Pablo Torre Finds Out What the Hell Happened to Phil Mickelson?
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Nov 18, 2025 
Alan Shipnuck, a veteran golf writer and author of the unauthorized biography 'Phil', dives deep into the tumultuous career of Phil Mickelson. They explore Mickelson's transformation into a culture warrior, fueled by a craving for risk and recognition. Shipnuck shares anecdotes of Mickelson's early charm and media savvy while dissecting his recent controversies, including heavy gambling and his divisive persona. The conversation reveals how Mickelson's choices shaped his legacy, leading from golfing greatness to public scrutiny.
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Overconfidence Explains Risky Choices
- Shipnuck describes Phil as undeniably bright but overconfident and prone to misjudgment when he must be the smartest person in the room.
- That personality explains repeated risky moves that often backfire despite occasional success.
Early Charm Built Media Cachet
- Alan Shipnuck recalls meeting Phil in 1994 when Phil introduced himself to a lowly Sports Illustrated intern and flattered him heavily.
- That early charm explains how Phil built media relationships that later complicated reporting on him.
Caddy Debt Damaged Relationships
- Shipnuck reports Phil owed his longtime caddie Jim "Bones" Mackay roughly $900,000 and delayed payment for years.
- Phil eventually sent checks totaling $800,000, leaving a bitter, unpaid remainder and damaging relationships.
