Will Josh Allen Break Through? How He’s Trending To Be The Mickelson To Mahomes’ Tiger

Josh Allen is hopeful that he and the Buffalo Bills will finally get over the hump and win a Super Bowl one of these days. However, with each passing season, FOX Sports’ Colin Cowherd believes that Allen is inching closer to becoming the guy who played second fiddle to an all-time great. 

In a recent interview with ESPN, Allen iterated that “You knock enough at the door, it’s going to open at some point, and that’s what we have to keep doing.” But Cowherd is skeptical about that belief. 

“Phil Mickelson’s prime was Tiger Woods’ prime. Well, Josh Allen and Patrick Mahomes entered the league one year apart. Mahomes got the better owner, arguably, GM, coach and weapon, Travis Kelce,” Colin Cowherd said on Wednesday’s edition of “The Herd.” “In an offensive league, the weapon matters. Offensive coach in Andy Reid, so a lot of advantages just didn’t go Josh Allen’s way. … I tend to think the Los Angeles Rams are going to win the NFC, the better conference, and I like Buffalo in the AFC.

“I think the DJ Moore pickup and the offensive coach [promotion of Joe Brady] all works [for the Bills], but Josh Allen, this is the inevitable question: ‘Bro, when are you going to win one [a Super Bowl]?’”

Allen had another standout season in 2025. The four-time Pro Bowler and the 2024 NFL MVP totaled 3,668 passing yards, 25 passing touchdowns, 10 interceptions and a 102.2 passer rating, while completing 69.3% of his passes. He also rushed for 579 yards and 14 touchdowns.

But after Buffalo defeated the Jacksonville Jaguars in the AFC wild-card round, Allen threw two interceptions and lost two fumbles in an overtime loss to the Denver Broncos in the AFC divisional round. Through the first eight seasons of Allen’s NFL career (2018-25), the Bills haven’t advanced past the AFC Championship Game, which includes going 0-4 against Patrick Mahomes and the Kansas City Chiefs in the postseason; the Chiefs have won three Super Bowls with Mahomes under center (2019, 2022 and 2023 seasons).

On that note, the Bills’ five-year run of winning the AFC East (2020-24) ended last season (2025) with the New England Patriots winning the division at 14-3 in their first year with Mike Vrabel as head coach, while then-second-year quarterback Drake Maye was the runner-up for the NFL MVP Award and the team reached Super Bowl LX.

“Are you going to be playing road playoff games? Ask Tom Brady about playing road playoff games at Denver: It never worked out well. A lot of those San Francisco 49ers playoff highlights with Joe Montana, they were at home. A lot of Brady’s highlights, they were at home, so that’s what worries me,” Cowherd said about the Bills. “Not that the window’s closed. Rather, New England now has the better coach, an elite quarterback, a great owner [Robert Kraft], lots of historic momentum and success. That and a lot more good, young players.

“You can blame the GM, but some of it becomes the Patriots have Drake Maye on a rookie deal and the Bills are paying Josh Allen a lot, and you got to move off really good players.”

The 30-year-old Allen is entering the second season of a six-year, $330 million contract, with the $55 million average annual value tied for third among NFL quarterbacks.

The Bills split the 2025 regular-season series with the Patriots, who loaded up their wide receiver room this offseason, acquiring three-time Pro Bowler A.J. Brown from the Philadelphia Eagles and signing former Green Bay Packers receiver Romeo Doubs (four-year, $68 million deal), among other moves. Granted, New England released 2025 leading receiver Stefon Diggs.

While they won AFL Championships in 1964 and 1965, the Bills are one of 12 NFL franchises that haven’t won a Super Bowl. And, of course, Buffalo lost four consecutive Super Bowls from 1990-93, and it hasn’t made it back there since.