Podcast Summary: The Herd with Colin Cowherd

Episode: Derek Jeter joins The Herd

Date: October 28, 2025
Podcast: iHeartPodcasts and The Volume
Host: Colin Cowherd
Guest: Derek Jeter

Episode Overview

In this energetic and wide-ranging hour, Colin Cowherd is joined by legendary New York Yankees shortstop Derek Jeter. Their conversation dives into the nuances of postseason performance, the psychology and consistency of clutch athletes like Freddie Freeman, the changing nature of pitching in MLB, and the continued phenomenon of Shohei Ohtani. Jeter shares first-hand stories about what separates great players in October and reflects on his own career and the current Dodgers' postseason run. The segment finishes with Cowherd and Jeter discussing broader sports headlines, including NFL storylines and NBA breakout star Victor Wembanyama.

Key Discussion Points & Insights

Consistency & Clutch Performance in the Postseason

• Why Some Stars Thrive in October

  • Colin opens by comparing Derek Jeter's consistently high postseason stats to those of current stars like Freddie Freeman (03:00–04:27).

  • Jeter’s View:

    "I think it's more of a... just approaching every game like it's a regular season game. You pride yourself on consistency... it's the same approach when he's in the box, and that's what I appreciate about Freddie."
    — Derek Jeter (03:37)

  • Notable Quote:

    "I’m more surprised when [Freeman] doesn’t come through as opposed to when he does because you’ve seen him do it so much over and over and over. Regular season, postseason, it doesn’t matter."
    — Derek Jeter (03:58)

• Supporting Players Rising to the Moment

  • Discussion of players like Will Klein rising to unexpected roles (04:27–06:24).

  • Jeter relates how a strong clubhouse and experienced stars can “elevate” teammates:

    "When you’re with a group with a lot of experience and success... you don’t have to do too much yourself. You want to play your part, do your job. When you think small like that, good things happen."
    — Derek Jeter (05:38)

  • Jeter emphasizes that being surrounded by excellence allows role players to shine and “play [their] small part”—but applauds Klein for playing “more than a small part last night” (06:14).

Modern Pitching & the Ohtani Phenomenon

• Shohei Ohtani’s Two-Way Dominance

  • Jeter is in awe of Ohtani's ability to excel as both a pitcher and hitter (07:07–08:08).

    "He’s arguably the best offensive player in baseball... and pitching-wise... he could be the best pitcher in the game. It’s like he’s the 6’2” little leaguer that dominates, and he’s doing it at the major league level."
    — Derek Jeter (07:38)

  • Cowherd calls Ohtani possibly the greatest team sport athlete in American history (34:05).

• Bullpen Revolution vs. Workhorse Starters

  • Colin asks whether Jeter likes current bullpen-heavy postseason strategies versus relying on starters (08:08–09:50).

  • Jeter’s preference:

    "It's really a throwback... relying on your starters... it's fun to watch. The Dodgers are peaking at the right time from a health and pitching standpoint."
    — Derek Jeter (09:30)

    "[Bullpen games are] hard to do, especially in long series... the more times you see the bullpen, the better you’re going to be offensively.”
    — Derek Jeter (08:55)

The Psychology of Playoff Baseball

• Handling Adversity & Slumps

  • Colin addresses how players forget bad games or failures in high-leverage moments (15:26–16:20).

  • Jeter’s process:

    "When you get to the playoffs, only one thing matters. Every pitch, every at-bat, every situation, you have a chance to help the team win…I always found that it was easier."
    — Derek Jeter (16:20)

  • Jeter says he never dwelled on stats:

    "You don’t ever get in a box thinking about, what's my average this Series? It's, what can I do in this particular moment?"
    — Derek Jeter (16:40)

• Reflecting on His Own World Series Record

  • Colin points out Jeter’s World Series batting average (.321), better than even his career average (~.310):

    "That’s what you dream of…this is what fun is about…I just love it. If there’s one thing I do miss, if I could wake up and play in a World Series, I’d do it."
    — Derek Jeter (17:25–18:00)

