Confessions of a Caddie: Bag-Toters Dish the Dirt on Bad Golfers and Worse Tippers

It has been called both the best and worst job in golf – caddie. You lug the bags around the course all day and offer your golfer words of advice only to await the post-round handshake and hope that it’s filled with big bills.

The nature of the golfer-caddie relationship often creates some tense and humorous moments. Whether it’s a bag jockey at the local country club or a pro caddie carrying a bag on the PGA Tour, the true and tall tales are legendary.

Caddies have an inside look at pros behind the ropes and off the course, as well as observations of human behavior working for weekend warriors on the public links. Here’s a collection of their best jokes, quotes and anecdotes:

At the 2004 Buick Classic, caddie Randy Phelps got into a heated dispute with PGA Tour golfer Brenden Pappas on the 15th hole over a misread green. According to a story on ESPN, Phelps dropped the bag, took off his caddie bib, had some choice words for his soon-to-be former boss, and stormed off the course before realizing his fatal mistake. Phelps left his car keys in Pappas’ golf bag.

The encounter did have a happy ending, sort of. “I gave him (his) keys and a two-week severance paycheck,” Pappas said.

A hack got the chance to play at an elite country club with a fancy golf cart and complimentary caddie. He hacked and whacked his way around the posh layout all the way too the 18th green, where hefaced a gimme 2-footer for triple bogey. The caddie coughed during his putt as the shot lipped out and rolled 6 feet past the cup.

“You are the world’s worst caddie!” the hack shouted.

“I don’t think so,” the caddie replied. “That would be too much of a coincidence.

Last November, otherwise good guy Matt Kuchar came under fire for under-tipping his caddie after claiming the winners’ check of $1.2 million at the Mayakoba Classic. After initially giving fill-in caddie David Ortiz $5,000, Kuchar apologized and sent an addition check for $50,000 after being unmasked as a cheap skate and heckled by by fans on the course and on social media.

A hack was having a particularly bad round when he asked his caddie for advice on a short approach shot.

“Do you think I can get there with a 5-iron?” the golfer asked.

“Eventually,” the caddie quipped.

In perhaps the most infamous case of caddie interference on the PGA Tour in the 1980s came when the guy carrying the bag for Leonard Thompson committed a major faux pas. While pulling the pin on Thompson’s incoming putt, a golf tee fell from behind the caddie’s ear and into the path of the ball, forcing a miss and a two-stroke penalty. No wonder he chose to remain anonymous.

– A hack closed out a poor round and confided in his caddie, “I think this is the worst round I’ve ever played.”

“Oh the caddie said shyly. “I didn’t realize you had ever played before.”

– There are three unwritten but oft-repeated rules for caddies: Show up, keep up and shut up. Caddies only have one rule for their golfers: Pay up!

– A hack was dragging through a five-hour round and getting worse with every hole.

“Could you please stop checking your watch,” the hack said. “It’s distracting.”

“Yes sir, but this isn’t a watch,” the caddie replied. “It’s a compass.”

– Caddie Michael Collins might have summed up his career choice perfectly with this all-time quote:

“Caddies are even crazier than golfers. You know why? Because we know golfers are crazy, and we still want to work for them!”