsuits.

The lawsuits hint at an executive who is comfortable drawing headlines for pushing the legal envelope, sometimes challenging precedents unfavorable to his agenda so they can be reversed by either the state or U.S. supreme courts, both of which have recently tilted more conservative.

The Tampa Bay Times analyzed court cases around 15 of DeSantis’ other major policy priorities. Of those, eight were dealt setbacks by trial judges, and a ninth was struck down in an appeals court.

Trial courts ruled in favor of two major DeSantis priorities; the rest are in their early stages.

If Warren does appeal, past rulings in many of these lawsuits don’t favor a reversal. DeSantis has typically fared best in the appeals courts, where many of the judges were appointed by Republicans. Appellate judges reversed unfavorable trial court decisions on four priorities.

This mixed record — having major policies blocked at one level of the courts only to have some of those decisions reversed — has become part of the steady drumbeat of DeSantis’ tenure.

“We typically set our clocks to getting a partisan outcome in that court,” he said in reference to a ruling against a state voting law by Barack Obama appointee Judge Mark Walker, one of the judges who have issued repeated, stinging orders against moves by the governor and Republican-controlled Legislature. “The only question is how quickly (Walker’s decision) gets reversed on appeal.”

Either way, some observers say the way DeSantis messages his legal battles has made it so he comes out on top, regardless of the outcome.

“Most litigants want to win (their cases) ... but for DeSantis, it’s all about winning the news cycle,” said Bob Jarvis, a law professor at Nova Southeastern University in Broward County.

He pointed to the months or years it takes to fully resolve each lawsuit as working in favor of the governor, because by the time a case is decided, the public has often moved on. “The news cycle is so short, and all you want to do is be able to say, ‘I’m owning the libs.’”

Emails that became part of court records during the trial over Warren’s ouster revealed DeSantis’ communications staff privately celebrated that Warren’s suspension garnered more than $2 million in “totally free earned media,” a political term for organic news coverage.

April Schiff, a Tampa Republican political consultant who represents Hillsborough County in the state party, said lawsuits have become part of political life in a highly divided time.

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Schiff disagreed that DeSantis is out to solely win the messaging war, but rather is working to win cases and reverse precedents that have impeded Republican priorities.

“It’s smart,” she said. “He lays out a pathway to say, ‘This is what we’re going to do. ... We can challenge that and set a new precedent.”

A Times/Herald estimate found Florida taxpayers have paid at least $16.7 million to outside law firms defending the state. In one case, a law firm is charging taxpayers up to $725 an hour. It’s unclear exactly how much the lawsuits have cost the state in total.

Related: These law firms have been paid at least $16.7 million to defend DeSantis’ culture wars

When asked about the total cost of the cases, a spokesperson for the governor wrote in an email that the question should be directed to the groups bringing the lawsuits.

“They can’t win at the ballot box, so they turn to the courts seeking to enact their agenda by judicial fiat,” wrote Bryan Griffin, the governor’s spokesperson. “We will not allow the will of Floridians as reflected in the laws enacted by their representatives to be thwarted by activist litigation.”

Here is a recap of some of the most newsworthy cases of DeSantis’ tenure, and where they stand:

Major losses

“Anti-riot” law: Following the 2020 summer of protests against the police murder of George Floyd, DeSantis prioritized a bill that, among other things, enhanced criminal penalties for protests that turn violent or into a riot. He went on Hannity, the Fox News show, a few days before he signed the bill to tout it as “the most comprehensive piece of law-and-order legislation I’ve seen.”

But enforcement of that law by DeSantis and several other officials was blocked in September 2021 by Walker, the federal judge who has often ruled against DeSantis. In Walker’s decision, he argued the new law’s definition of a riot was vague “to the point of unconstitutionality,” and therefore “encourages arbitrary and discriminatory enforcement.”

The state has appealed, but the appeals court hasn’t issued a final decision. Last week, it released an opinion asking the Florida Supreme Court to interpret the way the new law defines the word “riot” to help it come to a conclusion.

The Stop WOKE Act: DeSantis made fighting what he calls “critical race theory” in schools and the workplace a key part of his first-term policy agenda. A 2022 bill passed by the Legislature to crack down on certain types of instruction and corporate training faced multiple lawsuits from both the private sector and educators.

