Who Is Gary Woodland's Caddie?

Gary Woodland has had the same caddie for a while now, so we get to know Brennan Little a little better here.

Who Is Gary Woodland's Caddie?
(Image credit: Getty Images)

Who Is Gary Woodland's Caddie?

The man currently carrying American Gary Woodland's bag is Brennan Little. Little has been caddying since 1999 and just some of the other players he has teamed up with include Mike Weir, Sean O'Hair and Camillo Villegas.

mike weir caddie

Little with Weir in 2003 (Getty Images)

(Image credit: Getty Images)

Two of his finest career moments so far are helping Mike Weir to victory at the 2003 Masters and then guiding Woodland to victory at the 2019 US Open at Pebble Beach. In fact he is quite the player himself as he says he has a handicap of 2 and the man born in Canada also played collegiate golf at New Mexico State.

His favorite golfer growing up was Greg Norman and his favorite golf course to caddie at currently is Augusta National. That being said he also says his favorite Tour stop is Colonial because he knows the golf course well and it is close to his home. He currently resides in Dallas, Texas.

gary woodland caddie

(Image credit: Getty Images)

As mentioned above he was born in Ontario, Canada and as such he loves playing and watching ice-hockey. He says that his dream alternate career choice would be a general manager of a hockey team. He also makes sure he always carries a fishing rod whilst travelling and he tries to go fishing as often as he can when out on the road. As far as dream four-balls go, he says he would like to play with his Dad, MLB star Josh Donaldson, and NHL star Jamie Benn.

Outside of golf he has said he volunteers at the Boys and Girls Club in Plano/Frisco.

To see which clubs Little carries, read our Gary Woodland what's in the bag post, or learn more about Woodland's wife Gabby Woodland

Sam Tremlett
E-commerce Editor

A golfer for most of his life, Sam is a Senior Staff Writer for Golf Monthly. 

Working with golf gear and equipment over the last six years, Sam has quickly built outstanding knowledge and expertise on golf products ranging from drivers, to balls, to shoes. 

He combines this knowledge with a passion for helping golfers get the best gear for them, and as such Sam manages a team of writers that look to deliver the most accurate and informative reviews and buying advice. This is so the reader can find exactly what they are looking for.


Sam now spends most of his time testing and looking after golf gear content for the website, whilst he is also responsible for all content related to golf apparel. 

He also oversees all Tour player content as well so if you need to know what clubs Tiger or Rory has in play, Sam is the person to ask. 

Unfortunately, Sam is not a member of any club at the moment but regularly gets out on the golf course to keep up the facade of having a handicap of five. 


Sam's What's In The Bag: 

Driver: Titleist TS3 (9 degrees) 

Fairway Wood: Callaway Paradym (15 degrees), Nike Covert Tour 2.0 (19 degrees) 

Irons (4-PW): Titleist AP2 

Wedges: Titleist Vokey SM7 54˚, 58˚ 

Putter: Scotty Cameron Phantom X 5.5 

Ball: Srixon Z-Star Diamond

Shoes: G/FORE Gallivanter/Nike Air Zoom Infinity NEXT%/Cuater The Ringer