In this episode of Caddyshack to Corner Office, host Kai Sato chats with acclaimed sportswriter Rick Reilly, formerly of Sports Illustrated and ESPN as well as an 11-time winner of the NSMA's National Sportswriter of the Year Award. Rick shares captivating tales from his first caddying experience at The Masters for Tommy Aaron to humorous encounters on the bag with Donald Trump, John Daly, Tom Lehman, and Bob Newhart. From his early days in journalism to his celebrated book, Who's Your Caddy?, Rick reveals how caddying offers unique insights into golf and life. He also previews his upcoming sequel, Still Your Caddy, which covers a whole new spectrum of caddying, from looping in the nude to a transformational program using caddying to help soldiers with PTSD.

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[00:00:00] Rick Reilly’s humorous introduction to caddying at the Masters with Tommy Aaron.

[00:02:09] Rick's initial challenges and lessons learned as a caddy at Augusta National.

[00:03:48] Rick's passion for writing, early career, and working at Sports Illustrated.

[00:06:01] Upcoming book Still Your Caddy, spotlighting caddy school for soldiers with PTSD at St. Andrews.

[00:08:52] Rick’s experience at the world’s only nude golf course.

[00:10:11] Inspiration behind his popular book Who's Your Caddy?.

[00:12:48] Caddying for Donald Trump and humorous anecdotes leading to the book Commander in Cheat.

[00:16:28] Insights from looping for Tom Lehman and the importance of positivity in caddying.

[00:22:56] How Rick built trust and gathered behind-the-scenes caddy stories from the PGA Tour.

[00:25:33] Rick’s reflections on caddying as a partnership and a key takeaway from his experiences.

[00:28:12] The transformative role of caddying in the lives of soldiers with PTSD.

Links:

Kai Sato on LinkedIn: https://www.linkedin.com/in/kaisato

Rick Reilly on X: https://x.com/reillyrick?lang=en