Tiger Woods transformed professional golf almost immediately after turning professional in 1996. Within months, he won his first PGA Tour title, then delivered a historic performance at the 1997 Masters, winning by 12 strokes at Augusta National.

Those early years helped establish Woods as one of golf’s defining figures.

His rise also brought together a team that saw his extraordinary talent up close, including veteran caddie Mike “Fluff” Cowan, who carried his bag at the start of his professional career.

Nearly three decades later, Woods remains a major subject of discussion as fans await clarity about his competitive future. Those who worked alongside him during his breakthrough years offer another perspective on the golfer’s remarkable journey.

Mike Cowan Reveals What Working With Tiger Woods Was Really Like

On the Vanity Index Podcast, Cowan pushed back against the suggestion that Woods was difficult to work with early in his professional career.

“I have to kind of disagree with you. He was actually quite easy [to work for], in my opinion anyway. He was easy, he was fun to work for,” Cowan said.

The veteran caddie explained that Woods’ extraordinary distance required one significant adjustment.

Cowan had to revise his yardage books because the young golfer produced carries he rarely saw with other players.

“But in all, it was a pretty easy job,” Cowan added.

Woods’ ball-striking also left a lasting impression.

“He had a sound off his irons, especially, I’d never heard. It was mind-blowing watching him hit in the beginning,” Cowan said.

Cowan worked with Woods from his professional debut at the Greater Milwaukee Open in September 1996 through early 1999.

Their partnership included the 1997 Masters, which remains the only major championship Woods won with Cowan carrying his bag.

Cowan also recalled a remarkable shot at the Australian Open, where Woods struck a four-iron over a tall band of trees.

“I watched Tiger one time in, I believe it was the Australian Open, he hit a four-iron up over this band of trees that most people, myself included, couldn’t hit a sand wedge over,” Cowan said.

He added that the shot stayed with him because Woods could launch the ball so high.

Steve Williams eventually replaced Cowan and later caddied for Woods during 13 major victories. The exact reasons Cowan and Woods ended their partnership aren’t entirely clear, but Cowan’s latest comments paint a positive picture of their time together.

Tiger Woods and Vanessa Trump Face Questions About Their Future

Away from golf, Woods’ relationship with Vanessa Trump has also attracted attention.

The couple has discussed marriage, though an engagement isn’t necessarily imminent.

“They’re very serious about each other and absolutely see a future together,” a source told Page Six.

The same source added, “Marriage is something they’ve talked about, but that doesn’t mean a proposal is necessarily around the corner.”

The relationship has continued through a challenging period for both.

Trump announced in October that she was cancer-free following treatment for breast cancer diagnosed earlier in the year.

Woods has also faced personal and legal difficulties following a March car crash in Florida.

Neither Woods nor Trump has publicly confirmed an engagement.

Meanwhile, Woods’ return to competitive golf remains uncertain.

Kevin Kisner has suggested Woods could target the Hero World Challenge and PNC Championship in December before potentially preparing for the 2027 Masters. However, those appearances remain possibilities, not confirmed commitments.

As fans await further updates, Cowan’s recollections offer a glimpse into the early career of a golfer whose influence extends well beyond the course.