Justin Leonard has long been remembered for one of the most iconic moments in Ryder Cup history. His 45-foot birdie putt! That alone turned the tide of Sunday singles at Brookline in 1999 and helped fuel the United States’ comeback over Europe. A performance like this would have demanded that Leonard captain Team USA one day. But years passed, and fans never saw his name on the roster. Now, finally, after much speculation, Leonard revealed what actually went down. It was he who closed this door for himself!

Speaking to Brandel and Bailey Chamblee on their The Favorite Chamblee podcast, Justin Leonard bluntly acknowledged the reality. “I do think my ship has probably sailed.” Why? Well, the 51-year-old believes that declining early opportunities to serve as vice-captain sent the wrong signal to those making future captaincy choices. It is a striking confession from someone who has a remarkable legacy in the Ryder Cup’s history. His Brookline heroics came when he was just 27, which brought several people’s attention to him. That year, he was approached about helping as a vice captain, but he declined.

Back then, he felt the timing was not right. Now, he sees how those rash decisions reshaped his Ryder Cup path. “I think it told too many people that make those decisions that the Ryder Cup wasn’t important enough to me, which couldn’t be further from the truth.” That year, the US went on to win 14.5 – 13.5 in what would come to be known as the “Battle of Brookline.” Leonard himself finished the week 1-1-1, with his Sunday birdie putt against Jose Maria Olazabal.

Overall, Justin Leonard played in three Ryder Cups (1997, 1999, 2008), posting a 2-4-6 overall record and collecting five career points. But after that, he didn’t hear from anyone again about a potential vice captain role, let alone captaincy for the Ryder Cup. It was not until very recently, in 2024, that he was offered to take up the role of an assistant captain for the Presidents Cup under Jim Furyk‘s leadership. And this opportunity made him realise further as to why he might never again get a chance to lead in the Ryder Cup. Interestingly, Furyk himself will be serving as this year’s Ryder Cup vice-captain for Keegan Bradley‘s Team.

To Leonard, the gap now is less about his past resume and more about his connection with today’s players. After working in television for NBC and the Golf Channel and now playing mainly on the Champions Tour, he has come to the understanding that he no longer shares the week-to-week grind with PGA Tour regulars. Drawing from his Presidents Cup experience, he recalls, “There were a number of players, I knew their bios, but I didn’t really know their personalities. I think it is important for a captain to understand their personalities. You don’t have to be friends with the guys, but you certainly need to know that. And part of knowing them is, is playing golf scenes…watching them practice a little bit, playing with them in tournaments…all those things. I think all that does make a difference when you’re trying to put a team together.”

This idea has only gained weight in recent years. Just look at Keegan Bradley, who became the youngest US Ryder Cup captain since Arnold Palmer in 1963. Bradley resisted the temptation to pick himself as a playing captain for Bethpage, despite finishing 11th in the standings, despite admitting that it “broke his heart” not to choose himself as a playing member on the team. His decision emanated from the task of being fully present as a leader rather than squeezing oneself on the roster just for the sake of it.

Had Bradley been on the playing squad, it would have been difficult for him to lead the team and be there as a captain. Having played with and against most of these players, he knows them, has a connection with them, and has the ability to manage their personalities, something he would use when pairing them up for the Ryder Cup. This exact thing Justin Leonard believes he lacks.

Even so, when pressed by Brandel Chamblee on whether he could reconnect with the new generation if given the captain’s job, Leonard didn’t hesitate. He showed eagerness to put effort into knowing them and hanging out with them just for that opportunity. “I would do it.”

It seems Justin Leonard has learned from his mistakes. But there are other talented players too, who have been giving away the responsibility of taking on the Ryder Cup’s captaincy.

Top players dodging Ryder Cup’s captaincy hat

If you are thinking players would learn from Justin Leonard’s mistakes, you are wrong. Two of the biggest names in golf, from both sides of the Atlantic, turned down the opportunity to lead a Ryder Cup team. In July 2024, Tiger Woods confirmed that he had turned down the opportunity as he was quite stretched at the time, juggling several roles on the Tour. He was busy with the job of a PGA Tour Policy Board member and was also a key negotiator in the merger talks between Saudi Arabia’s PIF/LIV. He straight away said that he couldn’t commit to the time the job demanded. It was then that the role passed down to Keegan Bradley.

On the other side of the shore, Rory McIlroy has also waved off early discussions about leadership. Last month, during the BMW Championship, he admitted that the idea of being a playing captain was floated, but he dismissed it as “impractical.” “The idea of me being a playing captain sometime soon has come up, and I’ve shot it down straightaway.” McIlroy pointed out how modern Ryder Cup captains are loaded with daily media duties, sponsor work, and several other team tasks that leave almost no room to focus on competing.

Do you think Tiger Woods and Rory McIlroy will be presented with the opportunity to lead their respective team after their blunt rejection? Or will they also regret their decisions like Leonard in the future? Let us know in the comments below.