The conversation picks up on the Jon Gruden storyline with Evan laying out why, if the idea truly came from ownership, it would signal just how desperate the New York Jets might be. Evan argues that if Jon Gruden ever returns to coaching, it would take both money and real power, and the Jets might be the only team willing to hand him the keys to the franchise. The crew also discusses the unspoken reality that any team openly embracing Gruden could face quiet backlash from the rest of the league, even if fans never see it publicly.

From there, the phones flip the segment toward hockey and New York sports pride. Callers gush over Matthew Schaefer, with bold claims that he is already the new king of New York sports. Evan pushes back on the hype, agreeing Schaefer is special but cautioning against crowning dynasties after a few months, which turns into a heated back and forth about prospects, sure things, and why fans always protect their own guys.

The segment closes with a classic Knicks history argument as callers debate who really kept the New York Knicks from winning a championship in the 1990s. Evan breaks down why both Michael Jordan and Hakeem Olajuwon were roadblocks, but draws a clear distinction with LeBron James, arguing LeBron never haunted the Knicks the way Jordan did, and that the lingering resentment toward him says more about fan emotion than actual history.