The great ones not only step off yardage, gauge wind direction and tend the flagstick, they also provide advice and encouragement. Sometimes a swing coach, often a life coach, and nearly always a shrink, a caddy is a PGA Tour player’s “other half.”
To win on Tour, a player needs a top-flight caddy on his bag. Here a dozen of the most legendary loopers of all time.
The concept of the caddy-as-quasi-celebrity began with Angelo Argea, who was born on this date in 1929. Sporting his trademark bushy gray Afro and gold neck chain, Angelo was with Jack Nicklaus for more than 20 years, helping the Golden Bear to 44 of his 70 Tour wins. Argea probably did less work than any caddy in history, never stepping off yardage, providing advice or reading putts. But he pulled clubs for the greatest player in history and landed in the Caddy Hall of Fame in 1999.
A veteran of more than 40 years on Tour, Mike “Fluff” Cowan has one of the most legendary mustaches in the game. Fluff won six times with Peter Jacobson before being hired by Tiger Woods. He was on the bag when Tiger lapped the field at the 1997 Masters, then was fired by the overly-controlling Woods after he revealed in an interview how much Woods was paying him. Cowan currently loops for Jim Furyk. The pair won the 2003 U.S. Open at Olympia Fields and Fluff later guided Furyk to a historic round of 58 at the 2016 Travelers Championship.
Bruce Edwards was Tom Watson’s stateside caddy. He was on the Hall of Famer’s bag from 1973 until they parted ways briefly in 1989 while Edwards went to work for Greg Norman. Diagnosed with ALS in 2003, Edwards continued to caddy for Watson until the strain became too much. The great Bruce Edwards succumbed to ALS at his home in Florida the day of the opening round of the 2004 Masters.
James “Tip” Anderson is one of the greatest caddies St. Andrews ever produced. Tip, who earned his nickname for offering advice, helped Arnold Palmer win both of his career Open Championships, in 1961 and ’62. When a hip injury kept Arnie out of the 1964 Open Championship, The King loaned Anderson as well as his putter to “Champagne” Tony Lima. At St. Andrews, Tip told Lima “just hit it where I tell you and you’ll do well.” Champagne Tony listened – and cruised to a five-shot victory.
Jeff “Squeaky” Medlin led Nick Price to three major championships. When Price skipped the 1991 PGA to witness the birth of his son, Medlin picked up alternate John Daly’s bag. In one of the greatest Cinderella stories in golf history, the man with the cartoon character voice-guided Daly around Crooked Stick for an improbable victory. Jeff Medlin, who died of leukemia at 43, was voted into the Caddy Hall of Fame in 1999, two years after his passing.
Andy Martinez has caddied for eight PGA Tour winners. He was with Johnny Miller for a dozen of the Desert Fox’s prime years. Martinez was on Tom Lehman’s bag for two decades and was there for Lehman’s triumph in the 1996 Open Championship at Royal Lytham & St. Anne’s.
Eddie Lowery is the focal point of the most well-known caddy photo in history. He was on the bag for Francis Ouimet when the 20-year-old amateur upended legends Harry Vardon and Ted Ray to win the 1913 U.S. Open at Brookline. Half the size and half the age of Ouimet at the time, Lowery became a wealthy San Francisco car dealer and later helped Ken Venturi and Tony Lema get their starts.
Steve Williams is the most recognized caddy of the modern era. The New Zealand native replaced Fluff Cowan on Tiger’s bag in 1999, and the pair reeled off 13 majors and more than 60 victories. Williams was part caddy and part security guard. At the height of Tigermania, he regularly had patrons removed from the course and tossed his fair share of cameras in the trash. Williams, who parted ways with Woods in 2011, won the 2013 Masters with Adam Scott.
Half of the most famous duo in golf history, Jim “Bones” Mackay was on Phil Mickelson’s bag from 1997 to 2017. One of the Tour’s power couples, he and Phil combined for 42 wins, including five majors. In 1990, Mackay was dubbed Bones by Fred Couples, who couldn’t remember the 6’4” string bean’s name. Mackay is now a television commentator, where he adds a unique insight to golf telecasts.
Alfie Fyles was Tom Watson’s man in Europe, where the six-time Player of the Year enjoyed his greatest success. During the 1970s and ‘80s, they cemented themselves as one of the most formidable tandems in Open Championship history, winning five together. At the famous Duel in the Sun at Turnberry in 1977, Watson wanted to hit six-iron into the final hole. Fyles coaxed him into a seven-iron, which Watson knifed to within two feet for the win over Nicklaus.
Herman Edwards was the long-time partner of Lee Trevino. The pair claimed six major championships over tumultuous years. Herman and the Merry Mex bickered so frequently that their on-course antics became the norm.
Joe LaCava made his reputation looping for Fred Couples during his prime. He has spent nearly three decades inside the ropes, caddying for Davis Love III, Justin Leonard, and Dustin Johnson. The 55-year-old LaCava has been on Tiger Woods’ bag since 2011. They won the 2019 Masters together, some 27 years after LaCava helped Couples to a Green Jacket in 1992.
