In the high-stakes pressure cooker of the Ryder Cup, every decision counts, and some choices can change everything. Back in 1999, as tension mounted and legends prepared to battle it out, one surprising move by Captain Ben Crenshaw left many scratching their heads.

Tom Lehman, a key player in the 1999 Ryder Cup USA Team, recently opened up about an era few truly understand when captain Ben Crenshaw made bold decisions that surprised many, including ignoring some of the biggest names on the team. Among those quietly passed over was none other than Tiger Woods, a player whose talent and toughness were undeniable but who was not the focus of Crenshaw’s game plan that day.

“Ben is one of those kind of mystical guys, so when he says things, you kind of pay attention. When he put me out first obviously, I felt some pressure. I know that if the first guy out loses, that makes the day a lot tougher,” Lehman told Ryder Cup USA. Ben Crenshaw had a unique way of leading  — calm, confident, and deeply connected to his players. His quiet presence carried a sense of purpose that instantly commanded respect. Crenshaw’s ability to connect on that deeper level made his decisions feel like more than just strategy; they felt like destiny.

Being the very first player to step onto the course in Ryder Cup play carries huge significance. The opening match sets the tone for the entire day: a win can ignite the team’s confidence, while a loss can make the path ahead much tougher. Lehman knew this well and felt the weight of that responsibility from the moment he was chosen to go out first. Naturally, he was nervous and far from fully confident. But then something changed.

“Ben had a way about saying things and doing things I would never forget as long as I live,” Lehman said, recalling the captain’s unique leadership style. Crenshaw wasn’t just focused on strategy; he understood the mental game better than most. Lehman vividly remembers, “I was in the locker room stretching, and he walked up, and he put his hand on my heart, just put it right there, and he said, ‘Do you know why I put you up first today?… I put you up first because you are the toughest guy I know.’ Whether he meant it or not, it didn’t matter.” He added, What mattered most to Lehman was the impact of that moment, the surge of courage and confidence it gave him as he prepared to face one of the biggest challenges of his career.

And in many ways, Ben Crenshaw was right to put his faith in Lehman. At the time, Lehman was one of golf’s most dominant players. He was coming off the prime of his career, winning the prestigious Open Championship in 1996, along with the Tour Championship the same year. The late ’90s marked the best period of his professional journey, and his consistent performance made him a natural choice to set the tone for the team. The 1999 Ryder Cup was the most memorable and one of the most controversial Ryder Cups as well.

In the 1999 Ryder Cup itself, Lehman justified that confidence by playing a pivotal role in the American team’s dramatic comeback victory. He scored 2 out of a possible 3 points, winning his singles match in a crucial win over Lee Westwood. Crenshaw’s decision to send Lehman out first was not only a bold leadership move but a strategic masterstroke that paid off in a high-pressure environment. Lehman was tough, but he wasn’t the only one. Captain Crenshaw made the surprising decision to sideline several top stars who were dominating the game at the time, none more so than Tiger Woods.

“I mean, there were a lot of rough guys on that team. Pretty hard to say Hal Sutton wasn’t a tough guy and that Tiger’s not a tough guy,” Lehman said. There were lots of dominating players in the field, like Woods and Hal Sutton, but the captain completely ignored these forces. Woods was also in his prime at that time, but not for the captain.

In 1999, Tiger Woods played 21 events and didn’t miss a single cut. He finished in the top 10 sixteen times and won eight tournaments, including the PGA Championship. He also came close to winning the U.S. Open, finishing tied for third. With a record like that, who could say he wasn’t the toughest guy on the field? In fact, many would argue he was the toughest of them all.

But maybe that comment was just to boost Lehman’s confidence; that’s exactly what he needed that morning. “He knew exactly what I needed to hear that morning… that made a big impact on me.” And that impact was real; history shows Lehman delivered when it mattered most. Ben knew what he was doing right from the start. 

The leadership that carved the U.S. name in Ryder Cup history

Ben Crenshaw’s captaincy during the 1999 Ryder Cup was a masterclass in leadership and belief. Even when the U.S. team faced a daunting deficit down 6-2 after the first day and trailing 10-6 after two days, Crenshaw never lost faith. He constantly adjusted the lineup, trusting his instincts and the players’ abilities. “I know how well these guys can play, and I know how determined they were,” he said, showing unwavering confidence in his team’s potential to mount one of the greatest comebacks in golf history.

What set Crenshaw apart was not just his strategic decisions but his ability to inspire and motivate. He sent his strongest six players out first: Tom Lehman, Hal Sutton, Phil Mickelson, Davis Love III, Tiger Woods, and David Duval to build momentum early in the singles matches. “I’ve never seen such firepower going out in the first six groups. It ignited everybody,” Crenshaw said. His bold move energized the team, sparking a winning streak that shifted the entire competition’s momentum.

Beyond tactics, Crenshaw’s emotional leadership played a crucial role. When the team neared victory, he urged them and the crowd to “Don’t stop believing,” a rallying cry that captured the spirit of the moment. He also brought in motivational support, including a stirring speech from George W. Bush, reinforcing the team’s determination to fight until the very end. Crenshaw’s captaincy wasn’t just about golf strategy; it was about instilling belief, resilience, and passion, helping the U.S. team etch its name permanently in Ryder Cup history.