The Republican Who Outsmarted Trump

Photographs by Caroline Gutman Representative Thomas Massie, the renegade Kentucky Republican who fiercely guards his political independence, doesn’t love being on President Trump’s bad side. He would prefer not to have the president’s allies spend millions to defeat him in a primary. In fact, if Massie had his way, he’d be working for Trump right now.In his telling, in the weeks after the 2024 presidential election, the two men talked about Massie, a farmer who champions raw milk, becoming Trump’s agriculture secretary. Massie had formally endorsed Trump late in the campaign, offering to help him win over libertarians who might be tempted to stay home or vote third party in key battlegrounds. Trump had been appreciative, and the two had chatted by phone to hash out the timing of the endorsement announcement. “Just tweet it. I’ll retweet you,” Trump had told him.The rollout went smoothly, but Massie’s endorsement didn’t get him the job in Trump’s Cabinet. He was recounting this to me in, of all places, a bridal suite inside a converted barn in his northern-Kentucky district. Massie had just delivered remarks to a friendly crowd in the wedding hall downstairs, part of an acrimonious campaign that, if Trump gets his way, will be Massie’s last. The president’s allies are spending big to defeat Massie in a May 19 primary and prop up Ed Gallrein, a Navy SEAL and a political novice whom Trump personally recruited as a challenger. Massie first won election to the House during the pre-Trump Tea Party era and has handily prevailed in competitive primaries before. But he is also aware of Trump’s unique hold on the GOP: When the president decides he wants a Republican out of Congress, he usually gets his wish. Polls have given Massie a lead over Gallrein, who is not well known in the district, but his advantage is far smaller than in his previous reelection bids.Trump attacks Massie anywhere and everywhere, whether it’s on Truth Social (“A totally ineffective LOSER”), at an eve