Podcast Summary: Pablo Torre Finds Out

Episode: What the Hell Happened to Phil Mickelson?

Date: November 18, 2025
Host: Pablo Torre (PT)
Guest: Alan Shipnuck (AS), Golf Journalist and Author of "Phil"

Main Theme & Purpose

This episode dives deep into the unraveling of Phil Mickelson—a once-beloved golf superstar whose public reputation has shifted dramatically due to high-profile scandals, alleged insider trading, feverish political alignment with Trump-era right-wing politics, and a polarizing online presence. Pablo Torre and author Alan Shipnuck explore Mickelson’s evolution (or devolution), his love for controversy and risk, and the consequences of always needing “juice” in every arena of his life, from golf to gambling to Twitter.

Key Discussion Points & Insights

1. The Internet Persona and Recent Scandals

• Pablo’s new “Phil” problem: After engaging with Mickelson on social media regarding a questionable oil pipeline investment, Pablo experiences firsthand the volatility and deflection that have defined Mickelson’s online persona in recent years.
• Phil’s defamatory tweets: On Nov. 22, 2023, Mickelson publicly labeled Shipnuck “the worst liar and a pathetic human” (03:42). Shipnuck notes if there had been grounds for libel, Mickelson could have pursued legal action—which he hasn’t, reinforcing Shipnuck's reporting.

2. Who Is Phil, Really? – Nuance and Transformation

• Complexity over caricature: Rather than a one-dimensional villain, Shipnuck presents Mickelson as a nuanced figure—once admired for his charity work, charisma, and random acts of kindness (06:55).
• Political shift: Shipnuck notes that Phil “voted for Obama” once, was “socially liberal, fiscally conservative”—but has veered toward Trumpian performance in recent years (07:54).
• Perpetual edge-seeker: “He is always working an edge… and sets himself on fire. But sometimes, maybe it works out," says Shipnuck (08:33).

3. Phil’s Personality: Performer, Manipulator, Obsessive

• Charming early career: Shipnuck recounts unique access to Phil in the 1990s (11:18), lauding Mickelson’s charisma and relationship-building, especially with media and fans (14:50).
• Obsessiveness: Phil describes his “all-in” mentality (10:13), which applied to golf, learning, and, he feared, would apply to addictive behaviors.
• Philosophical contradictions: Throughout his career, Phil simultaneously chased approval, pushed boundaries, and maintained complex, sometimes adversarial media relations (16:16).

4. Scandals, Finances, and the Rise of ‘Juice’

• Conspicuous consumption and gambling losses:
  • Phil made “almost a hundred million dollars a year” at his peak (25:16), yet public complaints about California’s taxes exposed his lack of self-awareness.
  • Lavish spending—mansions, a G5 jet, exotic gifts like a T. Rex skull—paired with gambling losses approaching $100 million over 30 years (29:01).
• Caddie controversy: Underpaid longtime caddie “Bones” by nearly $900,000; paid him partial debt only at the end of their partnership, raising questions about Phil’s cash flow and motivations (29:34).

5. The LIV Golf Saga & Insider Trading

• Professional reformer? Shipnuck explains Phil’s decades-long push for PGA Tour reform—culminating in his role with Saudi-backed LIV Golf (31:31).
• Calculated risks: Mickelson played “both sides of the street,” negotiating with both the PGA Tour and LIV, always seeking leverage and validation for his “smarts” (32:58, 33:56).
• ‘The Juice’ Motivation: Contemporary Stewart Cink calls Phil “the ultimate juice guy.” Shipnuck: “It’s not even about the money, it’s about the adrenaline … like he just needs the juice” (35:24).
• Reckless activity: From insider trading allegations to offshore deals, Phil repeatedly risks everything for the thrill, not just financial reward.

6. Online Radicalization & Cultural Context

• Twitter transformation: Phil’s turn from media darling to bombastic internet troll mirrors other figures like Aaron Rodgers and Elon Musk (43:24).
• Personal pain: Shipnuck hints that personal/familial struggles with gender identity may have amplified Phil’s embrace of right-wing “culture war” talking points—drawing a striking parallel to Elon Musk’s public evolution (44:38).
• Siege mentality: Legal troubles, lost friends, and exclusion from social circles (notably after the Billy Walters scandal) contributed to Mickelson’s defensive, aggrieved public persona (44:38).

