PGA Tour pro, Gary Woodland his caddie, Brennan Little are set to swap places later this year as the looper makes his Senior Major debut as a player.
Highlighted by his recent achievement, Little - who now lives in Plano, Texas - is an excellent golfer as well as being a top caddie, with seven career victories in the PGA of America's Northern Texas section. Last year, the Canadian-born looper won three of his five starts.
Continuing that form, the 55-year-old qualified for May's Senior PGA Championship at Congressional Country Club after coming through his local section and then doing enough at the National Club Pro stage in Oregon - despite a nervy finish.
The plan now, as far as the duo are concerned, is for Woodland to compete at the 2025 PGA Championship (Quail Hollow) between May 15-18 before taking the caddie bib off of Little a week later as they travel to Bethesda in Maryland.
The former New Mexico State player - who held a Handicap Index of around two in 2019 - revealed how the decision came about during an on-course interview with Golf Channel's Damon Hack at the Cognizant Classic.
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
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."
Little, a professional caddie himself since 1999, has been a part of two Major-winning performances as well as multiple other tour triumphs throughout his career. The first notable success was on the bag of Canada's Mike Weir at the 2003 Masters while the second arrived at the 2019 US Open alongside his current boss.
While those two victories came about as a result of professional excellent on both sides of the team, Woodland admitted his prowess as a looper is not quite to the same level as his playing abilities.
Responding to a question about the extent of his caddying history, the Kansas-born pro said: "It's very slim. Roles are going to be reversed, we're going to struggle a little bit considering Butchy does everything for me out here - I just hit the shots.
"I'm going to have to learn really quickly how to do everything. But I'm really proud of him, it was pretty cool what he did, and I'm excited to be there."
Earlier in the week, Woodland was announced as the PGA Tour Courage Award winner for 2025 as a result of his return to the professional game following brain surgery in 2023.
Despite the successful operation on the benign tumor, the 40-year-old has endured a difficult road to recovery involving serious mental-health battles which Woodland still fights to this day.
But, speaking in his pre-tournament press conference where he was announced as the award winner, an emotional Woodland vowed to continue "fighting for my dreams."
He said: “At the end of the day, I’m fighting. The last thing I’m going to let this do is let this thing in my head stop my dreams, and that’s why I fight every day. I want to be there for my kids and my family, but I want to chase my dreams, too. I’ve got a lot of dreams out here.
“I’m starting to understand what I need to do every day to function in life, but the things I’m doing to help with my brain are also helping me play golf, and I’m knocking on the door.
"I know my game is close. It’s coming, and I’m going to keep knocking on that door until I bust through, and then we’ll see what happens.”
