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 f

See Full Page