Rep. Kevin McCarthy is a people person. He makes a point to remember details about his fellow House members, such as the names of their spouses and kids and their birthdays. “There is nobody better at understanding all the members and where they come from,” Jason Chaffetz, a former congressman from Utah who retired last year to become a Fox News contributor, tells me. The California Republican might be adept at the small gestures that can win people over, but as his failed bid to replace former speaker John Boehner in 2015 proved, those attributes are not necessarily enough to win him the speakership.

When House Speaker Paul Ryan announced this spring that he would be retiring after nearly 20 years in office, the Wisconsin Republican was quick to anoint McCarthy as his preferred successor. “I think we all believe that Kevin is the right person,” Ryan told NBC, arguing that McCarthy had gained much-needed experience as the majority leader since his first attempt to fill the job. But McCarthy finds himself today in a perplexing spot—if not a more challenging one—than he was in three years ago. Not only could the conservative House Freedom Caucus deny him the speakership amid policy disagreements as they did last time, but the approaching midterm elections in November could rob him of the opportunity altogether if Democrats retake the House.