Harry Diamond: More Than Just a Caddie for Rory McIlroy
Harry Diamond isn’t your average caddie. He’s Rory McIlroy’s longtime friend, practically family, and has been by his side as caddie since 2017. Their friendship began back in Northern Ireland at Holywood Golf Club, where a seven-year-old McIlroy first met Diamond—who quickly became “like a big brother.”
Unlike many professional player-caddie relationships, theirs is built on decades of trust. And it’s paid off—literally and figuratively. In the world of professional golf, top caddies typically earn a base salary of $3,000–$4,000 per week, plus bonuses: 10% of winnings, 7% for top-10 finishes, and 5% for making cuts.
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So, when McIlroy clinched a dramatic playoff win at the 2025 Masters, Diamond reportedly earned a $420,000 bonus from McIlroy’s $4.2 million prize. With earlier wins in 2025 already netting him between $870,000–$900,000, Diamond is projected to top $1 million in earnings this year—making him one of the highest-paid caddies in the sport.
But Diamond’s value goes far beyond paychecks. A talented amateur golfer in his own right, he won the 2012 West of Ireland Championship and represented Ireland internationally. Before joining McIlroy full-time, he worked in his family’s hospitality business. Since becoming McIlroy’s full-time caddie—originally considered a short-term replacement for J.P. Fitzgerald—Diamond has proven his staying power.
His job involves far more than carrying clubs. He arrives early to tournaments to scout the course solo, assess conditions, and strategize. He knows McIlroy’s moods, strengths, and pressure points, which lets him offer exactly the right words at the right time. After McIlroy missed a short putt that could’ve sealed the Masters before the playoff, Diamond calmed him down with a simple but powerful reminder: “Well, Pal, we would have taken this on Monday morning.”
Their connection proved essential in navigating years of criticism—especially toward Diamond, who some believed lacked the technical skills of a “top-tier” caddie. But McIlroy has always defended him, valuing trust and loyalty just as much as yardage and pin positions.
Diamond was even the best man at McIlroy’s wedding, another sign of how intertwined their lives are. Their victory at Augusta wasn’t just a career-defining win; it was a deeply personal triumph that silenced doubters and reinforced their special bond.
A million-dollar caddie may sound extreme to some, but when that caddie brings a lifetime of trust, emotional intelligence, and unwavering support—it might just be worth every penny.