The Herd with Colin Cowherd
Best of The Herd — May 8, 2026
Guest Hosts: Israel Gutierrez, Stu Gotz, Taylor, Mike A.
Notable Guests: Sean McDonough, Jeff Passan
Episode Overview
This installment substitutes Colin Cowherd with a loose, energetic roundtable led by Israel Gutierrez, Stu Gotz, Taylor, and Mike A., broadcasting from multiple cities. The team flushes out top sports stories with humor and candor, tackling “ring culture,” the careers of Draymond Green vs. Charles Barkley, James Harden’s postseason legacy, MLB debates, and who truly shapes a franchise’s winning culture. Later, baseball insider Jeff Passan joins to dissect major Yankees prospects, the value of “fit” for legendary players, and share in the hosts’ free-flowing, raucous gamesmanship.
Key Discussion Points & Insights
1. Broadcast Tales, Throwback Vibes, and The "Right Place, Right Time" Question
- Setting & Vibe: Israel Gutierrez celebrates broadcasting from Syracuse’s fabled Newhouse School, trading self-deprecating jokes about being among Newhouse alumni legends like Sean McDonough, Marv Albert, and Iron Eagle.
- “Had I gone to a school like this, man, would I be good at broadcasting. Oh, my God. The facilities here." — Israel Gutierrez (03:39)
- Hosts reflect on their own radio journeys, referencing media legends and former radio slots (“10 to 1 is the best slot in radio”).
- Personal anecdotes about gym mishaps and wardrobe choices set a playful, relatable tone.
- "Signs" of Bad Days: The segment humorously explores locker room misadventures and how small mishaps (exploding water flossers, etc.) can set the tone.
2. Ring Culture, Draymond Green vs. Charles Barkley, and Legacy Debates
(10:05-18:47)
- The show pivots to the viral Draymond Green–Charles Barkley TNT segment, questioning the value of championships in defining legacy.
Key Quotes and Thoughts:
- [12:14] “Whose career would you rather have, Draymond Green's or Charles Barkley's?” — Israel Gutierrez
- [12:28] "Does Draymond Green seem happy to you?" — Stu Gotz
- [14:28] “Rings don't define who you are... Draymond Green is not going to be the next Charles Barkley of broadcasting, because those four rings aren’t going to make him entertaining.” — Stu Gotz
- Consensus emerges that mental satisfaction, individuality, and post-career achievements (Barkley's broadcasting success) mean more than “ring culture.”
- Taylor on Ring Culture: “Ring culture has gotten completely out of control…”
- Playful debates include whose career is preferable if you could choose, with the hosts generally siding with Barkley over Draymond, except Israel Gutierrez who briefly opts for Draymond’s four rings before conceding to Barkley as the more “complete” career.
3. The James Harden Postseason Paradox: More Turnovers than Buckets
(24:39-38:38)
- AI Colin on Cavs–Pistons series: “Detroit going up 2 zip on Cleveland tells you everything. This isn’t a cute story. It’s a power move.” (25:04)
- The panel lambasts James Harden’s continued postseason woes—his inefficiency becomes a stand-in for the pitfalls of stat-driven “regular season greatness.”
- Memorable Quotes & Stats:
- [26:17] "Can you think of a career highlight defensive play of James Harden?" — Stu Gotz
- [30:22] Taylor read a stat: “James Harden played his 182nd career playoff game tonight… his 46th playoff game with as many or more turnovers than made field goals. That’s over 25% of his career playoff games.”
- Ribbing on the “laughable debate” of Harden vs. Dwyane Wade as all-time 2-guard.
- Debates whether Harden, like Clayton Kershaw in MLB, is “playing his way out” of all-time great status.
- "We’re obsessed with scoring in a way that maybe we weren’t before… when you really break it down, if you really defend it hard during a seven-game series, it’s not going to be as effective." — Stu Gotz (32:27)
4. "Right Place, Right Time" Hall of Fame / Jeter Hypotheticals
(39:30-44:46)
- The panel tackles whether some Hall of Famers are “right place, right time” products.
- Debate Focus: Would Derek Jeter be as iconic if he played for the Pirates or Royals?
- [41:45] Taylor (sarcastic): “If Derek Jeter was a Pirate… Brian Giles would be Bernie Williams. David Wells? They had Kip Wells. He becomes the same thing.”
- [43:13] Israel Gutierrez: “Take Derek Jeter off the Yankees… it’s right place, right time, that’s all he was.”
- Pushback from Stu and Taylor insists Jeter’s greatness would’ve shone through almost anywhere, not just in New York.
- Comparison: “Do you agree, Scottie Pippen, right place, right time?” (43:31)
5. Baseball Deep Dive With Jeff Passan
(48:24-59:32)
- On the Scene: Jeff Passan joins from Syracuse, discussing:
- The burden and cost of sports broadcasting education.
- His ESPN podcast “Sources Tell Jeff Passan.”
