Buccaneers, Bears: Week 9 Game Preview

Anyone watch Monday Night Football? Wow, the Bears look good. Ben Johnson, Caleb Williams, and their Chicago Bears seem like they are on a collision course for a deep playoff run in 2026. So yes, the Bears are hot— Steaming, but so are the Buccaneers. Tampa Bay is coming off two-straight wins, three of their last four and has seemingly found their new formula for offensive success. Will those good vibes and momentum carry over into the Chicago night on Sunday Night Football?

How can the Buccaneers win?

Be the line they claim to be.

The Chicago Bears are no joke and the Tampa Bay Buccaneers will need to be all the way buttoned up to be able to stay with Chicago in this game. The Bears have a lot of things going for them in 2026, but their most recent addition may be the scariest. Chicago’s highly publicized trade for Jeffery Simmons opened some eyes when they made it. For those who haven’t seen may Titans’ games over the years, Monday night may have opened some more— Simmons is in the elite class of football players in the NFL and after spending years on a losing team, he looks motivated and rejuvenated. The trade for Simmons was an all-in move, the kind of move teams make when they have one goal on their mind— The Bears are a Super Bowl or bust team.

The trade paid immediate dividends, Simmons’ first game with Chicago was a watch what I can do performance as he snared a team-leading six tackles (two for a loss) and a sack. For the Buccaneers, this game will be the game where their offensive line needs to prove the last two weeks true.

Tampa’s season began horrifically, 0-4, a quarterback injury, and more importantly for the sake of this discussion, an offensive line that was woeful. Tampa Bay’s offensive line came into the season projected to be one of the strongest units on the team, perhaps in the league, depending on who you asked. Through the first four games, the Buccaneers allowed 20 sacks. Baker Mayfield spent most of those first four games running in circles behind the line of scrimmage like Fran Tarkenton, until he ran himself into an injury. In the four since, Tampa’s only surrendered seven sacks with five of the seven coming against the Pittsburgh Steelers.

Tampa Bay will be and should be the underdog on Sunday. If there is any chance that an upset is in the cards they will need to protect their quarterback. Baker Mayfield is going to have to attempt more than three passes in this game to lead the team to victory and he will need to be upright to do so. Chicago has an absolute game-wrecker on their defense, he will make his plays— The Bucs can’t expect to wipe Jeffery Simmons out of the game, however, they cannot allow the game to devolve into what fans saw earlier in the season from this offensive line, Baker Mayfield, and the passing game.

How can the Buccaneers lose?

Lose contain of Caleb Williams.

Caleb Williams might not be a truly great quarterback, though he does seem to be enroute to that status in short order, but he is a truly special athlete. No, he isn’t running 4.2 40’s or leaping 13’ in a broad jump but he is as all around dynamic as they come. One of the issues Tampa Bay might have is Williams simply does not throw interceptions. Caleb has missed some time this year, but he has only thrown one interception— Last year, just seven. Williams’ lack of interceptions isn’t even a Ben Johnson related statistic because dating back two years ago, pre their union, Williams tossed just six while throwing 20 touchdowns for a better than 3:1 touchdown to interception ratio. In his career (three years), Williams has thrown less interceptions than Baker Mayfield did in 2024—Turnovers may be off the table.

Another key issue that Caleb Williams presents is his elite management of the pocket. Williams is not a runner, but he is quite mobile. He has a phenomenal ability to majestically glide up, back, or out of the pocket towards free space and away from danger. Todd Bowles and the Buccaneers’ defense will need to work tirelessly to mitigate that on Sunday night. Williams will dagger the Bucs with big plays off script if they let him.

Bowles and the Bucs have been somewhat of mixed bag against mobile quarterbacks, different matchups bringing about different results, but Caleb Williams will represent a very unique challenge. Williams is not just looking to move around the pocket to buy time to throw— He isn’t just looking break out of the pocket so that he heave the ball down field on a broken play— He won’t be looking to run outside of contain so that he can scramble for yards to move the chains— Caleb Williams will be looking to do any and all of the above. He is special and he has proven that he can do each and every one of those things on any given play— Meaning, the Buccaneers must be dialed into the details on their rushes, sound in their tackling, and if they are caught lacking and take even just one snap off Williams could gash them for a game changing play.

Todd Bowles’ defense has been reliably solid in 2026, as of late they’ve been exemplary. Sunday night’s game against Chicago will be a true test. Caleb Williams has the ability to put a defense on a poster, he and Ben Johnson have left a decent amount of carnation in their wake. Can Tampa Bay contain Caleb Williams and stay off his highlight reel?