Harry Diamond isn’t just any caddie. He’s McIlroy’s childhood friend from Northern Ireland who has been carrying his bag since 2017. Their connection runs deeper than most player-caddie relationships in professional golf. They first met when the Irish golfer was just seven years old at Holywood Golf Club, where Diamond became “like a big brother” to the future champion.
The standard arrangement for top caddies includes a weekly base salary plus performance bonuses. Diamond reportedly earns $3,000-$4,000 weekly regardless of tournament outcome. The real money comes from McIlroy’s success – 10% for wins, 7% for top-10 finishes, and 5% for making cuts.
So, when Rory McIlroy sank that dramatic playoff putt at Augusta National, his caddie Harry Diamond didn’t just celebrate a Masters victory; he also pocketed a staggering $420,000 bonus from McIlroy’s $4.2 million Masters victory. This adds to an already impressive 2025 for the caddie. Reports indicate he had earned between $870,000-$900,000 in bonuses from McIlroy’s earlier wins this year alone. His annual earnings likely approach or exceed $1 million, making him one of golf’s highest-paid caddies.
“To be able to share this with him after all the close calls we’ve had, all the crap that he’s had to take from people that don’t know anything about the game… this one is just as much his as it is mine,” McIlroy said after his Masters win about his bond with Diamond. Those emotions reflected the criticism Diamond has faced during their partnership. After the missed putt at the Pinehurst last year, Diamond was criticized a lot for his lack of skills, and McIlroy decided to tune it all out.
But what does carrying the bag for a champion like McIlroy involve? Beyond the paychecks, Diamond’s role demands dedication and a unique skill set.
Life on tour demands meticulous preparation and mental strength
Before joining McIlroy’s team, Diamond was an accomplished amateur golfer himself. He won the 2012 West of Ireland Championship and represented Ireland internationally. Rather than pursuing a playing career, Diamond worked in his family’s property business, managing hotels and restaurants in Belfast and Bangor.
Their relationship extends beyond the course. Diamond served as best man at McIlroy’s wedding to Erica Stoll. In 2017, he replaced McIlroy’s previous caddie, J.P. Fitzgerald, who had been with him since turning professional. Many considered it a temporary arrangement, but they’ve remained together ever since.
Diamond’s tournament routine reveals the demanding life of a top caddie. He typically arrives at venues a day before McIlroy to walk the course alone. This advanced preparation allows him to study layouts, analyze pin positions, and identify potential challenges.
He meticulously notes course conditions, green speeds, and strategic options. During competition rounds, Diamond maintains a calm demeanor that complements McIlroy’s more emotional approach. His communication style isn’t as vocal as other caddies, but his words carry weight at crucial moments.
After McIlroy missed a short putt that would have won the Masters outright, Diamond provided perfect perspective. “Well, Pal, we would have taken this on Monday morning,” he said simply. This straightforward encouragement helped McIlroy reset mentally before the playoff.
Diamond’s understanding of McIlroy’s personality comes from their decades-long friendship. He knows when to speak up and when to stay quiet. This emotional intelligence proves just as valuable as course knowledge in high-pressure situations.
Their Masters’ triumph represents more than just financial reward. It vindicates their partnership and friendship against years of doubt from outsiders. For Diamond, the $420,000 payday surely feels sweet, but helping his childhood friend complete the career Grand Slam? That’s truly priceless.
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