The Chicago Bears, under head coach Ben Johnson and with quarterback Caleb Williams on a rookie contract, believe they are right in the middle of a legit Super Bowl window. Last season’s trip to the NFC Divisional Round opened that door and the team’s 5-2 start to the 2026 season confirmed this team is legit.

However, in a competitive NFC, you have to be the aggressors if you want to win. The Green Bay Packers knew that after swinging two first-round picks for Micah Parsons. The Los Angeles Rams knew that after making a deal for Myles Garrett. Earlier this week, we saw the Seattle Seahawks add Quenton Nelson and the San Francisco 49ers add DeForest Buckner.

It’s a nuclear arms race in this conference and if you’re not developing your weapon, you need to by one. And the Chicago Bears just bought the biggest warhead on the market.

Jeffery Simmons was a necessary swing for the Chicago Bears to keep Super Bowl hopes alive

The Bears had a talented roster and a strong coaching staff. That alone bodes well for this team having a successful postseason run again. But, it wasn’t going to be enough for this team to contend for a Super Bowl. Everyone saw it, including general manager Ryan Poles.

And so, the Bears pushed all of the chips in on Thursday, trading two first-round picks and a fourth-round pick to the Tennessee Titans in exchange for defensive tackle Jeffery Simmons and a future fifth-round pick. A massive, and costly, swing for the Bears to do, but it was a necessary swing if this team wants to really compete for a Super Bowl.

This team needed a dominating threat on defense. Ian Rapoport said the Bears made a push for Buckner prior to landing in San Fran. After missing the swing, the Bears had no choice but to aim for the fences. And they made contact.

The Bears now have that difference-maker up-front in Simmons, who is easily the best defensive tackle in the game right now. You pair that with Montez Sweat off the edge and the Bears have two players who could take over a game. Oh yeah, while having one of the top offenses in the league on the other side of the ball.

Expensive? Yes. Risky? Definitely. Necessary? Absolutely. The Bears now have that final piece to make a run at a Super Bowl, not just in 2026 but for the next two years. This is now a clear two-year window for the Bears given how the roster is constructed, along with Simmons’ deal, and Williams’ upcoming extension.

Why this feels different than 2018

Simmons becomes the latest defensive player to be traded in a blockbuster deal that included multiple first-round picks. Some of the recent others include Micah Parsons, Sauce Gardner, Jalen Ramsey, and Khalil Mack.

The latter is worth noting. In 2018, the Bears had a talented roster led by a young quarterback and a hot-shot offensive head coach. Ryan Pace made an all-in swing on that roster to acquire Mack from the Raiders. Things start off hot with the Bears winning the NFC North that season, but the Bears went 34-31 from 2018-2021 without a single playoff win.

It was a clear reminder that if you go all-in, you better be absolutely confident about the other pieces in place. Mitch Trubisky had his questions and Matt Nagy quickly flamed out after his 2018 Coach of the Year season. And now, the Bears are in the same position once again, but the vibes are totally different in Chicago.

Caleb Williams and Ben Johnson are not Mitch Trubisky and Matt Nagy. The duo proved that last season and have continued to get even better in Year 2. The Bears felt that energy and it was a different feeling compared to what the franchise felt in 2018. This feels real and now the results could look a lot scarier for the rest of the NFL.