Walker has issued two preliminary injunctions stopping the state from enforcing portions related to workplace training and higher education. Walker in his decisions included sharp rebukes of the law.

In his order related to higher education, he wrote that the state’s lawyers were arguing that professors only had academic freedom if they expressed the viewpoint of the state.

“This is positively dystopian,” Walker wrote.

Related: Judge stops enforcement of Stop WOKE Act at Florida colleges, universities

Florida has appealed both of those decisions.

A battle over “sanctuary cities”: One of DeSantis’ key policy priorities from the 2019 session banned “sanctuary cities” in Florida. But major parts of the law are not being enforced because of a 2021 ruling from a federal judge.

The law was an attempt by the DeSantis administration to crack down on cities that refused to comply with some federal immigration actions, though a Senate bill analysis was unclear on whether any such cities existed at the time they passed the bill. U.S. District Judge Beth Bloom, another Obama appointee, ruled major parts of the law were not constitutional and could not be enforced. However, she did not strike down a requirement that state and local law enforcement hold defendants beyond the date they’re to be released if necessary so federal agents can detain them.

The state is appealing the ruling before the U.S. Court of Appeals for the Eleventh Circuit.

As it makes its way through the courts, DeSantis has continued to tout this law, including during an interview with Fox News’ Tucker Carlson on the eve of the 2022 election.

Gaming deal: A landmark gaming agreement negotiated by DeSantis and the Seminole Tribe of Florida, which was approved by the Legislature and the federal government, was struck down last year by a federal judge in the District of Columbia.

The judge, a Trump appointee, ruled that the compact violated federal Indian gaming law and invalidated the entire agreement, putting a stop to all sports betting and gambling expansion in Florida indefinitely.

The agreement, which DeSantis touted as “more expansive than any other gaming compact in U.S. history,” was expected to generate at least $2.5 billion in revenue for the state in the first five years via payments from the Seminoles. In exchange, the tribe would have had control over sports betting in the state and been allowed to add roulette and craps to their casino operations.

U.S. Secretary of the Interior Deb Haaland has appealed. In a recent hearing, the feds encouraged an appeals court to overturn the ruling.

Victories on appeal

Florida’s 15-week abortion ban: A ban on most abortions after 15 weeks — a key plank of DeSantis’ 2022 legislative agenda — posed a direct challenge to state case law. For more than three decades, state courts have forbidden most abortion restrictions because of the privacy clause in the state Constitution. The DeSantis administration has said it will “ask the Florida Supreme Court to reverse its existing precedent” so that more abortion restrictions can be passed.

A trial court issued an injunction barring the enforcement of the new law in early July, on the eve of it going into effect. However, the law went into effect when the state appealed.

In July, an appeals court panel comprised of Republican appointees declined to reimpose the injunction, writing the plaintiffs had not demonstrated “irreparable harm” to pregnant people’s constitutional rights.

The case is now before the Florida Supreme Court, and DeSantis has said he is optimistic.

Redistricting: In a move that dramatically bucked precedent, DeSantis’ office drew its own version of Florida’s congressional maps during the redistricting process in the hopes of changing existing legal precedent. DeSantis’ version more aggressively favored Republicans than the ones passed by the Legislature — so he vetoed their map, and lawmakers then adopted his. Lawsuits soon followed.

In May, a Leon County Circuit Court judge who was appointed by DeSantis found the governor’s map unconstitutional, pointing to the way the maps dispersed Black voters in North Florida, diluting their ability to elect a member of Congress of their choice.

But just a few days later, a Tallahassee-based appeals court signaled that it did not agree, saying there is a “high likelihood” the previous temporary injunction was “unlawful” — allowing DeSantis’ map to remain in place. The Florida Supreme Court then declined to wade into the fight before the election.

That meant DeSantis’ map was in place for the 2022 election, and had real effects on which candidates decided to run and in some cases likely impacted who prevailed.

Related: Did DeSantis’ map deliver the U.S. House to Republicans? It’s complicated.

