Little, who earned a weekly salary from Weir, then 32, also earned a share of all his winnings. This is a common arrangement, with percentages varying between pairs.
A caddy can receive a base of $2,000 (£1,580) per week, with 7% of their player’s winnings rising up to 10% to finish top of the leaderboard. If a season goes well, a cadet could earn a bonus.
However, most caddies cover their own expenses, which, when traveling around the world, can quickly add up.
When times are good and the million dollar checks are split, both parties are happy. But when times get tough and money dwindles, a golfer may feel like a hole in his pocket is the only thing his caddy can offer him.
Overall, even best friends can get fired.
“It’s all part of the business,” Little says. “You’re probably going to get fired and you’re also going to leave a player and get a better job.
“Sometimes change is a good thing; guys can just flat out. They can kick out their caddy and say, ‘We’re still good friends but I need to make a change to mix something up.’
Weir and Little worked together for 11 years until 2010 before Little took on a new challenge with Colombian Camilo Villegas.
There were no hard feelings between Weir and Little, but rather a mutual agreement to try something new.
Little now works with American Gary Woodland, the duo having won the 2019 US Open together.
In golf, both the caddy and the player can benefit from teamwork. In 2023, Little spent time with England’s Justin Rose in the run-up to the Open.
“It was interesting to see how it works,” Little says. “It’s totally different. It’s good to see his routines – when you’re with one guy you only see the same thing.
“I would even encourage it – if Gary had a buddy to play with him, that would be perfect for me.
“It helps him clear his head. If you have a guy who relies on you too much as a cadet, he doesn’t think for himself.”
The one constant on tour as a caddy is the community. Bits of local know-how about the course and its set-up are often shared.
At last year’s Masters, Brooks Koepka’s Northern Ireland caddy Ricky Elliott was cleared of revealing to Little, in violation of the rules of golf,, external which club Koepka had used to shoot.
Although cadets are not allowed to exchange advice mid-course, they often walk the course together before competitions to discuss strategy.
“Sometimes it’s good to just talk to the guys and see what they think about a hole and whether I agree or not – it doesn’t matter,” Little says.
“It’s good to have different opinions.”
Taneka Mackey is part of this community of caddies. She carries Amy Olson’s bag during the Ladies Professional Golf Association Tour (LPGA). Like Little, she fell into the role.
Growing up in the Bahamas and playing on their national golf team, Mackey always had a passion for travel. After getting the chance to help Olson at an event in the Bahamas in 2017, she saw the possibility of a career that would take her around the world.
“Amy said, ‘I still want you to caddy for me, can you come to Australia?’ When I heard the word Australia, I knew I had to get in shape and learn a few more things,” says Mackey.