10 Best Caddies of All Time

Caddies don’t get much credit on Tour, but in many ways, they should. After all, they are the ones right there with the best players in the world every step of the way working as a team to achieve a common goal. 

Here are 10 of the all-time great caddies on Tour.

Steve Williams

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Steve Williams is arguably the most recognized caddie in the modern era and maybe in the history of the game thanks in part to Tiger Woods. The legend from New Zealand was on Tiger’s bag in his prime beginning in 1999 where they ripped off 13 majors and a boatload of victories during their partnership. Not only was he his caddie, he also acted partly as security due to Tiger’s fame.

It wasn’t uncommon to find Williams picking people out of the gallery or tossing somebody’s camera in the trash. He and Tiger split in 2011, but Williams went on to work for another superstar named Adam Scott and won the 2013 Masters together, tying Tiger’s then major win mark of 14. 

Jim “Bones” Mackay

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Jim “Bones” Mackay was on Phil Mickelson’s bag from 1992-2017 and together established themselves as one of the PGA Tour’s power couples winning five majors and 42 wins (9th all-time). He also probably holds the record for pulling the most pins from over 60 yards. As the story goes, Bones got his nickname back in 1990 from Fred Couples who couldn’t remember his name. 

Mike “Fluff” Cowan

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Mike “Fluff” Cowan is a 40-year Tour veteran who has one of the most legendary mustaches in the game. He was on Tiger’s bag when he won his first major in historic fashion at the 1997 Masters. However, Woods fired him after he revealed his salary in an interview. He currently loops for Jim Furyk and was there for that historic round of 58 at the 2016 Travelers Championship.

James “Tip” Anderson


James “Tip” Anderson is one of the greatest caddies St. Andrews ever produced. Tip helped Arnold Palmer win both of his Open Championships in his career and was on his bag whenever he was across the pond. He got his nickname by offering you guessed it, tips while he was looping.

Angelo Argea

Angelo Argea was the caddie for Jack Nicklaus for over 20 years. During that time they won 40 times together. He was inducted into the Caddie Hall of Fame in 1999, but interestingly enough it’s been reported that Nicklaus did all the work on the course. All Argea really had to do was carry the bag and say the right things. Not a bad gig if you can get it.

Alfie Fyles

Alfie Fyles was Tom Watson’s man in Europe. During the 1970s and 1980s, they cemented themselves as one of the most formidable Open Championship duos winning a total of five together during that time. Miraculously, they had another shot to win in 2009, but the 59-year-old Watson lost in a playoff to Stewart Cink.

Terry McNamara

Terry McNamara was LPGA Tour legend Annika Sorenstam’s caddie during her illustrious career. Some would even call it the best in the modern era with 72 wins, the third most all time. 

Herman Mitchell

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Herman Mitchell was the longtime looper for Lee Trevino. Over the course of their 19-year relationship, they claimed 6 major championships, but that didn’t stop them from bickering and fighting along the way. Their on-course antics and disagreements became so normal, it was expected. Hey, whatever works. 

J.P. Fitzgerald

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J.P. Fitzgerald had a good run with Rory McIlroy. From 2008 to 2017, they teamed up to win four majors and ascend to World Number One. 

Bruce Edwards

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Bruce Edwards was the longtime caddie stateside for Tom Watson. He was on the Hall of Famer’s bag from 1973 through until they parted ways briefly in 1989 as he took a job to work for Greg Norman. But the two were reunited again in 1992 until 2003. Unfortunately, that was when Edwards was diagnosed with ALS. He lost his battle to the disease in 2004.