Leaving Phil Mickelson Over Alleged Financial Disputes, Ex-Caddie Admits How Loopers Are Really Treated by Pros

Phil Mickelson‘s former caddie spent 25+ years alongside him, helping with five major wins, including three green jackets at Augusta. But in 2017, the famous player-caddie duo shockingly split, with whispers of financial disputes swirling around. Publicly, Mickelson called him “one of the most knowledgeable and dedicated caddies in the world,” and expressed “deepest respect, loyalty and admiration” for him. Behind the scenes, though, the split may not have been quite so clean. According to Phil: The Rip-Roaring (and Unauthorized!) Biography of Golf’s Most Colorful Superstar by Alan Shipnuck, financial tensions had built up over time.

Shipnuck reported that Mickelson’s caddie at the time, Jim “Bones” Mackay, actually “fired” Mickelson after years of simmering frustrations, with substantial unpaid back wages playing a major role. Mickelson’s massive gambling losses—estimated to be around $40 million between 2011 and 2014—may have only made the financial situation worse, fueling the rift between the two.

Mickelson later said in a statement: “Our decision is not based on a single incident. We just feel it’s the right time for change.” Still, the rumors persisted: Mickelson allegedly owed Jim Mackay significant back pay, something neither side ever publicly confirmed or fully denied. Now, in 2025, Mackay hopped on the Glue Guys Podcast and pulled the curtain back—not to air dirty laundry, but to reveal something deeper about life inside the ropes. And honestly? It’s not what a lot of people expected.

Reflecting on his career, Mackay admitted, “When I started in 1990, I never would have guessed that you would forge as many close relationships with the players as you ultimately do.” He explained that, at first, he assumed there would always be a divide between players and caddies. “There’s really not,” he revealed. “Some of my closest friends, again, are players now.” It’s not just a work relationship, either. According to Bones, invitations to players’ homes for dinners, weddings, and even golf trips are common. “I’ve been on golf trips with Phil to Ireland and Scotland and places like that,” he shared, highlighting just how personal many of these bonds became.

Mackay also talked about the special camaraderie during tournament weeks. Living in Phoenix for years, he organized a yearly dinner around the Waste Management Phoenix Open. “You’d invite 40 people, and 20 of them would come over—20 players, 20 caddies—and you’d just have an absolute ball,” he recalled. These weren’t just business dinners; they were casual, friendly hangouts where the line between player and caddie disappeared. Throughout the conversation, Mackay’s admiration for the players’ inclusivity shone through. “I’ve always been very impressed by how welcoming and friendly the players are to the caddies, and how inclusive they are in terms of what goes on,” he said.

Bones’ reflections show a side of professional golf that fans don’t often get to see. Even with the occasional financial dispute or professional split, the respect and relationships between players and caddies run deep. It’s clear that even after parting ways with Mickelson, Mackay’s admiration for the bond between players and caddies hasn’t wavered. He’s long made it a point to celebrate that connection, none more famously than at his annual Phoenix Open dinners.

Jim “Bones” Mackay’s legendary Phoenix Open dinners

Mackay, renowned for his 25-year tenure as Phil Mickelson’s caddie, has always been about more than just the game. Off the greens, Mackay worked tirelessly to foster a sense of community within the golf world, and one of his most cherished traditions was hosting annual dinners during the WM Phoenix Open week at his Scottsdale, Arizona home. These gatherings brought together both players and caddies, solidifying friendships and offering a rare opportunity for the golf community to unwind.

However, these dinners were more than just fun and food. A recurring question from guests was: “Where are the flags?” This referred to the tournament flags from Mickelson’s major victories, which, as per tradition, were typically passed on to Mackay. According to Alan Shipnuck’s biography Phil: The Rip-Roaring (and Unauthorized!) Biography of Golf’s Most Colorful Superstar, Mickelson, had failed to send these flags, a move that Mackay viewed as a breach of respect. Eventually, Mickelson did send the flags, but with large autographs that Mackay felt ruined their appearance. As a result, he chose not to display them and even considered auctioning them for charity.

Despite these issues, Mackay’s dinners remain a symbol of his dedication to personal connections in golf. These dinners were about camaraderie and friendship, a reminder that despite the intense pressure of professional golf, players and caddies share a bond that transcends the competition.

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