For DeSantis, Overflowing War Chest Obscures the Challenges Ahead

As Gov. Ron DeSantis of Florida prepares to take a widely anticipated leap into the 2024 presidential campaign, one of his chief strengths is his ability to raise huge sums from deep-pocketed donors.

But his formidable war chest — at least $110 million in state and federal committees aligned with him — is no guarantee of success on the national stage, and his financial firepower brings with it a series of challenges he must navigate to capture the Republican nomination.

Mr. DeSantis’s unsteady debut on the national stage over the past month, including remarks about Ukraine that alarmed many Republicans and hesitant counterpunches against former President Donald J. Trump, has also showcased his aloof and at times strained relationship with donors.

Recent additions of seasoned advisers to his team and to an allied super PAC have allayed some concerns, strategists and donors said, but the early rookie mistakes, as one Republican donor put it, may have rattled influential would-be backers. Mr. DeSantis’s poll numbers have sagged against Mr. Trump, who has repeatedly taunted Mr. DeSantis and weaponized his fund-raising strength against him, painting the governor as a puppet of wealthy Republican elites.

Those barbs by Mr. Trump — who was largely forsaken by big donors even before his recent indictment by New York prosecutors — underscore the political reality that no matter how much money Mr. DeSantis has, he will have to overcome the grass-roots enthusiasm and army of small donors that Mr. Trump continues to command. The former president’s popular appeal was particularly apparent this past week, with his campaign announcing on Wednesday that it had raised $12 million off the news of his indictment.

Mr. DeSantis will also have to cultivate and tend to relationships with the everyday financial players in Republican politics — the millionaire donors, bundlers and fund-raisers whose enduring support is necessary to sustain a presidential campaign. He has, by many accounts, kept these donors at arm’s length while touring the country this past month, opting for rallies, book signings and closed-door meetings with allies instead of fund-raising dinners.

Though it is still early in the campaign cycle, some donors and strategists have questioned whether Mr. DeSantis’s skills as a politician are lagging behind his robust bank account.

“He is in the most enviable financial position of any candidate,” possibly including Mr. Trump, said Mike Murphy, a longtime Republican strategist. “There are questions in Republican circles about DeSantis’s candidate skills — can he make the transition from being the governor of a Republican state, where you exist on people’s TV screens, to the microscope of New Hampshire and Iowa?”

Mr. DeSantis also has a campaign-finance conundrum on his hands: Most of his money — more than $80 million, as of the end of February — is tied up in a Florida political action committee. He is prohibited by law from transferring that “soft” money — dollars raised without federally imposed limits — into a presidential campaign.

Who’s Running for President in 2024?

The race begins. Four years after a historically large number of candidates ran for president, the field for the 2024 campaign is starting out small and is likely to be headlined by the same two men who ran last time: President Biden and Donald Trump. Here’s who has entered the race so far, and who else might run:

Donald Trump. The former president is running to retake the office he lost in 2020. Though somewhat diminished in influence within the Republican Party — and facing several legal investigations — he retains a large and committed base of supporters, and he could be aided in the primary by multiple challengers splitting a limited anti-Trump vote.

Nikki Haley. The former governor of South Carolina and U.N. ambassador under Trump has presented herself as a member of “a new generation of leadership” and emphasized her life experience as a daughter of Indian immigrants. She was long seen as a rising G.O.P. star but her allure in the party has declined amid her on-again, off-again embrace of Trump.

Vivek Ramaswamy. The multimillionaire entrepreneur and author describes himself as “anti-woke” and is known in right-wing circles for opposing corporate efforts to advance political, social and environmental causes. He has never held elected office and does not have the name recognition of most other G.O.P. contenders.

Asa Hutchinson. The former governor of Arkansas is banking that in a crowded field, enough G.O.P. voters will be searching for an outspoken critic of Trump to lift his dark-horse candidacy. He has already made several trips to Iowa, testing his campaign message on voters who flocked to Trump in the past two elections.

President Biden. While Biden has not formally declared his candidacy for a second term, and there has been much hand-wringing among Democrats over whether he should seek re-election given his age, he is widely expected to run. If he does, Biden’s strategy is to frame the race as a contest between a seasoned leader and a conspiracy-minded opposition.

Marianne Williamson. The self-help author and former spiritual adviser to Oprah Winfrey is the first Democrat to formally enter the race. Kicking off her second presidential campaign, Williamson called Biden a “weak choice” and said the party shouldn’t fear a primary. Few in Democratic politics are taking her entry into the race seriously.

Robert Kennedy Jr. The son and namesake of Robert Kennedy, who was assassinated while running for president in 1968, filed paperwork on April 5 to run for president as a Democrat. Kennedy, a political activist known most recently for his campaign to discredit coronavirus vaccines, has not made a formal announcement yet.

Others who are likely to run. Gov. Ron DeSantis of Florida, former Vice President Mike Pence, former Secretary of State Mike Pompeo, Senator Tim Scott of South Carolina and Gov. Chris Sununu of New Hampshire are seen as weighing Republican bids for the White House.

Any move to use that money in support of his national ambitions, including transferring it to an affiliated super PAC, would still be likely to raise red flags among campaign finance watchdogs, although campaign finance experts said the Federal Election Commission, which has for years been deadlocked between the parties, was unlikely to act on it.

