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Bears’ 2021 offseason roundtable: Whatever it takes

The Bears’ leaders have a stark choice. Push in whatever chips they have left to try and win soon, or cut their losses and gamble again, when ready, in the future. Whatever path they take likely defines the organization for the next decade.

Tennessee Titans v Chicago Bears Photo by Nuccio DiNuzzo/Getty Images

When the Bears traded up to draft Mitchell Trubisky in 2017, that was merely the first domino. When they signed Allen Robinson and traded for Khalil Mack in the ensuing off-season, their intentions were clear — the goal was to win a Super Bowl, and soon. Three years later, following the end of two disheartening Wild Card defeats and two straight disappointing .500 finishes, it’s certain they have gained no meaningful ground in achieving that stated goal. They are no further along in the journey to hoist a silver trophy above their heads than they were before they put their heads on the line for Trubisky and Mack.

In the words of one eternally wise, muscle-bound freak, “Unjustifiably a position I would rather not be in.”

Win-now in 2018 was doubled down upon in 2019, when apparently all the Bears needed was a kicker to reach their Lombardi Trophy dreams. Remember that adorable reality? Simpler times. After it was abundantly clear the Bears needed more than a kicker who could reliably make more than 85 percent of his field goals at 2019’s end, rather than take a step back for a year, Chicago doubled down on high-priced free agents (Robert Quinn and Jimmy Graham, say hello!) with minimal juice left. The result was predictable: No Man’s Land, with myriad needs everywhere and no prayer to escape such a nightmare barring a steadier hand.

The prospect of a steadier hand seems like wishful thinking considering that despite two playoff appearances in six years, a man with one of the itchiest asset trigger fingers, Ryan Pace, remains at the helm. His options on the table are largely the same as they were last spring. He can either continue to double down and sacrifice future resources to try and win with a team that, from the outside looking in, could theoretically contend with a few major tweaks here and there. Or he could demonstrate a measure of patience, recognize that the title window temporarily opened in 2018 is now closed, and rebuild the Bears’ bedrock (offensive line, for example) to win wholly again after 2021.

Option 1, in the event it works out, means the Bears are playing in a neutral warm weather site in February in the near future. Perhaps they’re even winning! Option 1, if it blows up in Pace’s face, means they continue to fizzle out in mediocrity. It turns into a situation where a top-heavy Bears team has little means to pick themselves up off the mat with a legitimate rebuild in the coming years.

Option 2, in the event it works out as planned, has the Bears hover around or a tad below .500 over the next season or two while competing. They strengthen their foundations on offense, perhaps gain another bona fide field-tilter or three, and are prepared to contend over a fleshed out extended window, rather than squeeze in a window over a couple of years. Option 2, in the event it blows up in Pace’s face, means he has little to show for postseason success on his resume as the Bears aren’t trying to compete in January for the foreseeable future. It might also mean he potentially loses his job, but that was somewhat in doubt anyway.

Whatever path the Bears’ head honcho does end up turning onto will assuredly be the most important step toward how this franchise is remembered in the 2020s. If the NFL stands for “Not For Long,” we’ll have appropriate clarity on this situation soon enough.

In the final part of our 2021 off-season primer roundtable, the staff addresses the elephant in the room: Whether the Bears should still be trying to contend, or whether they should be reloading and playing a familiar waiting game.

In case you missed it:

Part 1 on coaching, schemes, and game-plans

Part 2 on organizational and ownership philosophy

Part 3 on free agency acquisitions

Part 4 on salary shedding, player cuts, and trades

Part 5 on draft plans, or lack thereof


Should the Bears still be in win-now mode, or is it time for a retool or rebuild?

Erik Duerrwaechter: No matter how we slice it, the Bears are in win-now mode. Ryan Pace and Matt Nagy truly believe the quarterback position is the final piece to their Super Bowl puzzle. I, myself, am not a believer in “tanking.” There’s no such thing. It’s a loser’s mentality, and the same thoughts are shared by experienced general managers around the league.

Ken Mitchell: I think it’s important the Bears spend all available resources on young players. That means draft, sign, and develop other young players. Old, expensive players? No. Whether that means win in 2021 or not, it’s time to get much younger.

