Trump eyes White House insiders to replace outgoing legislative affairs chief

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President Donald Trump is not expected to look far when selecting a replacement for outgoing White House Legislative Affairs Director James Braid.

Sources close to the president told the Washington Examiner that there are “a lot” of “qualified” staffers already working in the White House legislative shop who could be slotted in immediately to fill Braid’s shoes.

Three sources close to the White House specifically floated Braid’s deputy director, Jeff Freeland, as a replacement. Freeland currently serves as the administration’s top liaison to the House of Representatives. Another source similarly suggested that Braid’s other deputy, Katie Bailey, is in the running. She previously worked for Gov. Mike Braun (R-IN) while he was a U.S. senator.

One possible dark horse also floated for the job is Vince Haley, the director of Trump’s Domestic Policy Council. Unlike Freeland or Bailey, Haley has no prior experience working on Capitol Hill. He did, however, work directly under Deputy Chief of Staff for Policy Stephen Miller during Trump’s first term. Haley also worked for Newt Gingrich’s advocacy group and helped the former House speaker write multiple books.

A GOP lawmaker close to the White House told the Washington Examiner on Thursday that Trump will likely tap “someone either in White House [legislative] shop” or an “experienced senior staffer” from Capitol Hill.

“[Braid] has a bunch of deputies that I’m sure are pushing to be considered,” said the lawmaker, noting that the eventual pick would “have to have a good, candid relationship with members and James Blair,” the top Trump aide who took a temporary leave of absence to run the president’s outside political operation ahead of the midterm elections.

The White House declined to comment on personnel decisions.

A source close to the White House agreed Braid’s replacement is “most likely going to be an internal person” because being Trump’s director of legislative affairs is not “a sexy job for people to leave the private sector.” 

“What are you going to be dealing with? Impeachment and House oversight investigations?” the source asked. “Freeland already is the House lead. Pace McMullan left earlier this year. He would have been a name. And then Jay Fields as well, but he’s in the same situation as Pace. They already went to the private sector. Why are they going to really come back?”

The source added that Trump administration and congressional aides had “a tough time at the end of 2020 getting a job” after that year’s election that there is little incentive “to come back in the tail end of the administration” and “presumably sign up for a year and a half or two years.”

“Your job prospects are probably a lot better now than they are two years from now,” the person said.

Braid and Blair, “the Jameses” as they’re known in D.C., have worked hand in hand to whip critical votes on a number of Trump’s legislative priorities, including the One Big Beautiful Bill Act. The pair also spent weeks liaising with members of Congress to end the full government shutdown last year and the partial shuttering of the Department of Homeland Security this year.

Prior to joining the Trump White House, Braid spent roughly a decade staffing Republican members of Congress, culminating in positions as Vice President JD Vance’s legislative director and deputy chief of staff in the Senate. Vance’s vice presidential chief of staff, Jacob Reses, is also planning to exit his White House role by the end of the summer.

Still, outside advisers to Vance and people close to Braid waved off the idea that the departures signaled the ramping up of a potential 2028 presidential run on the part of the vice president.

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Two sources familiar told the Washington Examiner that, like outgoing press secretary Karoline Leavitt, Braid had “always” planned to leave the administration “around the midterms.” Braid, according to the White House, will leave his post in September and has already outlasted all four of Trump’s legislative directors from his first term.

“James is a WORK HORSE. He was back in the Senate like two days after his first kid was born, but it would not surprise me if he needs some family time,” one of Braid’s former Senate colleagues told the Washington Examiner. “I believe Jacob Reses was in the same boat with a child on the way.”

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