When PGA of America Golf Professional Brennan Little teed it up in the 2024 Senior PGA Professional Championship late last September at Sunriver Resort in Oregon, no one in the field had a championship resume to rival the 54-year-old resident of Dallas, Texas.
Little arrived with a large, impressive portfolio with some 500 rounds on the PGA TOUR and 11 PGA TOUR victories, including the 2003 Masters and the 2019 U.S. Open — as a caddie.
He has been playing golf since age 10 and has been caddying on the PGA TOUR since 1999, and Little continues to build career highlights on both fronts. He finished T-26 in the Senior PGA Professional, his first appearance in the event, to earn a berth in the 2025 Senior PGA Championship (as a Corebridge Financial Team member) in May at Congressional Country Club in Bethesda, Maryland.
But as Little is quick to admit, it would take a succession of impressive victories as a player to match his career highlight reel as a caddie.
A native of St. Thomas, Quebec, Canada, Little teamed with fellow Canadian Mike Weir to win the 2003 Masters, marking the first major championship victory for a Canadian on the PGA TOUR. Little added a second major to his portfolio 16 years later when he carried the bag for U.S. Open Champion Gary Woodland at Pebble Beach.
“Winning the Masters with Mike (Weir) at Augusta National will probably always be No. 1 on my list of highlights,” says Little, who won eight tournaments with Weir. “I had a lot of great memories working with Mike, and we remain close friends to this day.
“Mike winning the Masters in 2003 was a huge victory for Canadian golf, and I was fortunate to be a part of it.”
After Weir experienced a series of injuries, Little caddied for Columbian Camilo Villegas for five years, which included winning the 2014 Wyndham Championship. Little then teamed up with Woodland two years later.
Woodland and Little won the Phoenix Open in 2018, and he helped guide Woodland to his first major victory the next year – the U.S. Open at Pebble Beach Golf Links. Woodland finished in style, birdying the final hole to finish with the lowest 72-hole score in six U.S. Opens at Pebble Beach and a three-shot victory over Brooks Koepka.
“Winning at Pebble Beach with Gary was right up there with winning with Mike at the Masters,” reflects Little, who turned 55 last month.
In late 2022 and early 2023, Woodland was experiencing tremors and shaking attacks, which he attributed to panic attacks. In September of 2023, he underwent surgery to remove a lesion discovered on his brain. When he returned to the PGA TOUR in 2024, the 40-year-old Woodland slowly regained his form and eventually made 15 cuts in 26 starts, including a Top-10 finish. The Woodland-Little tandem is expected to play 26 or 27 events in 2025.
“Anytime someone has brain surgery, there is cause for concern, but he has the entire golf community pulling for him,” explains Little, an ardent Dallas Stars fan who grew up following the Montreal Canadiens. “I think Gary will continually get better as time goes on.”
Little’s game got progressively better as a high school golfer in Canada, which prompted standout player Ben Kern to suggest he follow in his footsteps and play collegiate golf at New Mexico State University (NMSU) in Las Cruces, New Mexico.
“I enjoyed every minute of it,” reflects Little. “Coach Herb Wimberly (a PGA of America Hall of Famer) was a fantastic man and I have so many good memories of him.”
After graduating from the PGA Golf Management University Program at NMSU, Little completed his PGM degree in 1994. He then played the Asian Tour in 1995 and the Canadian Tour from 1995 through ’99. He worked for his college roommate — Martin Chuck, PGA — in Palm Springs, California, when not playing and was elected to PGA of America Membership in 1997.
By the summer of 1998, Little was looking for a new career path after it became apparent he wasn’t going to make much money playing professionally.
“Mike (Weir) and I grew up together playing junior golf and he had just finished his first year on tour. His caddie wasn’t coming back for a second year, and Mike asked me if I wanted to come caddie. It sounded like it would be a lot of fun and I started in January 1999 in Hawaii.
“I would never have imagined 25 years later that I would still be doing it.”
—Roger Graves