The case is ongoing. The final decision is likely to be made by either the state’s highest court or the U.S. Supreme Court.

Voting law: A federal appeals court panel reinstated a Florida voting law last year after Judge Walker struck down major portions of it, saying the law was unconstitutional and discriminatory.

The 2021 law, known as Senate Bill 90, imposes limits on the use of ballot drop boxes, “line warming” activities at polling sites and third-party voter registration efforts. (DeSantis railed against drop boxes while pushing for election reform legislation ahead of the 2021 legislative session.)

Republican leaders who pushed the bill said it was needed to prevent voter fraud. The initial decision of the appeals court at the 11th Circuit allowed the law to be in place for the 2022 election, in part because the court said Walker’s ruling in March was too close to the election.

The 11th Circuit has not yet issued a final decision.

School mask/COVID reopening fights: In the summer of 2020, the statewide teachers’ union plus a few teachers and parents sued the DeSantis administration over an order requiring schools to reopen and offer in-person instruction.

An elected Leon County Circuit judge ruled in favor of the union, saying the state had overstepped. But a few months later, a panel of judges at the 1st District Court of Appeals — judges appointed by Charlie Crist and Rick Scott — threw out the previous injunction and sided with the state. By that point, all the school districts in the state had resumed in-person classes, anyway.

In a separate 2021 lawsuit, parents from around the state challenged a DeSantis executive order barring schools from having universal mask mandates, which also threatened to withhold funding from districts that disobeyed. A different elected Leon County judge sided with the parents, saying the DeSantis administration acted “without legal authority.” But at the appellate level, the judges ruled DeSantis’ order could stand.

About a month later, DeSantis called for a special session, during which lawmakers passed a law barring school districts from requiring masks. The appellate court then said the lawsuit was moot. DeSantis made these fights over schooling into central planks of his 2022 reelection campaign.

A major appellate loss

Big Tech bill: The case surrounding a DeSantis-priority law that aimed to crack down on social media companies like Facebook and Twitter has proven to be one of the biggest exceptions to the pattern of Republicans getting more favorable outcomes at the appellate level.

A three-judge panel at the Atlanta-based 11th U.S. Circuit Court of Appeals found that the 2021 Florida law was unconstitutional, siding with a lower federal judge. The opinion concluding that the Florida government had exceeded its authority was authored by a Trump appointee.

“We hold that it is substantially likely that social media companies — even the biggest ones — are private actors whose rights the First Amendment protects,” wrote U.S. Circuit Judge Kevin Newsom.

In pushing for the bill, DeSantis has argued that the social media companies discriminate against conservatives by censoring their speech. The plaintiffs are industry groups representing tech and communications companies.

The case is now headed to the U.S. Supreme Court. The highest court in the land has not yet said whether it will take the case.

Other wins

Reedy Creek: A lawsuit filed by Orlando-area residents opposing a DeSantis-pushed measure dissolving Disney’s special taxing district was quickly dismissed by a federal judge last year.

The federal judge wrote that the plaintiffs did not have legal standing to sue, in part because the law doesn’t take effect until July 2023. Some legal experts have opined that the law may have violated Disney’s First Amendment rights, since it was passed in response to Disney’s opposition to the Parental Rights in Education law, called the “don’t say gay” law by critics. However, Disney has not sued the state over this issue.

Lawmakers are currently in talks to pass follow-up legislation to tackle some of the many unsettled questions and loose ends left by the bill to repeal the special district.

COVID cruises: The coronavirus pandemic was a time of constant lawsuits, creating a web of sometimes-contradictory opinions as novel scientific and legal questions were debated in courtrooms across America. But in this period of confusion, the DeSantis administration — which opposed vaccine requirements and pushed for the cruise industry to get back to business — generally prevailed in court.

There were two major cases. In one, the state of Florida sued the federal government in April 2021 over the rules the Centers for Disease Control and Prevention imposed on the cruise industry, arguing they unfairly hampered a huge segment of Florida’s economy. The federal judge in that case, an appointee of George H. W. Bush, ruled in favor of the state.

The appeals court at the 11th Circuit, a mix of Democratic and Republican appointees, sided with the CDC — before quickly reversing itself and actually siding with DeSantis. The case eventually fizzled after the CDC’s COVID-19 requirements for the cruise industry expired.

