Tiger Woods could’ve won 25 majors if not for one big error, says PGA Tour caddie

Still, long-time PGA Tour caddie Kip Henley believes Woods had the edge over Nicklaus when it comes to swing.

Henley, who has worked with the likes of Vijay Singh and Stewart Cink, recently spoke about Tiger again after seeing more footage of his old swing.

The post read: “Flat wrist, down the line, on plane swing, no flip. Perfection.”

Henley responded on X: “People are entitled to their own opinions but mine is if he doesn’t change this action he wins 25 majors minimum. Maybe even more. He was just so much better than everyone else.”

The real reason behind Tiger’s missed opportunities is not just about his swing changes

Henley’s perspective is an interesting one, given his years inside the ropes with players like Singh and Cink. Still, there is a broader context worth considering.

After winning The Masters in 1997, Woods made notable changes to his swing – a move that led to 17 wins across the 1999 and 2000 seasons alone.

Plenty of players have overhauled their mechanics over the years, and Woods was only one more. He clearly believed it was what he needed.

The bigger hurdle, though, has always been his body. Woods recently had his seventh back surgery – a remarkable number that underscores how much he has dealt with physically.

And it is not just his back. Earlier this year, he also underwent Achilles surgery.

With those ongoing health issues and considering where his game is now at age 49, a move to the PGA Tour Champions might be on the horizon sooner rather than later.