The Value of Experience & Current World Series Outlook

• On Teams with Playoff History vs. Upstarts (Toronto / Dodgers)
  • Colin and Jeter discuss the edge that experience brings after dramatic, lengthy games (14:40–15:26).
  • Jeter warns:

    "I'd be very careful to count [Toronto] out... They have a very, very talented group that’s overcome adversity. But the Dodgers have the best team in baseball, playing well at the right time."
    — Derek Jeter (14:40)

Broader Sports Chatter (NFL, NBA)

• The segment includes a quick roundtable with Colin and J. Mack on upcoming NFL matchups (Ravens-Dolphins, Vikings-Lions) and a spirited breakdown of Victor Wembanyama’s breakout for the Spurs (23:06–24:26).
  • On Wemby:

    "I think Wembanyama— we're talking first team, All-NBA. That's how good. I mean, he's made such a freaking leap."
    — J. Mack (23:35)

Notable Quotes & Moments (With Timestamps)

• “I'm more surprised when he [Freeman] doesn’t come through as opposed to when he does.” — Jeter (03:58)
• “You just want to play your part... all I have to do is play my small part. But let me say this, [Will Klein] played more than a small part last night.” — Jeter (05:48)
• “[Ohtani] could be the best pitcher in the game.... It’s like he’s the 6’2” little leaguer that dominates, and he’s doing it at the major league level.” — Jeter (07:38)
• “You don’t ever get in a box thinking about, what's my average this Series? It's, what can I do in this particular moment?" — Jeter (16:40)
• "If there's one thing I do miss ... if I could wake up and play in a World Series, I'd do it.” — Jeter (17:55)
• “I'd be very careful to count [Toronto] out... But the Dodgers have the best team in baseball.” — Jeter (14:40)
• On the Dodgers’ current run: “This is the most talented baseball team of all time by far. Multiple guys throwing 100 miles an hour. International stars, power hitters, it's just..." — Cowherd (37:08)
• “We're all rooting for nine innings.” — Cowherd (18:24)

Timestamps for Important Segments

• [02:35] Intro to Derek Jeter and context of epic World Series games, discussion of clutch postseason play
• [03:37] Jeter on consistency and mindset in big games
• [04:27] How good players rise to the moment on star-studded teams
• [07:07] Derek Jeter on Ohtani’s two-way greatness
• [08:08] Debate on bullpen vs. starter pitching strategies in playoffs
• [14:40] Analysis of series advantage: Dodgers vs. Blue Jays
• [16:20] Jeter on managing postseason slumps and mental focus
• [17:16] Jeter recalls his World Series experience, reflects on what he misses about the game
• [23:06] Spurs and Victor Wembanyama NBA segment
• [34:05] Cowherd on Ohtani and the unprecedented global talent pool in MLB
• [37:08] The Dodgers’ talent and how surrounding cast elevates stars like Freddie Freeman

Tone and Energy

The conversation is friendly, insightful, and filled with mutual respect—Jeter brings calm candor and humility, while Colin mixes admiration with probing questions and trademark optimism about the spectacle of current sports. The episode is steeped in nostalgia, analytic perspective, and awe at the evolving landscape of modern athletics.

Summary Takeaways

• Derek Jeter’s legacy in October comes down to consistent mental preparation and not overinflating the moment.
• Teams with established stars give role players confidence to succeed in big moments.
• Shohei Ohtani is redefining what one player can do in baseball; even legends like Jeter are amazed.
• There is value in the traditional workhorse starter, but bullpen strategies remain vital in today’s game.
• The Dodgers’ current run, with high-end international talent and “household” clutch performers like Freeman, feels historic to both Cowherd and Jeter.
• Experience and mentality separate perennial champions from the rest.
• Playoff baseball’s drama is about living pitch-to-pitch, not stat-watching.

For anyone who missed the episode, this conversation between Colin Cowherd and Derek Jeter is essential listening for insights on what it takes to thrive on baseball’s biggest stage, reflections on the modern era’s athletic stars, and the enduring lessons of championship teams.