People involved in the campaign say Bossie has taken on a sensitive project: Running interference between DeSantis and Susie Wiles, the leader of Trump’s Florida operation. DeSantis had Wiles removed from her post after she clashed with him last year, before she was rehired against his wishes this summer. Bossie, who has a long-standing relationship with the governor, has been working to ensure the two are on the same page in a state Trump can’t afford to lose.
Bossie joined the president aboard Air Force One for two days last week when he made trips to Florida.
Trump’s preference for loyalists extends to the senior ranks of the White House, where 2016 alums Dan Scavino and Hope Hicks occupy powerful positions. Aside from Stepien, the campaign’s leadership includes 2016 aides Jason Miller and Justin Clark. Republican National Committee chair Ronna McDaniel forged a relationship with the president four years ago when she oversaw the Michigan state party.
Others are playing more behind-the-scenes roles. Oczkowski had initially been expected to spend most of his time working out of San Antonio, but has become a fixture in the campaign’s Arlington, Va., headquarters. Oczkowski, who in 2016 helped engineer Trump’s “Project Alamo” online campaign, is running a data modeling project to determine the president’s most promising path to victory.
State-level operatives who served on Trump’s 2016 effort are back and playing an even bigger role this time around. They’re shaping plans for the final weeks of the race, offering input on regular Saturday morning conference calls that Stepien has introduced. While they have been involved for months, senior campaign officials say their influence has recently intensified.
Some are determining Trump’s travel plans. During one recent call, Seitchik, who is helping to oversee Trump’s Arizona operation, pushed for the president to visit conservative Yavapai County. Following the advice, campaign advisers arranged for the president to hold a Monday rally in Prescott, the county’s population center.
Former Pennsylvania GOP chair Rob Gleason advocated for Trump to visit his hometown of Johnstown, a trip the president made last week.
They are also determining where Trump isn’t traveling. Trump told staffers on a Monday morning call that Bob Paduchik, a longtime loyalist who is steering his Ohio effort, had told him that he didn’t need to visit the state because he had it locked up.
Others, like Branstad, are driving decisions on where to send surrogates. The campaign has adjusted its plans in Florida based upon suggestions made by Wiles, who orchestrated Trump’s 2016 win in the state.
Senior campaign officials have compiled a roster of state-based staffers for the president to call, many of them 2016 alumni. He reached out to Branstad before traveling to Iowa last week, catching the aide by surprise while he was in his kitchen.
“When we talk, I’m very upfront, I’m very honest. I think that’s why he calls me because I’m straightforward and honest and want to do all I can to help him win,” said Branstad, who has resumed his role as leader of Trump’s Iowa operation.
Others are being invited along for rides on Air Force One. Gleason was on the plane during last week’s Pennsylvania trip and Wiles during last week’s stop in Florida. When Trump went to Ohio last month, Paduchik was aboard.
Some Republicans express concern that by relying so heavily on originals, Trump is getting overly positive feedback that doesn’t match up with reality. But to others, it’s to be expected for a president who has long gravitated toward familiarity and who loves to relive the glory days of his first campaign.
“It’s smart of the president,” said Andy Surabian, an adviser to Donald Trump Jr. and a 2016 alum, “to rely on the people who understand him and his movement.”