Ever wondered who’s the guy by Rory McIlroy’s side at every big tournament? That’s Harry Diamond—his longtime friend turned full-time caddie. They grew up playing golf together in Northern Ireland, and when the Northern Irishman needed a new caddie in 2017, Harry stepped in.
What started as a temporary gig turned into a winning partnership, with multiple PGA Tour titles and deep trust between them. Off the course, Harry lives a quiet, private life and was even McIlroy’s best man! With nearly $900K earned in 2025 alone, this looper is living proof that friendship can lead to fairway success.
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