Since Rory McIlroy hired best friend, Harry Diamond as his caddie in 2017, the pair have enjoyed plenty of success together - including two Players Championships, three Race To Dubai titles and a couple of Tour Championships.
They have both earned an eye-watering amount of money, too, and McIlroy's performances at the start of 2025 have seen that number grow at an exponential rate - to the brink of the $100 million mark on the PGA Tour career money list, at least.
While a number of strong finishes have obviously swollen the four-time Major winner's bank balance, there is a very good chance Diamond would have benefitted greatly as well.
Following the rest of his trade, the pro looper will either be on a retainer or an annual salary as a vital part of McIlroy's team. But the opportunity for an extra bump in Diamond's earnings arrives every time they enter an event.
The general consensus in men's pro golf is that caddies take a cut of 5-10% depending on how high up the leaderboard their player finishes. Should McIlroy win an event, then Diamond might well expect to receive 10% while a result inside the top-10 could result in a 7% bonus and outside that may see 5%. It is important to stress that the numbers in relation to Diamond's bonuses are educated predictions rather than bona fide facts.
Either way, McIlroy and his looper made a decent start to their season when the former finished T4th at the Dubai Desert Classic on the DP World Tour. The World No.2 collected prize money of roughly $437,000 and may well have passed just over $30,000 of that on to Diamond.
The Northern Irish duo then began their PGA Tour season in the best possible way via a victory at the Pebble-Beach Pro-Am - a Signature Event with a $20 million total prize purse. McIlroy banked a very healthy $3.6 million and - sticking to the common practice - would have theoretically shared $360,000 of that with his on-course assistant.
A couple of relatively-disappointing finishes for McIlroy thereafter - T17th at the Genesis Invitational and T15th at the Arnold Palmer Invitational - still saw Diamond earn an extra $31,000 or so as his boss bagged just over $620,000 across the fortnight.
The 28-time PGA Tour winner made up for it, however, after eventually seeing off JJ Spaun in a Monday playoff at TPC Sawgrass' Stadium Course to earn the $4.5 million top prize. Diamond, credited for some brilliant work on the bag during that week, was likely rewarded with a $450,000 check of his own.
As it stands, Diamond has possibly picked up around $870,000 so far this term. That figure is considerably higher than the PGA Tour average ($766,282) at this stage and more than big-name players like Jordan Spieth ($765,150), Wyndham Clark ($769,786) and Tom Kim ($833,185) have earned in 2025.
During 2024, the story was about Scottie Scheffler’s caddie Ted Scott and his earnings (it is estimated he may have won over $5 million on the World No.1's bag), but it is McIlroy’s looper in the money so far this year.
