Podcast Summary: The Herd with Colin Cowherd

Episode: 3 & Out - Maxx Crosby to the Ravens, Eagles Questions, Kelce’s Future & NFL Contract Boom

Host: John Middlekoff
Date: March 9, 2026

Episode Overview

This episode is a deep-dive into another chaotic NFL offseason, with John Middlekoff focusing on several breaking stories: the blockbuster Maxx Crosby trade to the Baltimore Ravens, the implications for the Raiders and Ravens, swirling rumors about Jalen Carter’s future with the Eagles, big questions around Travis Kelce’s next move, and trends in NFL contracts and free agency. Middlekoff mixes league insight with his trademark directness, taking listeners through both the emotional and strategic sides of team-building in the modern NFL.

Key Discussion Points & Insights

1. Maxx Crosby Traded to the Ravens

[01:52–21:10]

• Blockbuster Deal Breakdown:

  • The Raiders send Maxx Crosby to the Ravens for a highly valuable haul: pick #14 and a 2027 first-rounder.
  • This is more than what the Cowboys got for trading Micah Parsons.
  • Notable that the Ravens, historically conservative, have never traded a first-round pick for a player before.

• Crosby’s Raider Legacy:

  • Middlekoff empathizes with Raider fans, painting Crosby as a Hall of Fame-level player with rare loyalty and effort.
  • “His 10 to 12 minute goodbye is one of the cooler, more genuine things I’ve ever seen.” – John Middlekoff [03:00]
  • Contrasts Crosby’s all-in attitude with previous Raider stars like Khalil Mack and Amari Cooper.
  • “Max Crosby represents what every coach really values in a guy whose effort is just great all the time.” [06:24]
  • Praises Crosby’s turnaround story—rehab after his rookie year, then total dominance for “mostly an awful organization.”

• The Trade Value & Strategy:

  • The Raiders land valuable draft capital—#1 and #14 overall picks in the same draft.
  • “Warren Sharp tweeted this out… this is the most draft capital a team ever had.” [13:05]
  • This move is setting up new GM John Spytack for a pivotal draft; pressure is high to make these picks count or risk repeating past failures (e.g. Khalil Mack/Amari Cooper trade drafts).

• Ravens’ New Aggression:

  • A departure from tradition as the Ravens swing for the fences, possibly setting a Super Bowl-or-bust expectation window.
  • “Their owner put his you-know-what on the table…. Let’s stop being so goddamn conservative.” [16:15]
  • The AFC powerhouses (Bills, Ravens) are now fully “all in,” as Middlekoff notes both teams are living in the short window and “living in the now.” [20:33]

2. Raiders’ Pressure to Execute on Draft Picks

[25:23–28:45]

• Cautionary tales: Previous failed drafts after big trades (referencing Clelin Ferrell, Damon Arnette).
• Importance of “nailing the pick” at #14 to reshape the franchise’s direction: “It all comes down to nailing pick 14. Do you get a Pro Bowl-level guy, or just an OK starter?” [26:54]
• Potential upside if things break right: combination of Mendoza, Bowers, Gentry, and more could lead to a much stronger roster in 2–3 years.

3. Jalen Carter/Eagles Trade Rumors

[28:46–33:50]

• Analysis of the Eagles’ extension for Jordan Davis, which Middlekoff reads as a signal they’re not comfortable paying Jalen Carter.
• Reports of teams calling about Carter; Middlekoff’s blunt advice:
  • “If you are an opposing GM and you’re talking to Howie Roseman on the phone about Jalen Carter—hang up the phone.” [30:20]
  • Eagles’ history: If they love you, they pay you; if they contemplate moving you, red flag.
  • The infrastructure around Carter is unique (connection to Georgia, support system), and outside of Philly, there’s concern about his fit.
  • Concludes the Eagles offloading Carter for a haul would cement Howie Roseman as an all-time GM.

