The Buffalo Bills know all about coming painfully close. Four Super Bowl losses in the 90s. Playoff exits that still haunt Orchard Park. Josh Allen has been slinging lasers since 2018. Sean McDermott‘s been steering the ship since 2017. Together, they’ve brought stability to a franchise that desperately needed it. But stability isn’t enough – not when championship windows slam shut faster than they open. There’s an uncomfortable truth lingering about this Bills era: for all their regular-season success, something keeps unraveling when the stakes are highest. The plays that work in September stop working in January. The decisions that look smart in October backfire in the playoffs.

Now, a former Bills executive is saying out loud what many fans whisper after playoff losses. There’s a brutal truth about why this team can’t get over the hump. And his comparison for Allen? It cuts deep. The damning critique finally has a name—and it’s direct. Former Bills GM Doug Whaley didn’t mince words on The Zach Gelb Show about why Buffalo keeps falling short, “The thing that I struggle with in Buffalo is when everything’s scripted, that team seems to be okay. But when it comes down to a fourth quarter… they always seem to dribble down their leg.” That’s a serious issue.

Asked if that’s on Sean McDermott, Whaley was blunt: “I think so… every time it came down to crunch situations late in the game where he had to make a decision that was not on his script, something always went wrong.” Well, he isn’t wrong.

The numbers back the frustration. Under McDermott and Allen, the Bills are 5-6 in playoff games since 2019. Three of those losses were one-score games where late decisions backfired:

• 2020 AFC Championship: A Cover-2 breakdown vs. KC with 13 seconds left 
• 2023 Divisional Round: A missed 44-yard FG by Tyler Bass after conservative play-calling 
• 2024 AFC Championship: The controversial QB sneak spot vs. KC 

Whaley’s take cuts deeper because it’s not about talent—Allen’s thrown 21 playoff TDs to just 4 INTs. It’s about when the wheels fall off. And until that changes, the ‘almost’ era might keep repeating itself. But Whaley saved his sharpest take for Allen himself—a comparison so brutally fitting, it might just redefine how we view Buffalo’s star QB.

Josh Allen’s Charles Barkley problem

The hardest truths come in comparisons. When Doug Whaley analyzed the Bills’ championship chances, he didn’t just critique coaching – he reframed Josh Allen‘s entire legacy, “to me, Buffalo will always just hit that proverbial ceiling and they can be the Charles Barkley to the Michael Jordan, unfortunately for Josh Allen, because he’s an incredible talent.” The analogy cuts deep because it fits.

Like Charles Barkley dominating ’90s NBA courts only to run into Michael Jordan‘s Bulls, Allen’s brilliance (21 playoff TDs, 4 INTs per PFR) keeps colliding with Patrick Mahomes‘ playoff magic. Three postseason meetings. Three losses. The latest – last January’s AFC Championship – saw Allen erase an 11-point deficit only to lose on a last-minute drive. 

Whaley sees Baltimore as potentially better positioned: “I think Baltimore still has a chance,” making the Barkley parallel more ominous. Both superstars share haunting similarities: 

• MVP-caliber peaks (Allen 2024, Barkley 1993)
• Clutch performances in defeat (Allen’s 4 TD game vs. KC in 2022, Barkley’s 32/12/10 Finals gem)
• The ‘almost’ legacy (0-3 vs. Mahomes, 0-6 vs. Jordan in title rounds)

At 28, Allen has time. But NFL windows slam shut fast. Jim Kelly‘s Bills reached four straight Super Bowls without winning one. Now Allen battles a tougher truth: being great enough to challenge history, but stuck behind someone rewriting it. As Whaley’s Barkley comparison suggests, Buffalo’s ceiling might not be coaching or talent – just terrible timing. For Bills Mafia, that’s the real heartbreak. Their Jordan wears Chiefs red.