It is coming up on 40 years since the Chicago Bears last won a Super Bowl.

The ’85 Bears went 15-1 in the regular season and steamrolled their way to the Lombardi Trophy.

Kay Adams asked former Bears linebacker Mike Singletary — a key part of that dominant Super Bowl defense — if he can believe the franchise hasn’t won another since.

“No,” Singletary said on the Up & Adams Show with Kay Adams. “I mean, obviously at that time, with the talent that we had, the coaching staff, the whole nine yards, there’s no way that I would have even entertained anything like that.”

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Forty years later, the Bears are led by a second-year quarterback, Caleb Williams, and rookie head coach, Ben Johnson.

As training camp approaches, Williams reported when Bears rookies did, which is earlier than he had to. Singletary believes that is the sign of leadership the Bears need.

“It’s a great message,” Singletary told Adams. “It sends the message that, ‘Hey, I’m willing to do everything that I have to do, in order to get the wins that we need, to get into the playoffs, to get to the Super Bowl.”

“It sends a message that, ‘Hey, I’m willing to do everything I have to do in order to get the wins we need.’”

NFL Hall of Famer Mike Singletary talks about Caleb Williams on @UpAndAdamsShow! pic.twitter.com/KGjQq8kFc3

— Marquee Sports Network (@WatchMarquee) July 21, 2025

The Bears haven’t won a playoff game since the 2010 season, and have only made the postseason twice during that timeframe.

The 2024 Bears finished last in the NFC North with a record of 5-12 despite winning their last game at Lambeau Field. If there’s one league a team can go from worst-to-first in the span of a season, it’s the NFL.

There have been 25 instances of teams finishing in last place one season, and then winning their division the next since 2002, per ESPN.

A playoff appearance, let alone a division title, would send Chicago into a frenzy.

Are the 2025 Chicago Bears a playoff team?

“Could be,” Singletary added. “I think from what I saw last year, it definitely could be.”

The Bears are currently +194 to make the playoffs this season, with their win total set at 8.5 wins, per FanDuel Sportsbook.