‘Alligator Alcatraz’ main architect eyes a new project: Trump’s endorsement

TALLAHASSEE, Florida — He said President Donald Trump was wrong on Covid-19. He criticized him on abortion. And he mocked his understanding of transgender issues.

Now, James Uthmeier — Gov. Ron DeSantis’ 2024 campaign manager and handpicked Florida attorney general — is betting his political future on Trump’s forgiveness. And he’s putting forward “Alligator Alcatraz,” the detention center quickly constructed in the Everglades to help the president carry out his mass deportation plans, as his boldest gesture yet.

There are signs it may be working: The president is now praising Florida’s new attorney general for his role as one of the main architects of the detention center.

“The guy’s got a future,” Trump said when he visited the facility this month.

The path forward for the 37-year-old Republican — whom DeSantis has called a “bulldog” — now may hinge on whether he can turn accolades from Trump into an endorsement for 2026, mitigating his past criticism of the president and his alliance with the governor.

POLITICO interviewed more than a dozen Republican operatives, consultants and fixtures in Florida’s political scene about Uthmeier. They detailed his efforts to secure a potential endorsement from Trump, with whom an Uthmeier spokesperson said he has “great working relationships,” and win support from other GOP politicians who don’t have a close connection with DeSantis.

“James said some bad things about President Trump when he was running the DeSantis campaign,” said former Rep. Matt Gaetz, a Trump ally who at one point was seen as a potential rival for the state attorney general job. (He now says he has no plans to seek office next year.)

“I’m sure that looms larger than I do,” Gaetz added of Uthmeier’s past remarks.

DeSantis appointed his former chief of staff to the post of state attorney general this past February after the governor elevated Ashley Moody to the U.S. Senate to fill Marco Rubio’s old seat. Uthmeier is already raising money to run for a full four-year term next year.

DeSantis’ decision to appoint Uthmeier to fill the post until the next election was seen as a reward for Uthmeier’s work for the governor that started during the pandemic and included attention-grabbing moments, such as helping organize the flights carrying migrants from Texas to Martha’s Vineyard. Uthmeier also helped shape the governor’s image, suggesting that DeSantis begin showing more of his personal side on social media that included posting football prediction videos with his son, said one GOP lobbyist granted anonymity to relay behind-the-scenes dynamics.

“All throughout our administration James was always digging in and fighting for what was right even when it was not easy,” DeSantis said at Uthmeier’s swearing-in ceremony in February. “There wasn’t anything that happened in our administration that James was not involved in.”

In just a few years, Uthmeier went from general counsel to chief of staff then campaign manager in the final months of DeSantis’ ill-fated run for president. After returning to his chief of staff post in early 2024, Uthmeier then assisted the governor’s successful campaigns against two ballot initiatives dealing with abortion and marijuana access.

‘Working overtime courting everyone’

Uthmeier, a native of Destin who once contemplated running for Congress, has never run for office before. When he was first appointed state attorney general, there was plenty of speculation about other Florida Republicans prepared to challenge him — possibly with the backing of Trump.

“I’ve been told James is very much on the bad list,” one Florida Republican operative said earlier this year.

But it’s clear that Uthmeier is already trying to smooth his path to the Republican nomination next year. And a Trump endorsement would be widely viewed as further chilling any competition for the August 2026 primary.

This past spring, for example, Uthmeier, a graduate of the University of Florida, attended a Gators basketball game with state Sen. Joe Gruters of Sarasota, a longtime Trump ally who has clashed with DeSantis.

“The attorney general has been working overtime courting everyone,” said Max Goodman, a Republican consultant and longtime adviser to Gruters. “He understands the significance of a Trump endorsement and whether that gets him crossways with the governor is a risk he’s clearly willing to take.”

Other Uthmeier backers have strong connections to both Trump and DeSantis. U.S. Middle East envoy Steve Witkoff, for example, is among those who have bent the president’s ear about Uthmeier and how committed he is to his agenda, according to four lobbyists and GOP consultants granted anonymity to relay private conversations.

“Witkoff and James worked together to bring the president and governor together after the election,” said one Florida Republican lobbyist. “That relationship has flourished ever since.”

During a brief one-on-one following Trump’s roundtable at Alligator Alcatraz, Uthmeier told Trump, “I’ve got your back,” according to a person familiar with the conversation granted anonymity to detail a private conversation. The comment is notable, as NBC News previously reported that some in the Trump administration were upset DeSantis did a walk-through of the site with "Fox & Friends" days before Trump’s visit. Three people familiar with the situation confirmed this did create “tension” because the White House wanted it to remain unseen until federal officials were there in person.

Asked about the interaction, a White House official responded that Trump was “grateful to work with [Homeland Security] Secretary Noem and local officials on this important project to get dangerous criminals out of American communities.”