- The grind of creating original audio content vs. live reporting: “It’s hard doing what you do. My job at ESPN is often reacting… doing a show like this is creating something... not something I’ve done before.” (50:19)
- Yankees Prospect Talk:
- Cam Schlitler, already pitching like a frontline ace, is compared to Paul Skenes.
- [52:47] “I think you were stupid before the season as well.” — Passan to Taylor’s ‘no’ on a Schlitler-for-Skenes trade.
- High hopes for Spencer Jones, but questions about contact rate: "If his plate discipline can get even better... we're talking about a perennial MVP candidate." (54:56)
- MLB’s Newfound Joy: Praise for elaborate dugout celebrations (Rockies’ faux fur coat, Blue Jays’ “flags” jacket).
6. Artificial Intelligence, Market Fit, and the Dodgers as MLB’s Villain
(62:47-67:39)
- AI Colin Analysis & Skepticism:
- AI Colin (in segment stingers) provides surprisingly nuanced takes on trades (e.g., Schlitler vs. Skenes), team-building, and the Dodgers as MLB’s “measuring stick.”
- "Let the Dodgers be great and let everybody else chase them. What’s bad for baseball is the dead weight... don’t spin, don’t develop, and don’t try." — AI Colin (65:56)
- Jeff Passan: “If we are leaning on AI for baseball analysis, then we have lost the plot, gentlemen.” (64:56)
- Hosts joke about the “future AI wars,” with some nervously claiming, “I am not on Jeff Passon’s side on this.”
7. "One Table" Game – Greatness, Cities, and Dinner Tables
(69:12-73:34)
- Hypothetical: If the all-time greats show up for dinner in their cities, who gets the only table?
- Maddox vs. Glavine vs. Smoltz (Braves): Maddox wins for skill and humor.
- Jeter vs. Judge (NY): “Derek Jeter always.” But “as a Pirate,” Judge would win!
- Votto vs. Rose (Cincy): Dead Pete Rose still gets the table.
- Koufax vs. Ohtani (LA): Passan reluctantly says today’s Ohtani would get it, but if it’s his restaurant, “I would see Sandy Koufax over goddamn himself.” (72:49)
Notable Quotes & Moments
- On Draymond Green:
“Draymond already reached the top four different times and is still unhappy.” — Stu Gotz (15:40)
“He's not going to be the next Charles Barkley of broadcasting, because those four rings aren’t going to make him entertaining.” — Stu Gotz (14:28)
- On Harden vs. Wade:
“Dwyane Wade impacted the games in ways that James Harden couldn’t… if my team is missing 17 consecutive three pointers… I, meaning Dwyane Wade, would have done something, whether it be a pump fake and get to the line, something to slow that down.” — Stu Gotz (27:11)
- On AI Colin:
“If we are leaning on AI for baseball analysis, then we have lost the plot, gentlemen.” — Jeff Passan (64:56)
- On Yankees Legends:
“If Derek Jeter was a Pirate… Brian Giles would be Bernie Williams.” — Taylor (41:22)
- On Modern Baseball:
"Baseball for so long was like the dry chicken breast of professional sports... now we've finally got some sabor. Some seasoning. Some flavor." — Jeff Passan (57:08)
- Maddox at the Table:
“Greg Maddux was the king of clubhouse poop jokes. That's who I want dining at my restaurant.” — Jeff Passan (69:42)
- On the Dodgers as a "Villain" Brand:
"When you've got a monster brand... it gives the sport a villain, a measuring stick, and a reason to watch on a random Tuesday night." — AI Colin (65:56)
- On Aging and Fitness:
“Welcome to my life. All of our lives.” (at the gym being least fit) — Israel Gutierrez (06:08)
Timestamps for Key Segments
- 03:39 – Reflections on Syracuse and legendary broadcasting halls
- 10:05-18:47 – Draymond Green, Charles Barkley legacy and “ring culture” debate
- 24:39-38:38 – Harden’s postseason failures and the myth of playoff transformations
- 39:30-44:46 – “Right place, right time” Hall of Fame: Jeter, Pippen, and hypothetical scenarios
- 48:24-62:30 – Jeff Passan joins: Yankees prospects, fit & legacy, dugout celebrations
- 62:47-67:39 – AI Colin, Dodgers’ impact on baseball, and AI’s growing sports role
- 69:12-73:34 – “One table”: Who gets the city’s restaurant table—debates across sports icons
Tone & Style
The episode is playful, irreverent, and obsessed with dissecting sports mythology. No take is too extreme, and every legend is fair game for debate. There’s an “inside baseball” feel—both literally and figuratively—appealing to informed fans but delivered with enough comedy and personality for mass appeal.
For Listeners Who Missed It
Even in Cowherd’s absence, the show remains a rollicking, high-energy blend of wit, analysis, and barroom-style debates, with memorable riffs on ring culture, player legacies, and why context (and city) matters as much as talent. Jeff Passan’s cameo strengthens the baseball focus, and the show’s lively games and AI-supported arguments showcase just how fluid and fun big sports conversations can be.
Skip references to commercials, intros, and outros — All content above covers the heart of the episode.
