Rory McIlroy’s crowning moment at Augusta—Shared with his childhood best friend.
Rory McIlroy made history at Augusta by completing the career Grand Slam, but it was his bond with lifelong friend Harry Diamond that made the moment unforgettable.
After a nerve-racking playoff with Justin Rose, McIlroy finally won the Masters, becoming just the sixth man in golf history to complete the career Grand Slam. But for those watching closely, it wasn’t just about the green jacket. It was about something deeper.
The first man to embrace McIlroy was Harry Diamond, his caddie, but more importantly, his boyhood friend from Holywood Golf Club in Northern Ireland. The man who stood beside him through the highs, the collapses, the pressure. The man who knew Rory before Rory was Rory.
This wasn’t just a sporting achievement. It was a shared journey. And it sticks out to me as one of the best parts of Rory’s success.
McIlroy’s talent has never been in doubt. By 25, he’d already won four majors, two PGA Championships, one U.S. Open, and The Open Championship. But the Masters? That was the missing piece.
He came painfully close in 2011, leading by four strokes heading into Sunday, only to fall away in the final round. “I’ll have plenty more chances,” he said back then. That was 14 years ago.
Since then, McIlroy has carried the burden of expectation, often playing well at Augusta, but never quite sealing the deal. Between 2015 and 2020, he had five top-10 finishes but no green jacket. The story became almost mythic: Rory, the nearly man at the Masters.
In 2017, McIlroy made a decision that changed everything. He parted ways with J.P. Fitzgerald, the caddie who had been on the bag for all four of his majors, and handed the job to his best mate, Harry Diamond.
Diamond, a solid amateur golfer himself, had no professional caddie experience. Many in the golf world raised their eyebrows. This was Rory McIlroy, one of the most marketable names in the game, entrusting his career to someone without a résumé in Tour pressure.
But Diamond wasn’t just any friend. He’d known Rory since they were kids at Holywood. He’d been best man at his wedding. He knew the golfer, but more importantly, he knew the person.
Over time, the results began to speak. McIlroy didn’t win another major immediately, but his form remained consistent. Diamond was calm under pressure, known for his quiet manner and sharp golfing brain.
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McIlroy entered this year’s Masters in good form, having already won twice on the PGA Tour earlier in the season. For me, it felt going into the tournament that this could be the one, but that did come with hesitation of course. McIlroy played with focus and restraint all week, making birdies without fireworks, playing with a kind of inner calm. He was in a great position going into Sunday, but as ever with Rory, it wasn’t going to come easy.
A double bogey on the opening hole. A ball in the water at 13. The ghosts of Augusta were back. Justin Rose’s final-round 66 forced a playoff.
But McIlroy, with Diamond at his side, didn’t blink.
On the second playoff hole, Rory stuck his approach to just a few feet. Birdie. Game over. Career Grand Slam complete. As the crowd erupted, McIlroy turned to Harry.
After the win, McIlroy’s voice cracked when talking about his caddie. “I’ve known Harry since I was seven years old,” he told the press. “To be able to share this with him, after all the close calls we’ve had, all the crap he’s taken from people who don’t know anything about the game—this one is just as much his as it is mine.”
It was an emotional release, not just for Rory, but for anyone who’s ever leaned on a friend through failure and stuck with them long enough to see it turn to triumph.
Harry Diamond never courted the spotlight. He never tried to be a brand. But in that moment, he was a central figure in one of sport’s greatest achievements, not because he carried clubs, but because he carried belief.
The relationship between golfer and caddie is often transactional. Some pros switch caddies like they change putters, seeking an edge, a spark, a fix.
But McIlroy’s faith in Diamond has never wavered. Even when critics said he needed a more experienced voice. Even when he went another year without a major. Even when the doubts were loud.
Their story is one of loyalty in a sport that often rewards short-term thinking. Of emotional intelligence over analytics. Of friendship over formula.
With this win, McIlroy enters golf’s rarest club, and Diamond can proudly own his part in that history. Rory may be the only one with the green jacket, but the journey, the years of hurt, pressure, and expectation, were certainly not walked alone.
In an era of data-driven coaching teams and media-trained entourages, Rory and Harry’s bond is a reminder that even with all the modern influences, you can’t replace the support of a solid human connection.
And maybe that’s what made this Masters win feel different. It wasn’t just about greatness. It was about goodness. About sticking with the people who know you best and letting them walk with you all the way to history.
Thanks for reading, David Skilling.
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