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Windy City Gridiron picks Bears-49ers

The Bears have a winnable game. The Bears have a must-win game. Welcome to October.

San Francisco 49ers versus Chicago Bears Photo by Nhat V. Meyer/Digital First Media/The Mercury News via Getty Images

The Chicago Bears sitting in desperate straits right around Halloween should be something we’re all accustomed to by now. None of this is new. It’s who the Bears are: a .500 team with a “winnable” game, whatever that could possibly mean when you struggle to score 20 points, in danger of having their entire season slipping away before all the leaves turn orange and crunchy. None of this frustrating mediocrity, this utter inability to elevate play against stiffer competition, is unfamiliar in the least.

The 49ers are a squad in a similar position to the Bears. They, too, drafted a quarterback in May 2021, Trey Lance, that will probably need a little more seasoning before he’s ready to reach any star potential. While balancing the future of their franchise, they, too, have a roster largely built to win in the here and now, but one that unfortunately peaked a couple of seasons ago. They’re so similar to the current iteration of the Bears, in fact, that Kyle Shanahan has won the same number of games (31) since he became the 49ers’ head coach in 2017, that Matt Nagy has won with the Bears (31) since taking over in Chicago in 2018. As much as it might think it deserves better, misery can’t escape poor company.

Neither of these teams has a discernible identity. They have a sprinkling of stars and franchise players here and there, quarterbacks that might burn the league to the ground with their arms and legs soon enough, but nothing that says “progress” or “this is the way.” I suppose that describes more than half of the professional sport. Welcome to the NFL.

These Bears are probably better than these 49ers. And they could use a win much more. I shudder to think what happens in Halas Hall, what further controversy ensues if they don’t get it. If you haven’t hit rock bottom yet — believe me, even by their standards, the Bears have not seen the rotten depths of their dark abyss — then it can always get worse. Always.

Windy City picks Bears-49ers and every other NFL game in Week 8. You can check out all of this week’s odds from our partner, DraftKings Sportsbook.