Josh Sunderbruch: This team needs to rebuild, retool, renovate. This team needs its own show on HGTV. The reasons are obvious—it has had one winning season under its current GM, and it hasn’t had a playoff win in over a decade.

Lester Wiltfong Jr.: I would assume they’re going to go all-in again and 2021 is a must-win season. But with the way the McCaskey’s run things, who knows? If they get the right quarterback and tweak the offensive line, they could find themselves back in the playoff mix. If they go with a rookie at quarterback, the franchise may allow them another few years to see if it works. Being stuck in Quarterback Hell is the best!

Will Robinson: A bit of both. Ryan Pace and Matt Nagy will want to win now as much as they can, but there’s only so much you can do right now. A good chunk of their moves will by necessity need to be with an eye towards the future. I can see a path personnel-wise, where they can “reload” for 2021, try and be competitive, while building for the near future. If they can find a way to bring in a solid-good quarterback, it makes things so much easier, especially if they have another draft like 2020. There’s talent on this roster, but it needs a couple of key pieces brought in to tie it all together, and a coaching staff capable of proper schemes to make it competitive.

I can see a path to all of that happening. But I’m not betting on it.

Robert Schmitz: I think the plan for next fall has to be more of a hopeful retool than a win-now bid. The Bears’ offense has too many dysfunctionalities that will take at least a year to fully mesh (Kansas City, Buffalo, Cleveland, and Green Bay weren’t built in a day). If I was Pace and Nagy, I’d be trying to impress George McCaskey with a high-flying offense, rather than wins and losses. As we learned this season, beating Jacksonville doesn’t mean anything if you can’t compete with Green Bay.

Ultimately only Pace and Nagy know what their measurement criteria is. If McCaskey has told them to maximize their wins in 2021, we’ll see a win-now team put together. That team likely won’t perform much differently than the 2020 season and the house will be cleaned afterwards. If this happens, Bears fans are in for a long ride.

Bill Zimmerman: The Bears should be trying to retool this roster. Ryan Pace did an excellent job opening up a three-year Super Bowl window in 2018, the caveat being that Mitch Trubisky become an elite quarterback. Pace missed and the window slammed shut. He’s been trying to pry it back open any which way he can, but the reality of the situation is, he is fighting against the grain to keep the team mediocre. They should be focusing on the young talent on the roster, moving the veterans, building up capital and opening up cap space in 2022 and 2023. That way the Bears are a quarterback, a few draft picks and a free agent spree away from being back in contention. It isn’t as hard as it sounds (if they find the quarterback).

The reality of the situation is that it doesn’t matter how many years Pace and Nagy have left on their contracts. They are both, in essence, on one-year deals. If they don’t improve this year, they’re out. Dthat mean they’ll draft a developmental passer like Trey Lance and retool the roster? Of course not. They’ll be pushing money down the road, drafting players they think can make impacts in 2021, and making things a lot more difficult to construct winning rosters in future years. When the owner gives them an ultimatum on a roster with holes and no quarterback, you open the door to create quite a mess. Maybe they’ll go land Deshaun Watson and prove me wrong. But I expect the Bears to put too much into the 2021 season, remain in neutral or go backwards, have a new general manager and head coach in 2022 with a roster that isn’t ready to win, and a cap that doesn’t give the new regime much of any flexibility.

Jack Salo: I think the Bears are going to try to be cheap, if that answers the question. They have the pieces already on the defense to contend next regular season, most of whom have too much guaranteed money to truly blow up the team. Without a quarterback, they have a low ceiling and maybe 10 wins in a best-case scenario. I think they try again to get their quarterback, knowing full well that solving the most important position in professional sports is the only chance that they can contend in January. It will certainly look like a rebuild if they miss.

Windy City Gridiron Podcast Channel which includes Bear With Me from Robert Schmitz, Bears Over Beers featuring Jeff Berckes & EJ Snyder, Bears Banter hosted by Bill Zimmerman, and T Formation Conversation from Lester A. Wiltfong Jr.; EJ also co-hosts The Bootleg Football Podcast with Brett Kollmann; R. Schmitz has a film breakdown show on YouTube titled Run Pass Opinion; and Steven’s Streaming Twitch Channel from Steven Schweickert.

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