Rory McIlroy won the 2025 Masters to complete his career Grand Slam and registered his first-ever win at Augusta National. This was McIlroy's first Major championship victory with Harry Diamond, who has been caddying for him since 2017.
Diamond is a childhood friend of McIlroy, and the duo have played junior golf together. Their first association as a player-caddie happened during the 2005 Irish Open, where Diamond was invited to caddie for the 16-year-old Rory McIlroy, and now the duo has won the 2025 Masters.
Flushing It, one of the most prominent names on X, shared a video from the 2005 Irish Open and showcased how life has come full circle. They captioned it:
"Love this footage of 16-year-old Rory McIlroy at the 2005 Irish Open as an amateur. His good friend Harry Diamond was on his bag, and they just won the Masters together to complete Rory’s career slam. Amazing how these things come full circle."
This was the only instance when Diamond caddied for McIlroy as the Northern Irish golfer took JP Fitzgerald on the bag since his debut on the PGA Tour. The duo continued for over eight years until 2017, after which the Northern Irish golfer roped in his childhood friend Harry Diamond, who continues to be with him to date.
"I was an only child, and Harry was a big brother. We’re very close. I love having him on the bag. I’m a different person. And I’m never going to give him sh** even if something goes wrong. It would not be worth it," McIlroy once said via Golf Monthly.
Along with golf and caddying, Harry Diamond was also his best man when McIlroy married Erica Stoll in 2017, showcasing their close relationship.
Rory McIlroy called out Harry Diamond's critics
Rory McIlroy faced plenty of criticism for having Harry Diamond on his bag and not any well-known entity. Some fans and experts believed McIlroy could have won more tournaments if he had someone else caddying for him.

However, the Northern Irish golfer lashed out at the critics and said they criticize him when things don't go his way, while they don't say anything when good things happen.
"Just because Harry is not as vocal or loud with his words as other caddies, it doesn’t mean that he doesn’t say anything and that he doesn’t do anything," McIlroy said via Bunkered. "These guys that criticize when things don’t go my way, they never say anything good when things do go my way."
Since joining forces in 2017, McIlroy and Diamond have won 14 PGA Tour events and one Major championship so far. Overall, the Northern Irish golfer has earned 29 PGA Tour and five Major championship trophies.