The single-coolest encounter I’ve ever had as the result of being a caddie was _________.

An extra special on-course encounter for Twitter user Garrett McInerney involved walking a hole with Charley Hoffman. Photo: @G87Mac on Twitter

You can meet a lot of people and have a lot of incredible experiences thanks to golf.

We recently asked out Twitter followers to fill in the blank:

The single-coolest encounter I’ve ever had as the result of being a caddie was _________.

As usual, our followers delivered with some tremendous answers, from rounds with U.S. presidents, to star athletes to Hollywood A-listers.

RELATED: Caddies share their biggest, on-course pet peeves

Here’s a collection of the best answers our followers sent in:

“One of my favorites was meeting the @jutanugarn sisters at the first tee, Kraft Nabisco 2011 during my walk-thru. Showed them the course. Later in the year, got the call and carried for Mo at the @LPG Panther Creek event where she made it through Sunday and Monday Q’s.” — @TourCaddieBlog

“Meeting Evander Holyfield.” — @SPARKSfly3131

“Meeting a United States President.” — @rhinoprojock

“Hole in one for @brady_schnell @KCGOLFCLASSIC. I pulled the perfect club. (He pulled the perfect club).” — @RyanCavanaugh24

“When I looped @ValhallaGolf @DavidNovakOGO gave me a generous tip and enough gift certificates for Taco Bell and KFC to get me through grad school. Much appreciated!” — @wjarviscoaching

“Met Bob Jones.” — @green_hitter

RELATED: The definitive guide to tipping a caddie | 23 hilarious caddie one-liners

“Having a beer in the Bay Hill locker room with AP after Kenny Perry won there in 2005… #TheKing #ArnoldPalmer #BayHillInvitational” — @ALanoII

“Caddied for Dave DeBusschere (old-time NBA player rated in top-50 all time) in a country club invitational.” — @Grace4Motown

“This February! Caddying for the sitting President and two guys with 33 majors between them.” — @johnlewman1yah1

“Caddied in a Pro-Am with Arnold Palmer in my group. What a day it was to watch Arnie play and to talk with him a number of times throughout the round!!” — @petrarca2110

“Tell Mario Lemieux he had to hit 7, not 8 & then him hitting it to 3 feet (made the putt) & him looking at me walking off the green saying, ‘we’re back tomorrow, will you be here?’ Great two days!” — @jpb1118

“Caddying for George Brett when I was 16.” — @Kygolfnews

“Caddied for Clint Eastwood at Cypress Point the day after ‘Unforgiven’ premiered. He was in a good mood!” — @bemil

“Neil Armstrong at Camargo in the 90’s. Such a nice guy.” — @DVaughan727

“Meeting @BarackObama on the 17th green/14th tee at Columbia Country Club on the Fourth of July!” — @Gus_Op

READ: How I became a PGA Tour caddie | Unwritten rules to caddying

“Caddied in the Palmer Cup (tri-st section/westpenn) at Latrobe. Was lucky to sit in the captain’s room and share a Rolling Rock Light and listen to Mr. Palmer tell some great stories.” — @imavillageidiot

“Cross-country from Florida one morning to LAX… straight to the Jet Strip.” — @OldSchoolCaddie

“The experience itself on the Korn Ferry Tour a few weeks ago. Hope to do it again.” — @jscottaz

“Jim Irsay. Slipped me a grand on the 18th tee at a non-tip facility.” — @govolx

“Working for Jim Kelly back before he was ever sick, at Boomer Esiason’s outing when it was just starting, had a 5 ball with Kelly as the celeb, just a down to earth great, great guy. Always rooting for him now.” — @tommysoxx

“Getting @MattDamonOnline as a guest one day at Black Rock CC. He was the nicest dude and walked/talked with the caddies (me and my brother) the entire round. Couldn’t have been cooler. This was right after Bourne Supremacy came out and we talked at length about the toaster move.” — @mgreeleyNGKF

“Looped for POTUS at the time B. OBAMA a few times on Martha Vineyard @ Vineyard Golf Club.” — @heals11

“Caddied in a celebrity tourney for @KellyHrudey once. Possibly the nicest guy on the planet.” — @coreystagg19

“Hitting a wedge on #9 at Augusta par 3 contest while caddying for a good buddy and past champion.” — @toddlyn32

“Caddying in Scottish Open pro-am at Gullane 2018 with Matt Kuchar and his caddie @Johnwould as our pro. Kuch was a nice guy & @Johnwould was top class.” — @gallser70

“Tiger asking if I wanted to jump on the shuttle to the range at Torrey, but me awkwardly declining because my player was in the crapper.” — @TedJrRice

“Maybe not cool, but funny… Mike Ditka’s wife arriving to the club in a Dodge Viper and telling me during the loop that the car is a great diversion for dealing with menopause.” — @vedderkj


  1. In the 1960s I was a student at UCLA and got a job as a caddy at the Bel Air Country Club. Many famous people were members. The first time I caddied for Dean Martin my only job was to drive the “ bar cart” and make and serve cocktails for the foursome. Another time I caddied for Jack LaLane who was a famous body builder and health and fitness guru. He always played alone and ran between shots, so, I had to run as well with a very big and heavy bag. There are many other great memories. The best part of the job was the really big tips we received.

  2. I caddied my way through college with the great Bob Collins (son of Patrick Collins)at Winged Foot golf club. Many of us started loopin’ for Gene Hayden in the early 70s.
    Truefully after more than decade of summers in the yard. learning the job with the Tuesday women’s club or sunday afternoon husband/ wife for <$10 to Bobby and i getting Trump and guests on a friday afternoon for $100 each. The 3 i will never forget… Arnold Palmer, Tom Watson, and the day i met, shook hands, shagged balls for and got an autograph from, Bob Hope

  3. I cadddied in the 80.s .a well known irish pro sacked me on the 18th in The Irish Open . He asked me to read a 40 foot putt .I replied 4 inches outside left lip then hesitated saying but maybe its straight as he was over the putt he missed it .missed the cut by 1 and sacked me there and then . Tony

  4. I caddied for Darius Rucker. He was and is still the coolest dude out there. We read and made a ton of putts together. Oh ! He was very generous!! Thank you Mr.Rucker you rock!

  5. I grew up caddying at Lakewood CC in Cleveland in the 70s. Had the club champs bag when he finished his round birdie – hole in one – birdie – birdie. Greatest finish ever! Oh, and he called the HIO too!

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