DeSantis’ risky tactic: try not to trick donors

In the months before the 2020 presidential election, Roy W. Bailey, a Dallas businessperson, received a stream of text messages from Donald

Trump’s reelection campaign, asking for money in persistent, almost desperate terms.

“Have you forgotten me?” the messages read, Bailey recalled. “Have you deserted us?”

Bailey was familiar with the Trump campaign: He was the co-chair of its finance committee, helped raise millions for the effort, and personally contributed several thousand dollars.

“Think about that,” Bailey said recently about the frequency of the messages and the beseeching tone. “That is how out of control and crazy some of this fund-raising has gotten.”

He did, ultimately, desert Trump: He is now raising money for Governor Ron DeSantis of Florida, whose campaign has pledged to avoid the kinds of online fund-raising tactics that irritated Bailey and that have spread in both parties in recent years as candidates have tried to amass small donors.

No phony deadlines, DeSantis has promised donors. No wildly implausible pledges that sizable contributions will be matched by committees affiliated with the campaign. And no tricking donors into recurring donations.

This strategy is one of the subtle ways DeSantis’ team is trying to contrast him with Trump, who has often cajoled, guilt-tripped, and occasionally misled small donors.

For the DeSantis campaign, the vow of no trickery is risky. Trump, the most successful online Republican fund-raiser ever, has shown that such tactics work. But Generra Peck, DeSantis’ campaign manager, said that approach damaged the longterm financial health of the Republican Party because it risked alienating small donors.

So far, it’s difficult to tell if DeSantis’ approach is working. His fund-raising slowed after his campaign began in late May, and campaign officials did not provide figures that would have shed light on its success with small donors.

The battle to raise money from average Americans may seem quaint in the era of billionaires and super political action committees, which have taken outsize roles in US elections. But straight campaign cash is still, in many ways, the lifeblood of a campaign — and a powerful measure of the strength of a candidate. For example, GOP presidential contenders must reach a threshold of individual donors set by the Republican National Committee to qualify for the debate stage, a bar that is already causing some candidates to engage in gimmicky contortions.

“One of the biggest challenges for Republicans, across the board, is building out the smalldollar universe,” said Kristin Davison, the chief operating officer of Never Back Down, the main super PAC supporting DeSantis.

The DeSantis campaign said its strategy was devised to establish long-term relationships with small donors.