The biggest question of all facing the Bears going into this offseason is not whether they draft a defensive end or tackle, or even a safety.
It's not whether they should try to trade away their future for Maxx Crosby or sign Trey Hendrickson.
Nor is it what they'll do to fortify left tackle after the knee injury threatens to take Ozzy Trapilo out deep into next season, according to GM Ryan Poles.
It's not even how much better Caleb Williams can get in Year 3, although that's probably No. 2.
Caleb Williams was ranked No. 8 by @TheNickShook from @AroundTheNFL for quarterbacks who started a game in 2025 season.
He's behind Sam Darnold, Trevor Lawrence, Justin Herbert, Drake Maye, Dak Prescott, Josh Allen, and Matthew Stafford.@dan_bernstein and @MattAbbatacola… pic.twitter.com/SwEm9UgADH
— 312 Sports Chicago (@312SportsChi) February 13, 2026
It is simply this: Can they do it again, but take it to a Super Bowl this time.
If history teaches us anything, the answer to that one is a disappointing "no."
Percentages say Bears can't make playoffs
The Bears in 2025 did something once considered unique, but less so now. They went from worst to first. No team in this century has gone from worst to first, then come back the next season to win a Super Bowl.
Last time bears won the north they tanked for 6 years. Also you guys had 7 comeback wins. That’s probably not going to happen again. https://t.co/MnvDFsxnOP
— Taylor (@PNWPANCHO) February 13, 2026
We'll cut it off at the turn of the century because teams did worst-to-first turnaround at a much lower rate before 2000. Back when the NFL had fewer teams and teams didn't have free agency or later didn't quite know how to use it well, this was tougher to achieve. From the start of the Super Bowl era in 1966 through 1999, only 18 teams did this in 34 seasons.
Since 2000, 30 teams have done it in 26 seasons and the two this year who did it—the Bears and Patriots—obviously haven't played their next season. So, there are 28 teams in 26 seasons who went from worst to first and only seven of the 28 made it to the playoffs the next year after they performed this dazzling feat.
Caleb Williams is a walking highlight🥶
pic.twitter.com/S2AmnfYLCg
— SleeperBears (@SleeperBears) February 13, 2026
And Super Bowls?
The only team to even get to a Super Bowl the year after they had gone from worst to first was a team long-time Bears fans will remember well. It was Brian Urlacher, Peanut Tillman, Lance Briggs and the 2006 Bears. Of course, they lost when Rex Grossman was trying to move them for winning points in the fourth quarter and Kelvin Hayden returned it for a touchdown.
Please enjoy this Packers reaction video compilation on this glorious Sunday! pic.twitter.com/yYl17Hefg6
— Sarah🐻⬇️ (@thechicagosares) January 11, 2026
None of the other 27 worst-to-first teams made the Super Bowl the following season and most of them failed miserably.
The consensus seems to be they dropped back into third place the following season. Ten of the 28 did that. Seven dropped all the way to last place, where they had been two years prior. Four finished second but didn't make it as wild cards. The last place schedule, followed by a first-place schedule, is often too much to overcome.
Then there is the problem of following up with more talent from later in the draft, or without much salary cap cash.
2026 is the Bears year 🔥 pic.twitter.com/kfUNuHBE9z
— BetMGM 🦁 (@BetMGM) February 12, 2026
"I think that's part of the thing, one, can you self-evaluate and be critical of yourself and your team to make sure that you know what you have in the building," Poles said. "And then can you keep pounding away and stick into your process?
"You make tweaks of course, but stick to the process of bringing in the right types of people and it usually works out for you."
The odds say the Bears have only a 25% chance to make the right changes to get to the playoffs when 21 out of 28 missed the playoffs the next year after a worst-to-first journey.
#Bearmanos Lo mejor de nuestros Chicago Bears es que en cada partido demostraron progreso
Qué bien se siente ver el crecimiento de nuestro QB Caleb Williams junto con nuestro HC Ben Johnson
El 2026 ilusiona ¡🐻⬇️#DaBears #NFL pic.twitter.com/cV94jJ7kSI
— Bearmanos (@Bearmanos) February 13, 2026
Making it to a Super Bowl for much of 2025 for the Bears seemed almost unthinkable, just like it had in 2018 after they struggled so long to become a playoff team. But it's been easier for teams in this century to finish last and go straight to the Super Bowl the next year than it has to reach the Super Bowl the year after they went from worst to first.
Six teams since 2000 have done what the Patriots did and went straight to a Super Bowl after being in last place.
Opportunity lost for the Bears?
DJ Moore will be traded this off-season - and I wouldn’t have thought that one year ago. But looking at the team, the cap situation, and the player, at this point - a trade is the best move for the Chicago Bears.
Here’s why: 🧵👇
— Ben Devine (@Chicago_NFL) February 13, 2026
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X: BearsOnSI