Caddie Confidential: Caddies share favorite Ryder Cup moments

Caddies share their favorite Ryder Cup moments. Credit: Bob Breidenbach/Providence Journal-USA TODAY NETWORK

Welcome to the ninth installment of our “Caddie Confidential” series, with monthly, inside-the-ropes perspective from dozens of Tour caddies on rotating golf topics. Up this month: we tackle all things related to this week’s Ryder Cup at Whistling Straits in Kohler, Wisconsin.

The Ryder Cup has produced countless unforgettable moments over the years.

But, in the eyes of caddies, which are the absolute best of the best? That was the topic of conversation for this installment of our September Caddie Confidential.

What’s the best Ryder Cup moment you’ve either been a part of, or particularly enjoyed watching as a lover of the game?

Check out this selection of responses from caddies:

2014 at Gleneagles, walking through the tunnel to the first tee was something I’ll never forget.


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Beating the No. 1 player in the world in singles.

The clinching putt and watching a group of players celebrating together.


I particularly enjoyed the time Hal Sutton made Woods and Mickelson play together in 2004 at Oakland Hills to prove a point when they didn’t like each other … and they took a beating. It was very embarrassing for Sutton. Very foolish move.

I’ve been there four times as a caddie with a record of 0-4. Even still, I enjoyed every minute!

Watching Justin Leonard make that putt at Brookline was something else.

1999 U.S. comeback at Brookline was special.

Can’t stand him, but Justin Leonard’s bomb.

Pepsi swinging the flag around and around on No. 17 at Medinah.

European team winning at Medinah for Captain José.

Interested in more from our September 2021 installment of Caddie Confidential? Be sure to check which team caddies think will win the Ryder Cup and why, as well as their explanations for Europe’s dominance since 1995.

You can view all the results from our entire Caddie Confidential by clicking here.

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