A long-expected move from the Chicago Bears was finally announced on Thursday afternoon, with NFL insiders Ian Rappoport and Adam Schefter breaking the news that the Bears and general manager Ryan Poles had agreed to a contract extension that ties Poles to Chicago through 2029. Incidentally, this puts him on the exact same timeline as new head coach Ben Johnson.
Poles received this extension despite his team winning just 15 games in three years. This means that either the Chicago Bears organization is betting on the upside of this new roster and coaching staff, or that they are comfortable assigning 100% of the blame for the past three seasons to former head coach Matt Eberflus.
Either way, with this new contract in hand, the expectations for Poles' team increase drastically. Here are four milestones that the Bears need to hit soon to make this contract extension for Poles work.
1. Finish a season with a winning record in 2025
Thus far, the Bears' best season under Ryan Poles was 2023 when they went 7-10. It was understandable at the time, as the Bears were coming off a total teardown season, but losing more than they win will no longer be accepted. Given the upgrades to both the roster and the coaching staff, winning 9 games should not be an outlandish goal.
Poles has now drafted his quarterback, assembled his own team, and hired two head coaches. Starting in 2025, responsibility lies squarely on his shoulders.
2. Win the division within three years
Poles infamously declared in his introductory press conference with Chicago that the Bears were going to 'take the NFC North and never give it back'. They've finished in dead last by a wide margin in each of the three seasons since then. That cannot continue.
I'll give Poles and the Bears three years to accomplish this objective, but only because the NFC North is a brutal division right now. They ought to improve to at least third place in 2025, and then compete for the division crown in 2026 and 2027.
3. Win a playoff game by 2026
The Bears are tied with the New York Jets for the longest active streak without a playoff win at 14 years, ahead of just the Las Vegas Raiders and Miami Dolphins. This streak needs to end earlier than their division championship drought because they can at least make the playoffs, even if they don't win the division.
It doesn't have to be this year; that would be asking a lot. But if all goes according to plan, the Bears ought to be serious contenders by next year, and a Wild Card win should be well within reach.
4. Win a Super Bowl
Is asking for a Super Bowl title by 2029 a bit unreasonable? Perhaps, but look at it this way. The two most important pieces of a championship team are the quarterback and the head coach. If Caleb Williams and Ben Johnson both live up to the hype around them when they joined the team, then the Bears will likely be no worse than Top 5 in the NFL at both quarterback and head coach. That's a recipe for success right there.
Yes, this is asking a lot of Ryan Poles to deliver a championship, but no one deserves a Super Bowl title more than the Chicago Bears and their passionate fanbase. If all goes according to plan, by this time next year, I won't be the only one expecting the Bears to throw open their Super Bowl window for the rest of the 2020s.
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