Veteran caddie Michael Thomas ‘Fluff’ Cowan was the first to caddie for 15-time major champion Tiger Woods in a professional tournament, back in 1996. Although the two parted ways in 1999, Cowan still remembers what made Woods such an extraordinary player. Speaking on the Vanity Index Podcast last week, he recalled witnessing Woods hitting an unbelievable shot that “blew my mind.”

Although he admitted it was a “kind of a meaningless shot,” he remembered watching Woods hit a four-iron over a band of trees during what he believed was the Australian Open. The trees were so tall that Cowan felt most players, himself included, would struggle to hit even a sand wedge over them. The story prompted the host to ask whether working with Woods was ever challenging, given the extraordinary level of talent he possessed.

“I have to kind of disagree with you,” Cowan responded. “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.”

While Cowan doesn’t believe Woods is hard to work with, the perception may have stemmed from accounts shared by another former caddie. In his 2015 autobiography, Out of the Rough, Steve Williams, who caddied for Woods for 12 years between 1999 and 2011 and was on the bag for 13 of his major victories, claimed that the golfer sometimes treated him disrespectfully, even making him feel like a “sl**e.”

One particular habit that upset Williams was Woods casually throwing his clubs towards the bag and expecting him to walk over and pick them up. He also criticized Woods for spitting towards the hole whenever he missed a putt. Williams further discussed Woods’ behavior during the golfer’s 2009 scandal. He was particularly frustrated by Woods and his management team’s failure to communicate with him. 

At the time, Williams and his family were facing unwanted scrutiny despite having nothing to do with the controversy. The caddie also questioned the sincerity of Woods’ televised public apology, describing it as heavily scripted. Although Williams said he had no sympathy for Woods’ personal choices, he felt the golfer’s public humiliation was difficult to watch.

Woods dismissed Williams in 2011 following a dispute over Williams’ decision to caddie for Adam Scott. Sidelined by left knee and Achilles tendon injuries, Woods missed both the 2011 U.S. Open and the British Open. During that period, Scott asked Williams to caddie for him at the U.S. Open.

According to Williams, he first sought Woods’ permission and received tentative approval, but Woods later changed his mind. Having already committed to Scott, Williams says he chose to honor his word. Woods ended their partnership a few weeks after the U.S. Open, and the split became public on July 20. Woods has not publicly confirmed Williams’ account, and Williams has never said whether the episode colored his view of Woods.

Williams, however, has softened his view of Tiger Woods and his 2011 firing. That said, another of Woods’ caddies appears to have had a great experience working with the golf legend.

Less than three months after Woods split with Williams, he and Joe LaCava teamed up and developed a strong working relationship. However, 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. 

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

Woods then struck a beautiful shot that looked 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 he had a cheeky response when they reached the green and found the ball had actually finished just short of the pin: “Well, it’s not pin high.” Woods smiled, and LaCava knew they would get along.

At the end of the day, it’s difficult to say what working with Tiger Woods was like because most people don’t get to do that. But the majority appears to lean toward a positive experience.