TALLAHASSEE, Fla. — The last time Florida Gov. Ron DeSantis was fighting former President Donald Trump, he had one of the most powerful operatives in Republican politics punching alongside him.
But now, as Trump lines up against DeSantis in a battle over a high-profile ballot initiative to legalize marijuana in Florida, the governor’s old ally, Jeff Roe, is working against him.
The renowned GOP operative, whose reputation is built on a one-stop political firm that brings in tens of millions of dollars each election cycle, once led Never Back Down, a super PAC that backed DeSantis’ presidential primary campaign. Prior to that, Roe helped raise money for DeSantis’ long-shot gubernatorial bid in 2018.
The relationship, however, soured after DeSantis’ presidential ambitions went up in flames. Those close to DeSantis had a falling out with the Roe-led team that ran Never Back Down, with finger-pointing over a presidential campaign that did not go as well as anyone anticipated.
Now, roughly a year after that blowup, Roe is on the verge of potentially getting the 60% voter approval needed to add the legalization of recreational marijuana to the Florida constitution, something DeSantis has forcefully opposed and spent significant sums of money — both political and taxpayer dollars — trying to defeat.
Three Republican operatives who previously worked for pro-DeSantis efforts said the battle has become personal between the two men and their operations, with animosity from the campaign spilling over into this fight.
“To say the feud has gotten personal I think would be a drastic understatement,” one person said. “The initiative itself is very important politically for DeSantis, but there is an added layer of motivation in all of this.”
“It has gotten personal on both sides,” a second person said. “I mean, towards the end [of the presidential campaign], DeSantis’ senior staff and people were going around the state, if not the country, ripping Roe as a guy who misspent their money and not doing right by the governor. So, I think there is an appetite on Roe’s part to want to win and to show the world he is not that guy. And I think you have DeSantis people who, for whatever reason, are really pissed off at Jeff.”
The main group arguing against the amendment and DeSantis’ office declined to comment for this story. Roe declined to comment, too.
DeSantis is spending serious political capital in an effort to stop two amendments from passing this November: one that would legalize recreational marijuana, and another that would enshrine abortion rights in the state. The latter would undo the state’s six-week abortion ban, one of the governor’s most significant legislative accomplishments.
But DeSantis has a fight on his hands.
In June, a Fox News survey found that 66% of Florida voters were for marijuana legalization while just 32% were against it — and that came before Trump said he would support the marijuana initiative. (As for the abortion measure, Trump waffled a bit but finally said in August that he, as a resident of Florida, would vote against it, aligning with DeSantis’ position.)
“It’s tough, it’s an uphill fight there,” a DeSantis ally said of the battle over recreational marijuana. “The other side has a ton of money. Over $100 million. So whenever you’re going against that much money, it’s obviously a tough fight.”
But the involvement of Roe and his firm, Axiom, adds another wrinkle to the fight. Their involvement was first reported last year, while DeSantis was still running for president. And as Axiom officials noted, the firm’s work on the initiative was made clear to DeSantis before Roe ever signed on to lead the super PAC backing his candidacy, as it began its work on the initiative in 2022. It wasn’t seen as a big issue.
“No, it hasn’t been uncomfortable,” an Axiom official said of working against DeSantis on the issue. “We certainly have known where the governor stands on this position since the beginning, and we also know he was very helpful to the industry and helping set up the medical marijuana infrastructure and guidance in the state.”
This person added that DeSantis has been campaigning against the initiative “as if it’s his own name on the ballot.”
“We have President Trump’s support on this ballot initiative and a number of other Republican leaders,” this person said. “It’s obviously a different opinion than [DeSantis] has.”
Other prominent DeSantis supporters are also in potentially difficult political positions. Tallahassee-based lobbying firms Ballard Partners and Capital City Consulting — both DeSantis allies that helped his presidential campaign — represent Trulieve, the Florida-based medical marijuana company bankrolling the amendment effort. The two firms acknowledged to NBC News that they have Trulieve as a lobbying client but are not involved with the amendment effort.
Anthony Farhat, a homebuilder and Florida-based Republican donor who knows DeSantis and Roe, said he has no doubt there’s tension between the two sides, but he thinks the perception of a rivalry is as much driven by staff who work for each as it is by Roe and DeSantis themselves.
“I don’t think either Ron or Jeff wakes up in the morning thinking about each other,” he said. “The down-line people, the staff, might, but I think to some degree its cast of characters stoke flames.”
“I have never heard Jeff say a cross word about Ron, quite the opposite,” he added.
Smart and Safe Florida, the political committee advocating for passage of the marijuana measure, has raised $100 million through September, nearly all of which has come from Trulieve. The committee has paid Roe’s firms more than $58 million since January 2023. The Florida Republican Party has officially come out against passing the measure, though GOP state Sen. Joe Gruters, a close Trump ally, has appeared in an ad supporting the effort.
“Amendment 3 has garnered broad support from Democrats, Republicans, Libertarians, and Independents across Florida because it champions the protection of individual freedoms and will end the unnecessary arrest of adults for simple marijuana possession,” Morgan Hill, a spokesperson for Smart and Safe Florida, said in a statement.
In combating the effort, DeSantis and his allies have homed in on the message that many public spaces could smell of marijuana if the initiative passes.
“The governor’s office hates Trulieve. I think it has to do directly with the amendment and Roe — not sure there was that level of bad blood previously,” a third person who worked on a pro-DeSantis effort said. “I would definitely say that as far as teams go, it is seen as [a personal rivalry].”
The person said DeSantis’ chief of staff, James Uthmeier, and his political allies would relish the opportunity to beat Roe after they believed he played a role in sinking their presidential campaign.
“And I am sure [Roe] feels the same way,” the person said.
Uthmeier declined to comment.
Farhat, the GOP donor who knows both DeSantis and Roe, however, said that the rivalry is not as intense as some think. He compared the situation to when legendary quarterback Tom Brady left his longtime team, the New England Patriots, a team owned by Robert Kraft.
“If you were to compare it to sports, I think the relationship is Robert Kraft and Tom Brady,” he said. “Both are Patriots through and through, but he went to the [Tampa Bay Buccaneers] and won a Super Bowl. [Brady] did not hesitate to go to New England and win a game there.”
“But when it was all over,” Farhat added, “they hugged it out.”
Matt Dixon reported from Tallahassee, Florida; Allan Smith reported from New York.