4. Travis Kelce’s Uncertain Future

[33:50–38:36]

• Kelce enters free agency for the first time, with real uncertainty about whether he will remain with the Chiefs.
• “Most people do not go out like John Elway… It’s very rare for a guy to just run it out.” [34:25]
• Middlekoff predicts the New York Giants as the most likely destination if Kelce leaves Kansas City. Factors:
  • Giants’ young core, need for championship-caliber leadership,
  • OC/Nagy’s prior relationship with Kelce,
  • Market appeal (also referencing Taylor Swift).
• On KC’s approach: Rather than making a real offer, likely to “almost not even offer him a contract,” respecting his legacy but moving on.
• Old players changing scenery can rejuvenate careers: “It sparks a fire of creativity, of passion, of just, like, ambition.” [37:05]
• The limited crop of true impact free agents this year: Kelce stands out, but the class is thin with names like Daniel Jones listed in the top five.

5. NFL Contract Boom & Market Dynamics

[42:18–49:46]

• NFL paydays for non-QBs catching up:
  • Khalil Mack’s career earnings (~$220M) now eclipse JJ Watt ($130M), reflecting the jump in contract values at premium positions, especially edge rusher.
  • Maxx Crosby, still only 28, could reach $250M if he maintains current performance.
• Comparison with NBA and MLB—NFL stars are finally getting closer to those paydays, especially at key positions.
• Free agent market dynamics: Guards/centers are now far harder to draft and command big free agency contracts due to changes in the college game and spread offenses.
• On free agency price inflation:
  • “You typically have to pay a tax, a premium, to acquire a player in free agency, because you typically have multiple teams bidding on a guy’s services.” [45:05]
• On generational wealth and the complexity of inherited money:
  • Middlekoff’s personal reflection on the generational wealth narrative:
  • “You’re just gonna give your kids a bunch of free money?” [49:22]
  • Observations from Tom Brady about the difficulty in raising ‘normal’ kids in that context.

Notable Quotes & Memorable Moments

• On Maxx Crosby’s legacy:
  • “Max Crosby represents what every coach really values… effort is great all the time.” – John Middlekoff [06:24]
• On team-building pressure:
  • “It all comes down to nailing pick 14. Like, do you get a Pro Bowl-level guy or just get an okay starter? We’ll find out.” [26:54]
• On the Ravens’ boldness:
  • “Let’s stop being so goddamn conservative. We’re the Baltimore freaking Ravens. Let’s go for it.” [16:15]
• On the realities of the NFL:
  • “Most people do not go out like John Elway… Usually people play on another team. That’s the way sports work.” [34:25]
• On the free agency premium:
  • “You typically have to pay a tax… because you typically have multiple teams bidding on a guy’s services.” [45:05]
• On generational wealth:
  • “You’re just gonna give your kids a bunch of free money? It’s always, it’s like a little pet peeve of mine…” [49:22]

Timestamps for Important Segments

• Maxx Crosby Trade Overview & Raider Legacy: [01:52–13:50]
• Raiders Draft Capital & Team-Building Impact: [13:50–21:10]
• Pressure on Raiders to Use Draft Haul Well: [25:23–28:45]
• Jalen Carter / Eagles Trade Rumors: [28:46–33:50]
• Travis Kelce’s Free Agency & Future: [33:50–38:36]
• NFL Contract Trends / Salary Cap Discussion: [42:18–49:46]
• Philosophy on Generational Wealth: [49:46–52:46]

Tone and Style

Middlekoff blends passionate football analysis and personal anecdotes with blunt, direct language. He doesn’t shy from strong opinions or calling out NFL executives/players by name, but also brings moments of self-reflection (parenthood, personal pet peeves about the league, or wealth). His delivery is conversational, unfiltered, and accessible to both hardcore and casual NFL listeners.

For New Listeners

This episode is an excellent crash course on how a single trade can shape the league, why fans (and executives) place so much importance on draft picks, and the emotional realities for teams, players, and fans dealing with NFL’s perpetual churn. It also digs into big-picture issues about how money and opportunity are changing the game—and how legacies are made (or lost).

Tip: Use the timestamps to jump right to the segment that interests you most—be it the Crosby/Ravens deal, Eagles rumors, or the fascinating discussion on NFL contract trends.