Florida Gov. Ron DeSantis’s (R) salvo targeting former President Trump’s character this week has been met with questions from corners of the GOP over the effectiveness of his latest message as the world waits to see whether Trump will be indicted over a hush money payment to an adult film actress.

DeSantis has yet to announce his expected presidential bid and had been muted in his response to the flurry of barbs Trump has thrown his way. But this week he came out swinging against his onetime ally and Trump and his backers punched back.

Chief among their concerns about DeSantis’s latest attack lines: that character may not be a message that resonates with primary voters these days, and their view that DeSantis’s response to the possibility of Trump’s indictment has been ham-handed and botched.

“You look at college football, basketball [or] anything in this country — winning matters first,” Sen. Tommy Tuberville (R-Ala.), an early Trump supporter, told reporters. “Unfortunately, sometimes, character should be more involved. But people look for success, they look for people to get things done. … That’s the way it is.”

In the Monday press conference, DeSantis attacked Manhattan District Attorney Alvin Bragg (D) as a “Soros-funded prosecutor” who is trying to create a “political spectacle,” a common attack line across the GOP. 

DeSantis has largely not responded to Trump’s attacks on him prior to his criticism of the former president this week. (AP Photo/Phil Sears)

However, flares went up in Trump’s universe when DeSantis declared that he doesn’t “know what goes into paying hush money to a porn star to secure silence over some type of alleged affair.”

His sit-down with British journalist Piers Morgan, who has also been a target of Trump’s venom, emerged a day later, showing him questioning Trump’s chaotic management style and criticizing him for hiring people who did not align with his policy positions and leaked information to reporters. 

“I also think just in terms of my approach to leadership, I get personnel in the government who have the agenda of the people and share our agenda,” DeSantis said. “You bring your own agenda in, you’re gone. We’re just not going to have that. So, the way we run the government, I think, is no daily drama, focus on the big picture and put points on the board, and I think that’s something that’s very important.”

The comments from DeSantis, who is running second to Trump in the majority of primary polls, have broken with most other current or likely Republican presidential candidates. Former Vice President Mike Pence and former South Carolina Gov. Nikki Haley (R) are among those who have issued words of support for Trump in the face of the looming indictment. 

“It’s gutsy,” Sen. Kevin Cramer (R-N.D.), who has not endorsed in the 2024 race but has previously been critical of Trump, told reporters of the governor’s attacks against Trump. “He’s stepping into a big arena. It’s a big arena. He’s probably calculating that if he’s going to be in that arena, you can’t just take all the blows. You have to land a couple yourself.” 

According to a pair of GOP operatives, however, DeSantis was both too late to respond and too weak in how he did it to be effective.

“The attacks from this week are too cute by half and come off as childish,” one GOP operative told The Hill. “What’s happening this week, the party thinks it’s wildly unfair and the way President Trump is being treated is a total joke, and they’re rallying around him — and that’s from a lot of people who love him, people who hate him who think he’s being treated unfairly.”

“These attacks are being perceived as cheap shots. Kicking someone while they’re down,” the operative continued. “So I don’t think they’ve helped [DeSantis]. If anything, they’ve helped Trump.” 

A second GOP strategist also questioned whether DeSantis is the right messenger for the pair of attacks over the ex-president’s character. The operative argued Pence and Sen. Tim Scott (R-S.C.), who are viewed as top candidates for the evangelical, morality-based lane in an eventual 2024 field, would be more effective.

Both have supported Trump in the face of the possible indictment. 

Some GOP insiders have argued that DeSantis’s comments this week were too late and too weak to land any real impact. (AP Photo/Chris O’Meara)

“Donald Trump creates the playing field on which everyone’s playing on. He has the ability to create and shape what everyone’s talking about,” the second GOP operative said. “Your success in today’s Republican Party is dependent on your ability to play on his game board.”

“[DeSantis’s staff] could have had a camera on him in Tallahassee in 5 minutes on Saturday. He could have said it in an off-the-cuff line and it would have been fine instead of it coming days later and it feeling like it was a calculated line,” the operative continued. “When the two guys who can claim the moral high ground in their own response don’t criticize the moral failings, that means you’re probably wrong as well.” 

Adding to the issues for DeSantis, he has lost steam in recent months polling-wise after deciding to completely sidestep the various criticisms from Trump. Some Republicans believe that DeSantis may be in a period of transition from his reelection romp in November to a likely national campaign after the Florida legislative session wraps up in May. 

Trump’s latest missive toward DeSantis also arrived Wednesday, dismissing his work in office and laying the success of his in Tallahassee with his “great Public Relations” team. 

A week ago, GOP lawmakers were cringing at Trump’s attacks on DeSantis, concerned they were an early sign of a bitter and drawn-out primary.

But notably, a number of senators — spanning the spectrum of Trump backers to critics — on Wednesday either claimed they hadn’t seen the latest back-and-forth or just declined to comment. Sen. John Cornyn (R-Texas), who usually doesn’t hesitate to talk national politics, notably demurred when asked about the bitterness between the two GOP figures.

“Can we talk about like the AUMF [authorization for use of military force] repeal or —” Cornyn, who has not endorsed in 2024 but has criticized Trump, said with a laugh. He added it doesn’t do him much good to get involved.