'I'm Holding Him To It' - Gary Woodland And Caddie To Swap Roles At Senior PGA Championship

Woodland's caddie Brennan Little qualified for the Senior PGA Championship at Congressional later this year, with the PGA Tour pro set to carry out looping duties

Gary Woodland (right) and his caddie, Brennan Little give a thumbs up to someone out of shot at the 2024 Zozo Championship
(Image credit: Getty Images)

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.

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."

Gary Woodland (right) and his caddie, Brennan Little point something out in the distance at the 2024 Zozo Championship

(Image credit: Getty Images)

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."

Gary Woodland looks down at the PGA Tour Courage Award in his right hand during his Cognizant Classic press conference

(Image credit: Getty Images)

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.”

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Jonny Leighfield
Staff Writer

Jonny Leighfield is our Staff News Writer who joined Golf Monthly just in time for the 2023 Solheim Cup and Ryder Cup. He graduated from the University of Brighton with a degree in Sport Journalism in 2017 and spent almost five years as the sole sports reporter at his local newspaper. During his time with Golf Monthly, Jonny has interviewed several stars of the game, including Robert MacIntyre, Ian Poulter, Lee Westwood, and Joaquin Niemann. An improving golfer himself, Jonny enjoys learning as much about the game as he can and recently reached his Handicap goal of 18 for the first time. He attended both the 150th and 151st Open Championships and dreams of attending The Masters one day.

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