7. Legacy, Irony, and Final Paradoxes

• Vindicated on the merits, vilified for the method:
  • Despite being “right about a lot” regarding player power and compensation in golf, Phil "napalmed the bridges on his way,” ensuring he’d never be seen as a hero (50:17).
  • Squandered a natural post-retirement lap of honor due to his contrarian, self-destructive choices (52:34).
• The prophecy fulfilled: Pablo notes the ultimate irony—Phil was right that social media would be his undoing (53:24).

Notable Quotes & Memorable Moments

• “Every accusation is a confession. It’s a little Trumpian in that regard.”
  — Alan Shipnuck (03:31)

• “Phil is a once in a lifetime character for us in the sports media. He loves to talk. … Undeniably a bright guy, but he’s not as smart as he thinks he is. And that’s how he gets himself in these situations.”
  — Alan Shipnuck (06:05)

• "He just loves to pretend he knows everything. … He’s always working an edge."
  — Alan Shipnuck (08:33)

• "Do you remember the first time you got quality time with Phil Mickelson?"
  — Pablo Torre (10:38)
  “How many superstars in a sport are going to go up and introduce themselves to an intern?”
  — Alan Shipnuck (11:59)

• “Phil was a star before he even got to the PGA Tour. He was Tiger Woods before Tiger Woods arrived.”
  — Alan Shipnuck (13:09)

• “Everything about Phil is just funny. I mean, until it’s not.”
  — Alan Shipnuck (24:39)

• “Phil had all these huge deals. So he’s probably earned easily a billion dollars now… but he had a very high burn rate.”
  — Alan Shipnuck (25:16)

• “[Phil] needs the juice. And everything he does... Vegas. That’s why Phil’s so into gambling… it's about the juice.”
  — Alan Shipnuck (35:24)

• “I think there’s been this conformity of thought [on LIV golf]... especially the first couple years, anything goes. The players started speaking more freely… Phil already had those feelings… and just let it rip.”
  — Alan Shipnuck (40:26)

• “I think there’s a sadness there… a siege mentality. That joyfulness… just got extinguished, and now he’s under siege again.”
  — Alan Shipnuck (44:38)

• “He gave it all up because he had to be the smartest guy in the room and he had to reinvent professional golf in his image. And now he’s a pariah. … It's an incredible own goal. But in his mind, he was right about everything and it was worth it. And that's the ultimate paradox of Phil.”
  — Alan Shipnuck (52:34)

Timestamps for Important Segments

• [03:42] Mickelson’s insult: “Alan is the worst liar and a pathetic human.”
• [06:05] Shipnuck on Phil’s need to be the smartest guy in the room.
• [10:13] Phil on obsessiveness and why he avoids drugs.
• [13:09] Early stardom: Phil as Tiger before Tiger.
• [24:39] “Everything about Phil is funny. Until it’s not.”
• [25:16] Breakdown of Phil’s earnings and spending habits.
• [29:01] Gambling losses—close to $100 million.
• [31:31] Move to LIV Golf: motives and leverage.
• [35:24] The “juice”—risk as Phil’s real addiction.
• [40:26] The political transformation and influence of LIV Golf/Trump.
• [44:38] Siege mentality; parallels to Elon Musk and personal struggles inflaming politics.
• [47:54] Social media contradictions: “I don’t know who you are” and absurd denials.
• [50:17] Phil was right about golf reform but ruined his legacy by “napalming bridges.”
• [52:34] The ultimate squander: could have retired a hero, instead is a pariah.
• [53:24] Phil’s prophecy fulfilled: “He was absolutely right about what would happen if he logged on to social media.”

Final Thoughts

Through Alan Shipnuck’s reporting and Pablo Torre’s analysis, we learn that Phil Mickelson is a man defined by performance, craving validation, volatility, and risk—but also self-inflicted sabotage. His hunger for attention and “juice” drove both his sporting triumphs and personal downfalls. Despite some vindication for his critiques of the golf establishment, his methods burned every bridge, leaving him a pariah and online troll—a cautionary tale about genius undermined by ego and the irresistible lure of controversy.

For further exploration, check out Pablo Torre Finds Out wherever you get your podcasts.