Look, being a Ryder Cup captain isn’t for the faint of heart. You’re juggling egos, managing personalities, and making decisions that can define careers. But ask any former captain what keeps them awake at night years later, and they’ll tell you it’s not the pairings or the strategy calls. It’s something much more personal—a choice so uncomfortable that some have sworn to take it to their graves.

Right now, both Keegan Bradley and Luke Donald are facing that exact nightmare. As the 2025 Ryder Cup captains prepare for Bethpage Black, they must confront golf’s most emotionally devastating regulation: the envelope rule. The envelope rule forces both captains to secretly choose which player on their team they trust the least.

The rule has sparked so much discussion that Claire Rogers from Golf.com recently joked about applying it in workplace settings, tweeting: “In honor of the Ryder Cup’s envelope rule, I will be putting one coworker’s name in an envelope to start the week at Bethpage.” Her humor highlights just how uncomfortable this decision feels—even in non-golf contexts. But for Bradley and Donald, this isn’t a joke—it’s their shared reality.

Both captains must write down one name before Sunday’s singles matches begin. If someone from the opposing team gets injured and can’t play, the envelope gets opened. That chosen player sits out automatically. Both matches then count as half-points. However, the true devastation lies in what this decision does to the captains themselves.

The psychological toll on captains proves overwhelming in ways most fans never realize. Curtis Strange called it “the most uncomfortable thing I ever had to do” as a Ryder Cup captain. He explained the full emotional weight during the 2002 tournament: “The whole thing is very uncomfortable, writing the name on the paper, sealing it in the envelope. You don’t ever want that name to get out. You don’t ever want to destroy someone’s confidence. But you’re obligated to put a name in the envelope. These guys become family, and it’s like you’re telling one of them you don’t love them as much.“ Yet the isolation both Bradley and Donald face goes even deeper than Strange’s experience.

Both captains must bear this burden completely alone, unable to share the weight with anyone. Steve Stricker revealed his isolating approach in 2021: “I probably will talk to my assistants and then probably not tell them who I put in there. You don’t want to have anybody know that they went in the envelope. At least I wouldn’t want to know if I was in there, and I probably was in there at some point.” This secrecy creates an even more disturbing reality for captains.

Padraig Harrington described the decision as choosing which player to sacrifice. “The person that goes in the envelope, the captain decides, and nobody ever knows,” he stated before explaining that captains hope the secret stays buried forever. This secrecy requirement means both Bradley and Donald must essentially rank their players in order of dispensability. That reality creates profound discomfort for leaders who view their teams as family—and history shows just how badly this can go wrong.

Ryder Cup controversies that should worry Bradley

The envelope rule has only been invoked three times since 1979, but each instance created significant drama that should terrify Bradley as he prepares his team. The worst-case scenario already happened to an American captain, and it still haunts the sport today.

The most controversial use occurred during the infamous 1991 “War on the Shore” at Kiawah Island. Steve Pate suffered injuries in a car accident during tournament week. When U.S. captain Dave Stockton pulled Pate from Sunday’s singles, it triggered the envelope rule unexpectedly. What happened next shows exactly what Bradley hopes to avoid.

European captain Bernard Gallacher had placed David Gilford’s name in the envelope. The situation devastated Gallacher so much that he asked assistant Tony Jacklin to break the news. Gilford, a rookie making his Ryder Cup debut, was “on the verge of tears” and “very upset” at the announcement. But the controversy didn’t end there—it got much worse.

Gallacher had never told Gilford about being in the envelope, creating a shocking surprise for the young player. The captain later admitted he would have preferred discussing the possibility with his entire team beforehand. More damaging still, Gallacher felt completely manipulated by the situation.

Gallacher bluntly stated: “I think the Americans turned us over there,” believing they exploited the system to avoid a potentially difficult matchup between Pate and Seve Ballesteros. This controversy serves as a warning for Bradley about how envelope decisions can create lasting resentment and accusations of gamesmanship. Fortunately, history also shows there’s a better way to handle this nightmare.

The 1993 instance demonstrated the rule’s potential for sportsmanship rather than controversy. When Europe’s Sam Torrance couldn’t play due to a sore left foot, American veteran Lanny Wadkins volunteered himself for the envelope. This selfless act made Captain Tom Watson’s job significantly easier. Bradley might hope for similar team unity from his players, but he can’t count on it.

This lasting secrecy requirement explains why Bradley likely dreads the envelope rule more than any other captain’s duty. He must make what amounts to a secret declaration of relative player value at the tournament’s most pressure-filled moment. That decision will haunt him long after his captaincy ends—regardless of whether Team USA wins or loses at Bethpage Black.