How the 2026 Bears can avoid past disappointments

The Chicago Bears just enjoyed a celebratory offseason for a team that didn’t win the Super Bowl or even reach the conference title game.

Heck, the 2025 Bears actually lost three of their final four games and it didn’t matter.

Caleb Williams still made the cover of Madden and ate chicken wings on YouTube with Sean Evans.

Colston Loveland attended the Taylor Swift-Travis Kelce wedding and Luther Burden III became one of the most talked-about breakout candidates for league-wide stardom.

Ben Johnson also made headlines for saying he wants to have the highest scoring offense in league history and ESPN named the Bears the most watchable team in the league.

The good vibes speak to what being a member of a winning Bears team means … and also just how rare it’s been the last three-plus decades.

Before last season, the Bears had won just five division titles in the previous 35 seasons.

And only one of the ensuing squads — the 2006 Super Bowl team — successfully defended the previous year’s title and went farther in the playoffs.

The other four all experienced a disappointing dropoff, missing the playoffs and returning the franchise to a state of mediocrity from the excitement they’d created the year before.

This current Bears team feels different, of course. The Williams-Johnson partnership plus the arrival of other young offensive stars seems to have opened an era for Bears fans that has actual staying power.

But while that hopefully may prove true for the long run, there are no guarantees in the short run.

So as the 2026 Bears look to continue wrapping the city around its fingers, I thought I’d take a look at the previous five division winners.

What went wrong with the four that didn’t deliver?

And how did the 2006 team follow through to keep the party going?

Let’s take a look at each team, starting with the disappointments, to see if we can identify the common pitfalls the 2026 team will need to dodge …