Tiger Woods is a legend in the golf world, having registered a wide range of records to his name. However, there’s one name that often seems to surpass him, Jack Nicklaus. Notably, it’s usually these two that people argue on when they have a debate on who is the best golfer in the history of the game. The legendary caddie Billy Foster believes that Tiger Woods could have surpassed Jack Nicklaus if it were not for his health and one wrong decision he took.

Tiger Woods has won 15 majors in total, but Nicklaus is ahead of him with 18. Foster says that if Woods had remained in the top shape and continued to work with Butch Harmon, he could have easily gotten to 25 to 30 major wins. “I mean, if he stayed fit from 2008, if they stayed with Butch first and foremost, and if he stayed fit, you’re looking at a guy that had won 25 to 30 majors. It’s a travesty. He’s only won 15. He’s have won 120 playing left-handed, he were that good,” Billy Foster said during his conversation for On the Road with Iona.

The 15x major winner started working with Butch Harmon in 1996, primarily for his grip. They continued to work together till 2002, before Woods joined Hank Haney (2004-2010). While Woods enjoyed success working with both coaches, many believe that his time with Butch Harmon was way better compared to that with Haney. Golf Channel analyst Brandel Chamblee also blasted Woods for this crazy career mistake.

“It’s the craziest thing in the history of sport what Tiger Woods did,” Chamblee said.

With Butch Harmon, Woods won 8 majors and 34 titles with 33% and 26.8% win rates, respectively. On the other hand, he won 6 majors and 31 titles with 26% and 33.3% win rates, respectively, when working with Haney. Despite a good performance burst while working with Butch Harmon, Woods decided to part ways. This was because he felt that his coach was using his name for personal promotion.

Harmon’s comments for the media involving Tiger Woods were not liked by the 82x PGA Tour winner. According to the autobiography written by his caddie, Steve Williams, Woods didn’t confront Harmon directly about this. Instead, he chose the silent treatment and broke communication with him. When Harmon realized this, he confronted Woods and the two parted ways.

But it was not just this that stalled Tiger Woods from reaching the benchmark set by Jack Nicklaus and surpassing Sam Snead’s 82x PGA Tour titles. His health was also a major issue. “Unfortunately, you have countless back operations and dozens of knee and ankles and wrong legs and all sorts. It caught up with him, unfortunately,” Billy Foster said.

Tiger Woods has had seven back surgeries from 2004 to 2025. The most recent one happened in October 2025, when he had a lumbar disc replacement for L4/L5 collapse. Apart from these, he had many knee and leg procedures. This includes the 2002 ACL fluid/cysts removal procedure and the 2025 left Achilles rupture repair. Amid all these injuries, Woods did manage to get another major in 2019 by winning the Masters. However, the car accident he suffered in February 2019 never allowed him to make a proper comeback.

Billy Foster believes that the car accident did it for Tiger Woods, but he still is the best golfer the world has ever seen. And there would never be anyone else like him.

While Foster loves how Tiger Woods plays, he would have still hated to swap lives with him. Notably, he said this to the 15x major winner’s face when they worked together.

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Billy Foster caddied for Tiger Woods

Billy Foster joined Woods as a caddie for one week at the 2005 Presidents Cup. Woods’ regular caddie, Steve Williams, was not available because his wife was having a baby. Therefore, the 82x PGA Tour winner went to Darren Clarke to ask if Billy Foster could join him. With a little push from Lee Westwood, Foster agreed to do that.

This led to a controversy from the American team caddies. They were upset over a European looping for their star. This made Foster second-guess his decision, but Woods dismissed critics bluntly, saying, “‘F*** them, Billy.'”

Crowds adored Woods, but Foster emphasized the isolating downsides of stardom. Although Woods enjoyed billionaire status and GOAT acclaim, he had to face a lot of performance and stardom pressure. The legendary caddie stunned the golfer with a five-word reality check. He said, “I won’t swap our lives” during their brief partnership. The 2019 Masters champion responded in a positive manner, noting it was rare for someone to grasp his burdens.

Billy Foster’s reflections leave behind a lingering sense of what might have been, where talent, timing, health, and one pivotal choice intersected to reshape golf history. Even without rewriting the record books, Tiger Woods’ career, resilience, and impact still set a standard that continues to define greatness in the sport.