The Lovable Reunion - Joe Maddon on Rizzo's hangover, Cubs CRAZY pizza party & NEW 2016 World Series stories w/ David Ross
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In this emotionally rich and insightful episode of 'The Herd with Colin Cowherd,' former Cubs manager Joe Maddon reflects on his transformative 2016 World Series championship run, offering a masterclass in human-centered leadership. Maddon shares behind-the-scenes stories that reveal the culture of trust, celebration, and authenticity he cultivated—ranging from spontaneous pizza parties and Halloween costumes on the team bus to the iconic 'Embrace the Target' mindset that turned pressure into motivation. He highlights pivotal decisions, such as trusting David Ross to handle Johnny Cueto in a crucial inning and leaving Kyle Hendricks in Game 6, underscoring the balance between analytics and intuition. The conversation deepens with personal moments, including Ross wearing his father’s hat during a rain delay—a gesture that symbolized legacy and emotional grounding. These stories illustrate how mental resilience, player autonomy, and genuine connection were central to transforming a 'lovable loser' franchise into champions. The episode culminates in a touching exchange between Maddon and David Ross, where both emphasize the enduring power of authenticity, integrity, and staying true to oneself in the face of external pressures. Their reflections resonate beyond sports, offering timeless lessons in leadership and personal identity.
Trust and relationship-building precede strategy—build trust first, then exchange ideas.
Freedom off the field breeds respect and discipline on it: 'The more freedom given, the greater respect and discipline returned.'
Culture is built through celebration, not just winning—post-game parties and rituals kept the team mentally healthy.
Authenticity is the foundation of leadership: Stay true to who you are, even when surrounded by influencers and trends.
Simplify the process: Less information, fewer people, and status quo reduce mental and physical fatigue during high-pressure moments.
…and 3 more takeaways available in PodZeus
Introduction and the Rise of a Culture Builder
“I remember that so well just getting there in the first place. I really didn't have any Cub tradition built into me. I was an American leaguer.”
The Foundation of Trust and Culture
“You can't start with data, booklets, choreographed work. You start by relationship building, listening to people.”
The 2016 Championship Journey and Key Moments
“The sky's the limit when you're losing. You just throw everything out there.”
Leadership, Legacy, and the Human Element
Maddon reflects on his broader philosophy of leadership, emphasizing the balance between data and intuition. He shares his 'five levels of a big league player' concept, explaining how players evolve from 'happy to be here' to 'all they want to do is win.' He discusses the mental toll of daily competition and the need for pressure release valves like pizza parties and post-game celebrations. The chapter closes with his belief in honesty, transparency, and the power of the 'sharp knife'—direct truth that heals faster than lies.
The 2016 World Series: Process, Preparation, and the Power of Normalcy
“I didn't just BP. I didn't take BP one time in the World Series. Because I didn't want to go out to the soap opera, the media circus.”
“My dad passed in 2002. So he died on April 15, 2002. So we're the Angels in the World Series in 2002. I had his hat in my backpack which I took to every ballpark.”
“Authenticity cannot be manufactured. It's got to be organic.”
“Honesty without compassion equals cruelty.”
Host
Guests
Joe Maddon
person
David Ross
person
2016 World Series
other
iHeartRadio
other
Javy Báez
person
Jake Arrieta
person
Embrace the Target
other
Kyle Hendricks
person
Theo Epstein
person
Wrigley Field
place
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