In the second and later case, Norwegian Cruise Line Holdings sued the state of Florida in the summer of 2021 over its new law prohibiting companies from requiring proof of COVID-19 vaccination from its customers, which Republicans called “vaccine passports.” A federal judge appointed by Obama agreed with the cruise company and blocked the state law in August 2021. Just this past October, the 11th Circuit ruled in favor of the state in this case, though by that time, Norwegian had already stopped requiring customers to show proof of vaccination.

High-profile cases in their early stages

Migrant flights: There are at least three lawsuits related to DeSantis’ highly publicized chartered flights of mostly Venezuelan migrants from Texas to Martha’s Vineyard, including one seeking to pry public records from the administration that show how the flights were coordinated.

The federal class action suit filed by several migrants and an immigrant advocacy organization is still in progress. The plaintiffs recently added two top DeSantis aides to the list of defendants.

A separate suit filed by Democratic state Sen. Jason Pizzo seeking to stop state money from funding more flights also is proceeding after a Leon County Circuit Court judge declined to dismiss it. The trial is scheduled to begin Jan. 30.

A lawsuit over the records, filed by the pro-transparency group the Florida Center for Government Accountability, also is ongoing. That group recently asked a judge to hold the DeSantis administration in contempt of court for failing to turn over certain records that the judge previously ordered to be released.

Parental Rights in Education — a.k.a. “don’t say gay”: A law that bans instruction on gender and sexual orientation in kindergarten through third grade, and limits it for older grades, also has been subject to litigation. (This one wasn’t a major DeSantis priority ahead of the 2022 legislative session, but he has embraced it as core to his brand after months of media attention and protests.)

Plaintiffs, including LGBTQ rights organizations, some teachers, students and parents of Florida schoolchildren, sued the state in federal court in March, arguing that the law violated students’ First Amendment and 14th Amendment rights and “would deny to an entire generation that LGBTQ people exist and have equal dignity.”

In September, federal Judge Winsor ruled in favor of the state’s motion to dismiss the case, writing that the individual plaintiffs hadn’t proved how they are harmed by the law.

The plaintiffs filed an amended complaint in October, just a few weeks later. In late November, numerous state officials filed motions to dismiss that complaint as well.

Transgender athletes in girls’ scholastic sports: DeSantis has consistently railed against transgender athletes participating in female sports. In 2021, he signed a bill essentially banning trans athletes from women’s and girls’ scholastic sports. In 2022, he issued a proclamation declaring a female swimmer from Florida who lost an NCAA championship to a transgender competitor to be the rightful champion.

The same month the 2021 bill was signed, a 13-year-old student in Broward County challenged the legislation in federal court. However, the case was put on hold last February while lawyers awaited the outcome of a different federal case involving a St. Johns County School Board policy. The St. Johns policy restricted a transgender student from using his school’s boys’ bathrooms.

In December, a federal appeals court ruled the bathroom policy could stand. That means the transgender athlete litigation is back in motion. But it’s unclear how it will be resolved.

Felon voting arrests: Although they are criminal cases rather than civil lawsuits, the arrests of 20 felons who were ineligible to vote by DeSantis’ elections security force are another prominent test of the governor’s priorities in the courtroom.

While some felons regained their voting rights through Amendment 4, the measure didn’t apply to people with past murder or felony sex offense convictions. At a news conference touting their arrests, DeSantis accused 20 people with those serious convictions of illegally voting, and most of these cases are still ongoing.

However, the few cases that have been resolved so far have not boded well for the rest.

In two instances, judges tossed out the voter fraud cases, saying the statewide prosecutors didn’t have the authority to bring the charges. In another, prosecutors dropped the charges, while in one other, the accused woman took a plea deal that allowed her to avoid any punishment.

Note: A headline that inaccurately reflected the result of today’s Warren ruling was inadvertently published and seen by an unknown number of readers who found the story through Google. Multiple headlines were written before the ruling was handed down, including accurate ones reflected on the website and social media. This one inaccurate headline should have been removed ahead of time. We apologize for the error.