“No matter what decision I make, I’m going to be defined by this decision,” said Keegan Bradley when asked whether he will be in the Ryder Cup as a playing captain. The conversation around whether he wants to play has only intensified since his appointment in July 2024, when the notion immediately arose about his chances of not only leading but also competing. And now, none other than Donald Trump has joined the conversation, adding even more weight and intrigue to Bradley’s looming decision.

Donald Trump posted, “Keegan Bradley should DEFINITELY be on the American Ryder Cup Team – As Captain!!! He is an AMAZING guy. It will be a great Ryder Cup. At the invite of the PGA Tour, I will be there on Tournament Friday!!!” Ranked 13th in the world, Bradley has proven form with 8 PGA Tour wins, 11 runner-up finishes, and 39 top-5s across 373 events, amassing over $55 million in career earnings. Fresh off wins in 2024 and 2025, he brings both performance and charisma to the role. He could even make history as the first playing captain since 1963, thanks to a rule change out of the way that allows vice-captains to step in while he competes, which was even backed by Luke.

On the surface, Team USA looks solid with its veteran leaders, but the real intrigue lies in the forces shaping the week. With seasoned leaders like Webb Simpson, Jim Furyk, Brandt Snedeker, Kevin Kisner, and Gary Woodland beside him, Team USA appears well-prepared for Bethpage Black. Yet Trump’s presence ensures the storyline stretches beyond golf alone. His remarks on ticket prices and his commitment to attend highlight how the Ryder Cup has become more than just a competition—it’s a cultural moment.

This dynamic takes on even more weight when compared to history, particularly the shifting expectations of Ryder Cup captains. Bradley’s situation is being compared with that earlier transitional period when legends like Nicklaus and Palmer shaped the captain’s role. After Arnold Palmer served as the last playing captain in 1963, the PGA of America barred captains from competing, believing the responsibilities were too great. That changed in December 1982, when Jack Nicklaus was named U.S. captain, and the committee unanimously voted to allow a captain to play. Nicklaus nearly qualified outright for the 1983 matches by finishing one shot behind Hal Sutton at the PGA Championship, but he ultimately chose not to select himself. This left the door open for future captains, and today it serves as the foundation for Bradley’s opportunity to revive the role of a playing captain more than six decades later.

Meanwhile, Trump’s personal stake in the game ensures that the story expands well beyond Bradley and the U.S. team. Trump’s deep ties to the game only amplify this. He owns 18 courses worldwide, including Trump National Doral in Miami and Trump Turnberry in Scotland, both of which have hosted major PGA Tour and LIV Golf events. Beyond ownership, he remains an active golfer himself, regularly appearing in Pro-Ams and casual matches, ensuring his name stays closely linked with the sport.

His influence is not new, as Trump has repeatedly inserted himself into the golf conversation—sometimes as a supporter, other times as a central character, there have been many instances, whether it was praising legends like Arnold Palmer, building friendships with golfers such as Bryson DeChambeau, or personally congratulating winners like Grant Forrest. Bryson once said, “His driver swing is the most repeatable thing I have ever seen. I wish mine were that repeatable. Really, I do.” He also added, “He’s actually a really good golfer. He stripes it down the middle of the fairway and has good iron game and putts it pretty well.” These comments, along with Trump’s habit of FaceTiming champions and hosting high-profile events, illustrate how his presence consistently blends politics, sport, and personality—keeping him firmly in the spotlight of golf’s biggest storylines.

One of the more memorable examples involved Keegan Bradley’s current caddie, when an offhand comment about one of Trump’s courses created a stir both on and off the fairways.

When Keegan Bradley’s Caddie Had to Apologize to Trump

Keegan Bradley’s current caddie, Scott Vail, once found himself in hot water with Donald Trump after making a blunt remark about one of Trump’s courses. Back in the mid-2010s, while working for Brandt Snedeker at the WGC-Cadillac Championship at Trump National Doral, Vail vented his frustration on social media, calling it the “worst golf course I’ve ever caddied on.” The comment quickly made headlines, sparking backlash from Trump’s camp and leaving Vail worried about his job. Snedeker’s family and management urged damage control, and it soon became clear that an apology would be required.

Vail later revealed that Trump’s associates demanded he personally write an apology email. Snedeker himself had already sent a formal note, which drew a curt but memorable reply from Trump: “Thanks very much for the email apology, Brandt, the boys love the golf course, it’s a great golf course… oh by the way, your caddie’s a moron and you should fire him.” Vail eventually sent his own short apology, though Trump never responded. Looking back, he admitted it wasn’t his smartest decision, but the incident underlines how Trump’s influence and sensitivity around his golf properties have long shaped the sport’s off-course drama.