Trump returns to Iowa, with a plan to avoid the missteps he made in 2016

DAVENPORT, Iowa – After he lost the 2016 Iowa Republican caucus, Donald Trump delivered a speech in which he pledged his love for the state and suggested he might even buy a farm there.

On Monday, the former president returned, not to visit a farm he didn’t end up purchasing but to try and win over the critical voters who, he hopes, will send him on his way back to the White House.

Trump spent the evening in the eastern part of Iowa, which traditionally hosts the GOP’s first-in-the-nation caucuses. After a stop at a restaurant where he snapped photos with customers, he talked up his prospects of winning the state that eluded him seven years ago.

He was in a notably good mood, with little indication that the legal troubles surrounding him were causing any stress. Indeed, he was feisty at times, going after his leading potential opponent, Florida Gov. Ron DeSantis, whom he derided as a “disciple” of former House Speaker Paul Ryan, “a RINO loser.”

“To be honest with you, I don’t think he’s going to be doing so well here,” Trump said of DeSantis.

He was also accessible, speaking with the press corps on multiple occasions and even giving the audience a chance to ask him questions. It felt, at times, reminiscent of that 2016 run, when he blanketed the airwaves and made himself a fixture among the mainstream outlets en route to a shocking primary and general election win.

Privately, Trump has made clear to his team he does not want a repeat of what happened in Iowa in 2016, during which he felt he was out-organized by his primary opponents and finished second to Texas Sen. Ted Cruz. He has recalled to people that his daughter, Ivanka, showed up to an Iowa caucus site only to notice that the campaign had little presence there.

The visit on Monday was an initial attempt to not repeat those missteps. It came just days after DeSantis made his own Iowa debut — a trip that also took him to Davenport, a city that borders the eastern part of the state and a regular stop for those seeking the White House. DeSantis, who is widely viewed as Trump’s most formidable potential primary opponent, has been promoting his newly released memoir in states that also happen to be early-primary ones. is embarking on a tour of early states as he promotes his newly released memoir. Former U.N. Ambassador Nikki Haley visited the state after launching her bid last month, and another prospective candidate, South Carolina Sen. Tim Scott, also recently made a stop in Iowa.

The trip began with the former president climbing aboard his personal plane — dubbed by aides as “Trump Force One,” and which is complete with gold-emblazoned seats and a sound system that blares oldies and “Phantom of the Opera.” — a little after 2 p.m. He was joined on the flight from West Palm Beach by a cadre of senior advisers, including Susie Wiles, Chris LaCivita and Brian Jack. He was also accompanied by Matt Whittaker, who served as his acting attorney general and is an Iowa native.

Not everyone in Iowa has been eager for a Trump revival. Some of the state's influential evangelical voting bloc has been cool to the thrice-married Trump’s 2024 bid. Bob Vander Plaats, a longtime evangelical figure in the state who endorsed Cruz over Trump in 2016, has even urged Trump not to enter the 2024 race.

But Trump has been making early moves in the state, where organization typically plays a major part in determining the outcome of caucuses. He has advocated for Iowa to remain first on the party’s nomination calendar — a cause near-and-dear to the state’s conservative activists — and for the last two years has placed full-page advertisements in Iowa Republican Party publications. He featured the Iowa GOP’s chairman, Jeff Kaufmann, at a rally he held in Sioux City last year, and he recently tapped Kauffman’s son, state Rep. Bobby Kaufmann, to be a senior adviser. Two other Iowa operatives, Alex Latcham and Eric Branstad, the son of longtime former Iowa Gov. Terry Branstad, have also been helping out.

Within many corners of the party, Trump’s campaign is regarded as more experienced and better prepared than the one he fielded in 2016.

The current race is competitive: A poll released by the Des Moines Register last week showed Trump and DeSantis with similar favorability numbers among the state’s Republicans — with 80 percent expressing a favorable view of the former president, compared with 75 percent for DeSantis.

Speaking to reporters at the Quad City International Airport upon his arrival, Trump expressed confidence in his prospects in the state and remarked that he won Iowa in the 2016 and 2020 general elections. He also expressed optimism that he would have the support of the state’s Republican governor, Kim Reynolds, given that he has endorsed her previously. (Those close to Reynolds, however, say she remains uncommitted in the race. In recent days, she has appeared with DeSantis, Haley and Scott.)

After leaving the airport, Trump headed to the Machine Shed restaurant in Davenport, where he posed for pictures with customers and asked them how the food was.

“They’re right about that,” Trump said as he posed for photos with a group of supporters wearing “Trump Won” T-shirts.

Trump’s motorcade then snaked to the Adler Theatre where, before a boisterous audience of more than 3,500 people, Trump touted his record, savaged President Joe Biden and tweaked DeSantis, saying that the governor had supported curbing agricultural subsidies and had pushed to scale back entitlement programs. The former president drew applause when he promised to protect Medicare and Social Security.

Trump’s team used the event to lay the groundwork for their organization in the state: Advisers said they had collected data — including names, home and email addresses and cell phone numbers — and would use the information to help ensure that the supporters would participate in next year’s caucuses.

David Kochel, a prominent Iowa-based GOP strategist and Trump critic, said that Trump is “in a position where he absolutely should win Iowa, given that he is the former president and starts with a ton of key contacts and a big base of support.” But, Kochel added, a win was no sure thing.

“There does appear to be a lot of folks who are keeping their options open, taking a look at who’s joining the field,” Kochel said.

But Nick Ryan, another Republican strategist in the state, called Trump “the favorite,” given his past incumbency.

“For anyone to beat him they would need to offer a compelling alternative,” Ryan said. “That takes a lot of time, even more work and a little luck.”