Tiger Woods' Legendary Ex-Caddie Names Most Important Win of Career

Newsweek

08-07-2025

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After nearly 30 years as a professional golfer, more than 100 wins, and 15 major championship titles, it's difficult to pinpoint a specific turning point in Tiger Woods' career. However, there is no one better to do so than Steve Williams, the legendary caddie who worked with Woods during his most prolific years.
At the launch of his book, "Together We Roared", in his native New Zealand, Williams surprised everyone by pointing out the title that might have been most important in building the life-long legacy Woods went on to build.
And his assessment will very likely surprise you, until you understand the reasoning.
Tiger Woods' Turning Point
You were very likely thinking about one of his five Masters Tournament victories. But, you should know that Williams does not see it that way.
"Winning your second major is probably the most difficult thing there is in golf," the legendary caddie said.
"It's a lot of times you fall into the first one or you win it because you're not thinking of all the circumstances that go and how hard it is, but winning your second one is the hardest thing there is and for him it was no different."
15 Aug 1999: Tiger Woods poses with his trophy after winning the PGA Championships at the Medinah Country Club in Medinah, Illinois.
15 Aug 1999: Tiger Woods poses with his trophy after winning the PGA Championships at the Medinah Country Club in Medinah, Illinois.Exactly.
Winning the 1999 PGA Championship title is the turning point of Woods' career, according to Williams. He explained it from the perspective of the morale boost it represents for any player.
"If Tiger hadn't won the PGA [Championship] in '99, he would have entered the 2000 season still searching for that second major, and that would have been, you know, that might have been too much stress for him. He may not have had the career that he had," he said.
Woods won at Medinah with a score of 11-under, one stroke ahead of Sergio Garcia. Williams was a first-row witness, having begun working with Tiger earlier that season.
The veteran caddie illustrated his remarks with examples of how difficult it is to win a second major title:
"Look at Adam Scott on Sunday [at this past U.S. Open}, look at Justin Rose in the last two majors. These are two guys that are desperately trying to get to their second major championship, it's just nearly impossible. It's not impossible, but it's hard to do."
"Look at [2005 US Open winner, Kiwi] Michael Campbell, and the list goes on of how many players, and Tiger was no different."
After winning the 1999 PGA Championship, Woods enjoyed the most successful period of his career, which ended in 2009 and included 60 of his 82 PGA Tour victories. Twelve of those titles were major championships.
"Together We Roared" is a book written by Steve Williams and Evin Priest that chronicles the 15-time major winner's career during the 12 years Williams caddied for him. It was an impressive run that included no fewer than 13 major titles.
Woods and Williams parted ways in 2011. The legendary player has also worked with other illustrious caddies, such as Mike "Fluff" Cowan and Joe LaCava.
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