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Trump, DeSantis look to sway Iowa GOP activists at dueling events

The Florida governor and the former president will share the spotlight on Saturday, providing a chance to sway influential conservative activists and contrast their campaign styles in Republicans’ leadoff voting state

Donald Trump
Former president Donald Trump at an event at the Adler Theatre on March 13, 2023, in Davenport, Iowa.Scott Olson (Getty Images)

Florida Gov. Ron DeSantis and former President Donald Trump will share the spotlight in Iowa on Saturday, providing a chance to sway influential conservative activists and contrast their campaign styles in Republicans’ leadoff voting state.

DeSantis, expected to announce his 2024 presidential campaign any day, is set to wade into Iowa’s hand-to-hand politicking at a congressman’s annual picnic and an Iowa Republican Party fundraiser, while Trump, a candidate since November, hopes to show strength with an outdoor rally with supporters.

Although the two men will be hours away from each other, the split-screen moment in Iowa is a first for the two national Republican powerhouses. It’s an early preview of a match-up between the former president, well ahead of his party rivals in early national polls, and DeSantis, who is viewed widely as his strongest potential challenger.

It will be DeSantis’ first trip to the early testing ground since the Florida legislature adjourned last week after spending months delivering the governor a conservative agenda that he’s expected to tout once he announces his campaign.

Trump, meanwhile, will be returning to the comfort of the campaign stage after a tumultuous week. On Tuesday, a civil jury in New York found him liable for sexually abusing and defaming advice columnist E. Jean Carroll and awarded her $5 million. A day later, during a contentious CNN town hall, he repeatedly insulted Carroll, reasserted lies about his 2020 election loss and minimized the violence at the U.S. Capitol on January 6, 2021.

DeSantis has burnished his reputation as a conservative governor willing to push hard for conservative policies and even take on a political fight with Disney. But so far, he hasn’t shown the same zest for taking on Trump, and even before he’s entered the race, he’s facing questions about his ability to court donors and woo voters.

His visit to Iowa will provide a test of his personal appeal as he mingles with local Iowa Republican officials, donors and volunteers, all under the glare of the national media.

DeSantis made his first visit to Iowa in March, promoting his memoir at events that drew more than 1,000 people in Davenport and Des Moines. Although DeSantis shook hands along the rope line near the stage after the events, he didn’t have a lot of interaction with voters. This time, he can expect a crush of introductions to influential caucus activists in a more conversational setting who will be taking his measure for the first time.

More than 700 people are expected to attend the Sioux Center fundraising event for Rep. Randy Feenstra at Dean Classic Car Museum, as well as dozens of news reporters from around the country. Later, DeSantis plans to headline a state party fundraiser in Cedar Rapids that’s expected to draw about 300 influential eastern Iowa Republicans.

Trump, by contrast, is headlining a rally expected to draw several thousand people to an outdoor amphitheater in Des Moines’ Water Works Park on Saturday evening.

Although Trump aides said the Des Moines event was in the works before DeSantis’ plans were made public, he and his team have long seen the governor as his only serious challenger. They hope a large rally of Trump supporters Saturday fuels comparisons to the scale of their respective events.

While Saturday is their first time in Iowa at the same time, Trump held a rally in Davenport three days after DeSantis did in March and took aim at him on renewable fuel and federal entitlements.

Saturday’s dueling appearances come as the emerging rivalry has turned increasingly personal.

DeSantis has largely ignored Trump’s jabs, which have included suggesting impropriety with young girls as a teacher decades ago, questioning his sexuality and dubbing him “Ron DeSanctimonious.”

DeSantis’ most pointed barb at Trump came in March, just before Trump was indicted on charges related to hush money paid to a porn actor. Asked by reporters about the prospect of an indictment, DeSantis said, “I don’t know what goes into paying hush money to a porn star to secure silence over some type of alleged affair. I just can’t speak to that.”

Trump’s campaign began airing an ad mocking DeSantis for yoking himself to the former president in 2018 when he ran for governor, even using some Trump catchphrases as a nod to his supporters in Florida.

Trump’s super PAC, MAGA Inc., also has been airing spots highlighting DeSantis’ votes to cut Social Security and Medicare and raise the retirement age. The group even targeted DeSantis’ snacking habits, running an ad that called for him to keep his “pudding fingers” off those benefits, a reference to a report in The Daily Beast that the governor ate chocolate pudding with his fingers instead of a spoon on a plane several years ago.

DeSantis has said he does not remember doing that.

A pro-DeSantis super PAC, Never Back Down, has hired Iowa staff and begun trying to organize support for the governor ahead of his announcement. The group has already begun knocking doors and announced Thursday that Iowa Senate President Amy Sinclair and Iowa House Majority Leader Matt Windschitl would endorse DeSantis’ candidacy. The group Friday rolled out another roughly three dozen GOP state lawmakers who would endorse him.

The super PAC also has been providing a more forceful response to Trump, suggesting that he should leave Florida if he’s unhappy with DeSantis’ governance, accusing Trump of not sufficiently supporting gun rights and siding with liberal Democrats.

“Trump should fight Democrats, not lie about Gov. DeSantis,” the narrator says in one ad. “What happened to Donald Trump?”

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