“After 25 very rewarding and memorable years, Bones and I have mutually decided to end our player-caddie relationship.” Phil Mickelson used that statement in June 2017 to announce the end of a partnership that had defined his career. 

The press release praised Jim “Bones” Mackay’s preparation, decision-making, and loyalty across 25 years on Tour. Mackay issued his own message, describing his original goal of caddying in a Ryder Cup and noting that he stood alongside Mickelson for his eleventh appearance at Hazeltine in 2016. Both statements pointed to friendship between their families and wished each other success.

The public messaging framed the decision as mutual. Inside professional golf, the reaction differed from the official version. Mackay had already informed Mickelson three weeks earlier at the Memorial Tournament that he was leaving. Those familiar with the circumstances described a long period of unresolved disputes, with money at the center.

The press releases presented the separation as a mutual decision, but reaction inside professional golf differed from the public messaging. The partnership had already ended three weeks earlier at the Memorial Tournament. In his biography, Alan Shipnuck writes, “Bones actually fired Phil. He was owed $900,000,” referring to a decade of unpaid FedEx Cup bonus money that Mickelson had committed to sharing with his caddie. Those familiar with the situation described the financial issue as a longstanding source of tension that ultimately led Mackay to end the relationship.

By Mackay’s calculation, the outstanding amount reached approximately $900,000. In the months before the separation, Mickelson transferred $400,000 toward that figure. A second payment of $400,000 arrived a week after Mackay ended the partnership. Even after two payments totaling $800,000, Mackay believed Mickelson had not made him whole on the FedEx Cup bonus money.

Financial tension developed alongside differences in day-to-day working habits. Mackay had been increasingly concerned that his advice carried less influence during competitive rounds. He was also frustrated by Mickelson arriving at courses later than the times communicated to his caddie, affecting preparation. The disagreements extended into one of golf’s longstanding traditions. Winning caddies customarily keep the 18th-hole flag from each victory as a record of their career. 

Mickelson kept every flag during their 25 years together, beginning with the 2004 Masters, when he framed the flag and gave it to his grandmother shortly after his grandfather’s passing. Mackay respected that choice. 19 additional victories followed, including 4 major championships, and he did not receive a single flag.

The absence drew attention inside caddie circles. During the Phoenix Open, the Mackays hosted dinners for players and caddies, and the lack of flags became a recurring topic. Within that environment, the flag represents the caddie’s place in a shared victory. Those close to Mackay indicated that the issue affected him more than those outside the profession might expect.

After Mackay privately ended the partnership and expressed the reasons, Mickelson overnighted 4 major championship flags from the PGA Championship, the Open Championship and the 2006 and 2010 Masters, along with the second $400,000 payment. The flags included large signatures across the fabric. Mackay, according to those familiar with his view, believed the oversized autographs reduced their value as keepsakes. He has not displayed them and intends to sell them in the future and donate the proceeds to charity.

The remaining flags from their other victories stayed with Mickelson. Shipnuck’s reporting notes that Mickelson avoids signing golf balls publicly due to the difficulty of producing a clean signature, yet has signed dozens privately and stored them for his children. Those familiar with his approach believe the flags may hold similar value.

After the split, Mickelson assigned caddie duties to his brother, Tim Mickelson. Mackay did not comment beyond the official statement. The partnership closed after 25 years through a decision by the caddie rather than a mutual agreement, driven by unpaid compensation and actions he viewed as dismissive of his role in one of golf’s most successful careers.

Written by

Aditi Singh

Edited by

Joyita Das