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. According to Phil: The Rip-Roaring (and Unauthorized!) Biography by Alan Shipnuck, Bones ended the partnership with a formal letter. No blow-up, just a calm, classy exit after years of quiet tension. Why? Substantial unpaid back wages and more reasons.

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.

The split occurred just a few years after Mickelson’s name surfaced in the Billy Walters insider trading case, while his gambling debts were at their peak. 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. “Our decision is not based on a single incident. We just feel it’s the right time for change,” said Mickelson. Still, the rumors persisted: Mickelson allegedly owed Jim Mackay significant back pay. Neither side ever publicly denied. Then, Bones joined NBC and the Golf Channel as an on-course reporter before joining Justin Thomas in 2021. 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. But, “There’s really not,” he revealed. “Some of my closest friends, again, are players now.” 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 were just 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.

In the early days, caddies were often seen as simply bag carriers. Then, the role evolved into strategic advisors, sports psychologists, and emotional anchors. Bones was part of that evolution when he started caddying in 1990. He then became a trusted shot whisperer to Mickelson, especially during bold plays at Augusta. Over time, he’s long made it a point to celebrate the player-caddie connection, none more famously than at his annual Phoenix Open dinners.

Questions at Jim “Bones” Mackay’s legendary Phoenix Open dinner

Renowned for his 25-year tenure as Phil Mickelson’s caddie, Bones 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. Aside from dinners, he has organized walk-and-talk practice rounds, team-building efforts during U.S. team competitions, after-hours caddie hangouts—often at local pubs or low-key venues, and low-pressure meet-and-greets between broadcasters and players. But, one of his most cherished traditions was hosting annual dinners during the WM Phoenix Open week at his Scottsdale, Arizona home.

However, the atmosphere focused on comfort, storytelling, and laughter, the inclusivity of lesser-known players and caddies. A perfect gathering for foodies under pressure before big games. These gatherings served as opportunities for mentorship, relaxation, and, of course, feedback.

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 Phil: The Rip-Roaring (and Unauthorized!) Biography of Golf’s Most Colorful Superstar, Mickelson, failed to send these 18th-hole flags. Instead, he kept them for his late grandfather’s collection. Although respectful of the move, Mackay felt slighted. Eventually, Mickelson did send them, 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 symbolize 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.