“Can he take that money, which was raised through his state PAC, and use it to advance his presidential campaign directly or through a federal super PAC supporting him?” said Saurav Ghosh, a former F.E.C. enforcement lawyer who is now the director of federal campaign finance reform at the Campaign Legal Center, a watchdog group. “The common-sense answer, and the law, says no.”

Mr. Ghosh added, “The unfortunate reality is that the F.E.C. is probably not going to do anything about it.”

In a statement, the F.E.C.’s chairwoman, Dara Lindenbaum, and vice chairman, Sean Cooksey, said any assertion that the commission’s bipartisan structure prevented it from fulfilling its mission was “misinformed.”

“Without commenting on any specific case, commissioners assess each enforcement matter on its merits, and we reach agreement in nearly 90 percent of them,” they said.

Representatives for Mr. DeSantis and for Never Back Down PAC, a super PAC that is expected to serve as a main vehicle for supporting Mr. DeSantis in a presidential bid, did not respond to detailed requests for comment.

At the end of February, as Mr. DeSantis began a national tour of speaking engagements and promotional events for his new book, his allies and backers stepped up preparations for a possible presidential run.

Friends of Ron DeSantis, a Florida PAC that had supported his successful re-election effort in November, continued to take in millions of dollars, including $10 million in February alone.

The vast majority of money the group has raised since the election has come from a few rich donors. Jeff Yass, a Philadelphia investment manager and major Republican donor, gave $2.5 million; Joe Ricketts, the founder of TD Ameritrade and an owner of the Chicago Cubs, gave $1 million; and Gregory P. Cook, a founder of a Utah-based multilevel marketing company that sells essential oils, gave $1.3 million.

Mr. Yass has given tens of millions of dollars in recent years to conservative and libertarian candidates and committees, including the Club for Growth PAC, an arm of a prominent conservative anti-tax group that has sought to move the Republican Party beyond Mr. Trump. Mr. Ricketts, the patriarch of a powerful political family in Nebraska, gave at least $1 million to support Mr. Trump in 2016, after initially opposing him in the primaries. Mr. Cook does not have a record of major gifts to federal candidates.

John Childs, a billionaire Republican donor in Florida, gave $1 million to Friends of Ron DeSantis in late February, as did Stefan Brodie, the founder of a Pennsylvania chemical company.

In March, Kenneth T. Cuccinelli II, a former Trump administration official, announced the creation of Never Back Down.

The group, now being run by the veteran Republican strategist Jeff Roe, said it had raised at least $30 million since March 9.

Super PACs, though powerful tools for pooling enormous sums of unregulated cash, come with drawbacks for candidates. For one, the campaigns cannot directly control how that money is spent. Crucially, television ads also cost more for PACs: Federal law lets candidate committees pay a lower price.

So the money raised by official campaigns — ideally from bundlers who can summon hundreds of friends and allies to max out their individual contributions, now capped at $3,300 per person — is often worth more to the candidate.

“You make me choose between a bundler and a big check writer, I’d rather have the hard dollars,” Mr. Murphy said. “Most bundlers really need to be pursued — and that goes back to the interpersonal skills.”

For that reason, Mr. DeSantis’s nine-figure haul is hard to compare to the $21.8 million that, at year’s end, sat in the federal campaign account of Senator Tim Scott of South Carolina, another potential Republican candidate.

Mr. Scott is also supported by a super PAC, the Opportunity Matters Fund, which since 2020 has raised tens of millions of dollars — including at least $35 million from the Oracle founder Larry Ellison.

And big-dollar fund-raising does not always translate to victory. Donors and strategists cite the examples of former Gov. Scott Walker of Wisconsin and former Gov. Jeb Bush of Florida as warnings. Cast as front-runners for the 2016 election, both took in huge cash hauls in 2015 — Mr. Bush raised more than $100 million — only to fizzle out of the race early.

In his recent stops in Iowa, New York, Pennsylvania and Georgia, Mr. DeSantis has offered a preview of how he might interact with donors as a national candidate. Some Republican donors, strategists and bundlers took note of what they said appeared to be Mr. DeSantis’s diffidence or even discomfort with the mingling and small talk that are staples of the campaign trail, particularly with contributors.

Many also said, though, that some donors and bundlers were waiting until the election cycle was further along to take a side.

Some were taken aback by Mr. DeSantis’s comments last month calling Russia’s invasion of Ukraine a “territorial dispute” and saying the war was not a vital U.S. interest. Those remarks, coupled with his aversion to old-fashioned “grip and grin” politics, may have given some supporters pause.

“I think he’s had a wobbly few weeks in communicating to donors,” said Rob Stutzman, a public affairs consultant who worked for former Gov. Arnold Schwarzenegger of California and for Mitt Romney’s 2008 presidential campaign. Donors keen to move on from Mr. Trump might “start to imagine — maybe this isn’t the way,” he said.

Mr. Trump’s campaign, which he announced in November, said at the end of January that it had raised $9.5 million — a sluggish start in comparison to front-runners from past elections. Though official numbers will not be out for several weeks, his campaign appears poised to see a significant boost after the indictment.

An affiliated super PAC, MAGA Inc., reported $54.1 million on hand at the end of 2022.

Last month, MAGA Inc. filed an ethics complaint with Florida officials accusing Mr. DeSantis of operating a shadow presidential campaign.

A spokeswoman for the governor’s office, Taryn Fenske, called the complaint part of a “list of frivolous and politically motivated attacks.”

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