There was a psychological tax that came with following Tiger Woods around a golf course. At least, that’s the impression fans were left with after reading his former caddie Steve Williams’ autobiography. Woods would allegedly toss his clubs towards the golf bag and expect Williams to walk over and pick them up. It was an uncomfortable experience, and it didn’t matter whether the legendary golfer had won or lost. The revelations painted a rather unflattering picture of Woods in front of the golfing world.

But if you turn to the man who stood alongside Woods at the very beginning of his empire, that perception starts to shift. Speaking on the Vanity Index Podcast, Mike “Fluff” Cowan challenged the popular narrative surrounding the 15-time major champion. The host of the show asked him whether Woods was ever challenging to work with, given the extraordinary level of talent he possessed. Cowan responded:

“I have to kind of disagree with you. He was actually quite easy. The one thing that I had to do was readjust my yardage books because I needed carries that I had never needed before. But in all, it was a pretty easy job.”

Cowan knew Woods from the very beginning of his professional career. He was on the bag when the young golfer made his professional debut at the 1996 Greater Milwaukee Open and stayed with him until 1999. That also meant Cowan was alongside Woods when he announced himself to the golfing world with his historic 1997 Masters victory.

Joe LaCava, who was Woods’ caddie between 2011 and 2023, also had a fairly pleasant time with him. A funny exchange during their first tournament together convinced LaCava they would get along just fine. The incident took place at the 2011 Frys.com Open.

LaCava recalled that Woods had barely asked him anything throughout the day before approaching him on a par-3 hole and asking whether he could reach the pin with a 7-iron. The caddie replied:

“You can get it on top, but you can’t get it to the hole.”

Woods then struck a beautiful shot that appeared to finish about 10 feet right of the hole, pin high. LaCava said he got a look from Woods that seemed to say, “Don’t ever tell me I can’t do something.” But when they reached the green and found the ball had actually finished just short of the pin, he had a cheeky response: “Well, it’s not pin high.” Woods smiled.

Williams, however, had a very different experience. Their relationship wasn’t always strained. Woods was even the best man at the caddie’s wedding in 2006. But their time together on the golf course eventually took a toll on that friendship.

Williams caddied for Woods for 12 years between 1999 and 2011 and was on the bag for 13 of his major victories. Yet, in his autobiography, he claimed that Woods sometimes treated him disrespectfully, even making him feel like a “sl**e”.

Williams also criticised Woods for spitting towards the hole after missing putts. Things became more difficult during Woods’ 2009 scandal, when reports of his extramarital affairs became public. Williams was particularly frustrated by the lack of communication from Woods and his management team, especially as he and his family faced unwanted attention despite having nothing to do with the controversy. He also questioned the sincerity of Woods’ televised apology, describing it as heavily scripted.

Their partnership eventually ended in 2011 after a disagreement over Williams caddying for Adam Scott at the U.S. Open. Woods was sidelined with knee and Achilles injuries at the time, and Williams says he initially received permission to work for Scott before Woods changed his mind. Having already committed to the Australian, Williams chose to honour his word. Woods ended their partnership a few weeks later, with the split becoming public on July 20.

The two went nearly a decade without speaking but have since put their differences behind them. Their experiences show just how differently Woods could be perceived by those closest to him. And while it’s difficult to say exactly what working with the golf legend was like, Cowan and LaCava’s accounts suggest it wasn’t always the difficult experience Williams described.

Cowan had another rather interesting reason for remembering Woods so fondly. During the podcast, he recalled one particular shot that had stayed with him for years. He believed it happened at the Australian Open, where Woods hit a four-iron over a band of trees that were so tall Cowan felt even a sand wedge wouldn’t have been enough for most players.

It wasn’t necessarily a shot that decided a tournament, but it left a lasting impression on the veteran caddie. Woods had an unusual ability to launch the ball high into the air, and Cowan admitted that watching him do it was “mind-blowing”.