Favorite Chicago team ever? Caleb Williams and Co. need something more

In this story:
Longtime Bears backer Michael Wilbon of ESPN this week told AM-1000's Tom Waddle and Marc Silverman the 2025 Bears might be his favorite Chicago team of all time.
Millions of Bears fans would agree, especially anyone in their 40s or younger. Time goes by and the number of people who consciously experienced the 1985 Bears stomp all over the NFL as retribution for two decades of their team being a joke is decreasing daily.
The logic Wilbon used is easy to understand and it is the unexpected nature of this Bears rise under Ben Johnson compared to the 1985 Bears or the most dominant of modern team sports dynasties, Michael Jordan's Bulls.
"They were the best teams, you knew they were the best, you just wanted to celebrate them sticking a knife in somebody's heart," Wilbon explained of the 1985 Bears and MJ's teams.
DJ Moore’s game winning touchdown - his second this season against the Packers - same vicinity pic.twitter.com/xSoSP1ZYLH
— StaceyDales (@StaceyDales) January 11, 2026
You could say the same for the 2010-13-15 Blackhawks, for that matter. Those Cups were coming from the day Patrick Kane and Jonathan Toews joined the team. The 2016 Cubs similarly seemed inevitable as the organization gradually strengthened before everyone's eyes.
These Bears are mercurial in their rise like the 2005 White Sox in that regard, but more widely regarded because in this city there are Cubs fans and Sox fans, but everyone is a Bears fan.
Yet, comparing these Bears to past Chicago sports champions is unfair because the storybook team needs the storybook ending to be truly legendary. This story is still being written. Right now, it's merely been a thrill ride.
Wilbon (@RealMikeWilbon) Says he LOVES THIS BEARS TEAM MORE than ANY Chicago Team EVER!!
— ESPN Chicago (@ESPN1000) January 14, 2026
Full Segment: https://t.co/PbMdZ4ubKU@marcasilverman @twaddle87
Brought to you by: @Wendys
Savor the flavor of Wendy’s new chicken tenders. Gotta have Tendy’s? Gotta Be Wendy’s.… pic.twitter.com/p838XzXMFr
Wilbon is talking about personal likes and dislikes more than success, though. He's falling victim here to how time alters perception. It plays tricks with memories.
Time is perspective. It's why Colton Loveland can call LeBron James greater than Michael Jordan.
The poor kid never knew true greatness. Pity him. For others, things have happened to diminish the memory of the greatest Bears team ever, in 1985, as well.
Relive the magic of Michael Jordan's unmatched basketball prowess! Witness the defining moments that led the Bulls to victory and a celebration for the ages. #MichaelJordan #BullsNation pic.twitter.com/FL3KZvapHO
— BillionDolllarMind.Jerath (@Doctorniva) January 17, 2026
The 1985 Bears team actually was that sudden storm surge like this one, it just carried over from the second half of the 1984 season.
The 1985 Bears have become boorish to some over the year because of how they handled success poorly as they failed to win two or three more titles when possible. For this reason, some are quick to adopt the current team.
Trailing the Redskins 3-0 in the second quarter of the 1984 NFC Divisional, #Bears safety Todd Bell HAMMERS Joe Washington — forcing a fumble and changing the entire complexion of the game.#DaBears win, 23-19 — their first postseason victory in 21 years.
— Kevin Gallagher (@KevG163) December 30, 2025
December 30, 1984 pic.twitter.com/QyPwnOWcHJ
The coach's ego, the defensive coordinator's desire to be a head coach, the entire team's ego, and above all else mismanagement by ownership, combined to spoil the 1985 experience. It didn’t ruin it, however. This can't really be held against them because they also inspired as they rose to prominence and delivered in such a way that no one could ever forget it.
At one time, they too were like this team, a young force of hope.
November 3 — the Chicago Bears defeat the Cincinnati Bengals on a 58-yard walk-off TD with 25 seconds left 🥶
— m (@downbadbears) January 1, 2026
Caleb Williams to Colston Loveland in one of the most memorable wins of the season pic.twitter.com/CQGwXxTIut
The William Perry moments when he flattened George Cumby into Gumby for a touchdown and caught a TD pass at Lambeau Field were not thrilling in the same way DJ Moore's back-to-back daggers to end miracle comebacks were, but were so satisfying to Bears fans as they showed total disrespect for their rivals to the north.
Consider that team a Ben Johnson locker room F-bomb except right in the face of former Packers coach Forrest Gregg. The 44-0 road victory over Dallas, when they yelled at exiting Cowboys fans in the third quarter to come back and watch America's Team get embarrassed on their own field, was nothing but pure satisfaction. They thumbed their noses at the entire NFL/network establishment after years of being neglected.
1985 Bears were once in this position
That team was the great underdog turned colossus, and this one is still getting past underdog status. Look at the line for Sunday's game. They're 4 1/2-point dogs to a warm-weather team coming to the Chicago ice box.
Oct 21, 1985: In a "Monday Night Football Game," the Packers lost to the Chicago Bears 23-7. The Bears used 320lb William "The Refrigerator" Perry as a running back. Twice he blocked for Walter Payton and once he carried and scored a touchdown running over Packer LB George Cumby. pic.twitter.com/NHKj41lYsH
— Jack Eich (@jackeichsays) October 21, 2023
What this team has that no Bears team had was the gunslinger. Not even Jim McMahon qualified because he had a hard time keeping his body intact.
Caleb Williams creates hope that anything is possible, and makes for pure excitement. He hasn't taken it to the top yet, though.
Ultimately it's personal choice, but this Bears team needs the ultimate happy ending before it should replace the 1985 team’s place in the heart of any aging fan. Winning it all matters. No one really talks about the 1995 Colts very much because they couldn’t get to the title game. They’re just a blip on the NFL radar because of Capt. Comeback Jim Harbaugh.
For maybe half of fans, though, because of their age there is no doubt this Bears team would naturally be No. 1.
Caleb Williams final two drives against the Giants pic.twitter.com/VuwueSpVmu
— Dave (@davebfr) November 10, 2025
When the next best memory a Bears fan has is Devin Hester dancing to the end zone to start Super Bowl XLI, only to see it end the other way with Kelvin Hayden taking Rex Grossman's pass all the way back for a clinching pick-6, it's easy to call this one your favorite team.
Other than that, the only other similar memory is the way the 2018 defense suddenly started flattening people, and that one ended up laying on the ground in Soldier Field's north end zone after striking the upright and crossbar following a boot by he who must not be named.
This one will be a fond memory for all, even with a letdown ending.
Even the older Bears fans could get on board with this idea expressed by Wilbon if the ending is Williams and Johnson hoisting the Lombardi Trophy.
Ben Johnson to his team in the Bears locker room postgame:
— NFL Memes (@NFLMemes) January 11, 2026
"MAN, F**K THE PACKERS. F**K THEM!
F**KING HATE THOSE GUYS!"
pic.twitter.com/OJ7awQW3AR
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Gene Chamberlain has covered the Chicago Bears full time as a beat writer since 1994 and prior to this on a part-time basis for 10 years. He covered the Bears as a beat writer for Suburban Chicago Newspapers, the Daily Southtown, Copley News Service and has been a contributor for the Daily Herald, the Associated Press, Bear Report, CBS Sports.com and The Sporting News. He also has worked a prep sports writer for Tribune Newspapers and Sun-Times newspapers.