When asked about the effort to win over Trump, Kayla Little, a spokesperson for Uthmeier’s campaign, did not directly answer the question. Instead, Little pointed to Uthmeier’s previous work for Trump and said, “James maintains great working relationships with the current Trump administration and in his capacity as AG he has worked closely with numerous Trump officials to help deliver on the president’s agenda.”

Angling for the big endorsement

Trump just last week called DeSantis his “friend” despite their 2024 rivalry. But navigating the politics to angle for an endorsement is tricky for Uthmeier, as several GOP insiders say there are still some wounds between Trump’s inner circle and DeSantis.

Another dynamic Uthmeier’s allies are watching is whether he’ll be put in a difficult position to endorse Gruters for state chief financial officer, given not just his DeSantis rivalry, but a key disagreement with the state senator on marijuana legalization. He could also be pressured by state Republicans in the primary to endorse the gubernatorial bid of Rep. Byron Donalds, whom DeSantis has already brushed off as an undeserving potential successor. Little did not respond to a question about who Uthmeier supports for governor or chief financial officer.

But a Trump endorsement is an enviable prize in Florida. DeSantis boosted his own political career with a well-timed Trump endorsement during his initial run for governor. He became a national conservative star due to his response to Covid-19 and battles over race and gender identity. Uthmeier had worked for Commerce Secretary Wilbur Ross during the first Trump administration, then took a job with DeSantis early in his first term.

He became one of DeSantis' most trusted advisers. When the governor’s presidential campaign was floundering, DeSantis turned to Uthmeier during the final stretch.

“He had DeSantis’ full trust,” said one Florida Republican consultant. “After a period of time, they clicked better than any chiefs of staff he had had.”

Another GOP consultant who worked with Uthmeier said one of his priorities was nurturing relationships, something the governor hasn’t been known to do. But there was otherwise a “mind meld” between the two. The governor often brought ideas to his team; Uthmeier was among a small cohort who knew how to shape, execute and market those ideas and bring his own to the table, the person said.

“He just thinks like that: How do we bring things to life, get things done quickly and not get lost in bureaucracy?” the person added, describing Uthmeier as “sincere in his beliefs” and someone who “only works for people he believes in.”

Under the magnifying glass

The work Uthmeier did for DeSantis, however, has also come under scrutiny that could haunt him during his campaign. A probe by state House Republicans delved into how a nonprofit linked to Hope Florida, an initiative spearheaded by first lady Casey DeSantis, received money from a settlement with a Medicaid vendor. The Hope Florida Foundation was able to then steer money into two other groups that within days sent millions to the political committee fighting the marijuana initiative — and led by Uthmeier.

Florida’s attorney general has denied any wrongdoing, but the Republican legislator who led the probe has asserted Uthmeier may have committed fraud. State Rep. Alex Andrade (R-Pensacola) has called it a misuse of taxpayer money and Medicaid funding. One Florida GOP operative called the Hope Florida allegations a “big problem” and a “huge ticking time bomb,” especially if the Legislature plans to revisit it during next year’s session.

Still, several Tallahassee insiders saw Trump’s visit to the “Alligator Alcatraz” immigration detention center as a slam dunk for Uthmeier. The former chief of staff did not join Trump and DeSantis on the tour of the facility. During a roundtable, however, the president praised him and said he’d heard positive things about his record.

“He would not say that if there was a current intent to help someone else,” said one longtime GOP lobbyist.

Jeremy Redfern, a spokesperson for Uthmeier in the attorney general’s office, acknowledged law enforcement officials in the state had brought up the need for detention beds to assist Trump’s deportation efforts, leading to the decision to use the training airport site. Redfern said in an email that “James and state leaders had been considering possible uses of the property for years, and its features presented an ideal location for a one-stop shop illegal immigrant detention center, surrounded by the Everglades.”

The “Alligator Alcatraz” opening — which has drawn criticism from immigration advocates and Democrats and triggered a lawsuit from environmental groups — was Uthmeier’s most high-profile act since becoming attorney general, though others could be seen as overtures to Trump. Uthmeier recently was held in civil contempt of court after using Trumpian language about how the courts have overstepped on the executive branch. He also filed a class action against Target, claiming it defrauded investors by promoting “radical LGBTQ activism.”

In other high-profile instances, he opened an investigation into Andrew Tate and his brother, Tristan, after they faced charges of human trafficking and rape, and called out local governments that refuse to help the administration with federal immigration enforcement. One GOP adviser said that Uthmeier’s actions in his job demonstrate DeSantis made the right choice.

“The governor feels validated by James’ success,” the person said.

Further raising his profile, Uthmeier has done long-form podcast interviews, held press conferences all over the state and showed his punchy style is similar to that of his former boss in the governor’s mansion.

“They were a good combination together,” said Slater Bayliss, co-founder of The Advocacy Partners, who was on the DeSantis’ presidential campaign finance advisory team. “And now you’re seeing James grow on his own.”