Rory McIlroy did not win the 2025 Masters in regulation on 18, and he did not hide what it meant to him that Harry Diamond was still there when the chance slipped away. After McIlroy missed the putt that would have secured the green jacket, Diamond leaned into the moment on the ride back to the 18th tee and told him, “Hey pal, we would have taken a playoff at the start of the week.”
That line captured the relationship as clearly as any victory speech could. Diamond has been on McIlroy’s bag for nine years, and on Tuesday McIlroy said the caddie was “the big brother I never had.”
McIlroy and Diamond first met as kids on the putting green at Holywood Golf Club, with Diamond two years older than the golfer who would become one of the game’s biggest names. What began as a temporary arrangement after McIlroy fired JP Fitzgerald in 2017 eventually became permanent, even as Diamond was criticized at times as the reason McIlroy was not winning majors.
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McIlroy has long pushed back against that view by making the relationship personal, not professional. He and Diamond were best men in each other’s weddings, and when McIlroy was asked about him the night of the Masters, he got choked up. He said Diamond was the first person he looked at when he made the winning putt, adding, “I think that's what makes it so special.”
He said, “Harry's got a little brother and a big sister, so he had that.” Then he added, “But I always felt like Harry was my big brother.” For McIlroy, that is the part that still brings the emotion rushing back. “I think that's why, when I talk about it, that’s why it makes me emotional,” he said.
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The Masters left McIlroy with another major disappointment, but it also put his bond with Diamond in plain view. The questions now are about the next round, the next major, and whether the pair that grew up together in Holywood can finally turn that loyalty into the one trophy that has eluded them both for years.
