PGA Tour pro, Gary Woodland has been on tour since 2007 and has employed a number of caddies during his six-win career so far.
But, his most recent on-course partnership is also his longest and most successful, turning to the highly-successful Brennan Little towards the end of 2016 and remaining with him ever since.
Little - born in Ontario, Canada but now living in Plano, Texas - has been a pro caddie since 1999 and worked with the likes of Mike Weir, Sean O'Hair and Camillo Villegas along the way.
His career highlights include helping Weir to victory at the 2003 Masters and then guiding Woodland to the 2019 US Open title at Pebble Beach, plus several other wins on tour and six Presidents Cup appearances.
While obviously an excellent caddie, Little is also quite the player, too. He revealed during a 2019 interview with the Caddie Network that he held a Handicap Index of two at the time and used to play collegiate golf at New Mexico State.
According to his profile on the PGA of America, Little has won seven Northern Texas Section titles throughout his career - including three in five starts during 2024. The pro bagman was also set to make his Senior Major debut in 2025 after qualifying for the Senior PGA Championship - at which Woodland was slated to reverse roles and caddie.
Explaining how the move came about, Little said: "[Gary] told me that when I turn 50, if I qualify for a Major, he'd caddie for me. I qualified through my section and went to the National Club Pro out in Oregon. I got him panicked there for a while and almost blew it, but I ended up making it so I'm holding him to it."
A role reversal for @GaryWoodland!Brennan Little (Woodland’s caddie) is competing in this year’s Senior PGA Championship.Woodland will be on the bag for his right-hand man. pic.twitter.com/Te2CYvlRqkFebruary 27, 2025
The Canadian's favorite golfer growing up was Greg Norman and his favorite golf course to caddie at is Augusta National. That being said, Little admitted he has a lot of time for Colonial due to knowing the golf course really well and it being close to his home in northern Texas.
As far as personal interests go, Little loves playing and watching ice hockey with his dream alternate career being the general manager of a hockey team. He supports Dallas Stars (NHL), Washington Commanders (NFL) and Toronto Blue Jays (MLB).
Having grown up playing football through high school and still playing pick-up hockey games now, his other hobbies include real estate, keeping an eye on the stock market and going fishing. The caddie says he always carries his fishing rod when he's on the road and tries to get out as much as he can.
Little's dream fourball would include his father, former MLB star Josh Donaldson and Dallas Stars captain, Jamie Benn. Outside of golf, Little volunteers at the Boys and Girls Club in Plano/Frisco.
