Earlier this week in Bears Bits, I asked what you’d be comfortable with the Bears giving up at the deadline. Ryan Poles answered that one for all of us on Thursday morning.
Chicago sent its 2027 and 2028 first-round picks, plus a 2027 fourth-rounder, to Tennessee for Jeffery Simmons and a 2028 fifth. Since the common draft era began in 1967, no defensive tackle had ever been traded for more than one first-round pick. Simmons is the first.
That’s a steep price by any measure. But I don’t see this as a Super Bowl rental, and I doubt Poles does either. Matt Rooney already laid out what Simmons does for everyone around him on the field. I want to look at what Chicago actually did with its draft capital: it turned two picks that will likely land late in the first round into a proven difference-maker at a key position, for this season and the next two.
This Isn’t the Khalil Mack Trade
Every Bears fan’s mind went to the same place the second the compensation came out. Two firsts for an elite defender? We’ve been here before. Only a handful of defensive players have ever been acquired for at least two first-round picks, and Mack is one of them.
But the similarities mostly stop at the pick count, and the differences are what make this one easier to swallow.
In 2018, the Bears sent two firsts to Oakland and then had to turn around and hand Mack a record-setting extension. They paid twice: once in picks, once in cash. That’s how it went for most of the big names on that short list, too. The acquiring team got the player, then had to pay the player.
December 5, 2019; Chicago, IL, USA; Chicago Bears outside linebacker Khalil Mack (52) rushes against Dallas Cowboys offensive tackle Tyron Smith (77) in the second half at Soldier Field. Mandatory Credit: Quinn Harris-USA TODAY SportsSimmons comes with the hard part already done. Tennessee signed him to a three-year, $105.8 million extension in June, with $100 million guaranteed, and the Titans already cut the $20 million signing bonus check. What follows him to Chicago is under $8 million for the rest of this season and roughly $27 million in cash next year, with the deal running through 2030. His cap hits climb into the low-to-mid $30 million after this year, which is what an All-Pro defensive tackle costs, and the contract reportedly gives the team a way out before the final season.
The other difference is the one that matters most. When the Bears traded for Mack, Mitchell Trubisky was in his second season and still a big question mark. That team was good enough to win 12 games and not good enough to survive a Wild Card game at home. This time, Poles is pushing chips in with Caleb Williams playing some of the best football in the league. The Bears know exactly what they have under center, and that changes the math on everything.
Two Lottery Tickets for a Sure Thing
Start with the picks themselves. If the Bears are the team this trade assumes they are, those firsts land in the 20s, maybe later. Now picture April 2027, with Chicago on the clock somewhere in that range. The dream outcome is a disruptive interior lineman who wins a starting job early and becomes a game-wrecker by year two or three. If the Bears could use that pick on a 29-year-old Jeffery Simmons, it would be a home run, and probably the single biggest move they could make for the defense all offseason. They just made it six months early and got the rest of this season thrown in.
Simmons is what you’d hope one of those tickets turns into, and then some. Since the start of last season, nobody at his position has more sacks (15) or tackles for loss (23). He’s tied for the most pressures among defensive tackles over that stretch, and he leads the group in pressures generated through a double team, turnovers caused by pressure, and third-down sacks. Last year, his pass-rush win rate sat in the 99th percentile. He’s been a tick below that on a 1-6 Titans team this season, which is about what you’d expect when nothing around you is working.
Now drop him next to Grady Jarrett, on a defense that hasn’t had a second interior rusher step up all year. The Bears didn’t spend two firsts on a nice piece. They spent them on the best version of the exact player they were missing, at the biggest gap.
Tennessee Titans defensive tackle Jeffery Simmons (98) reacts to his helmet being torn off against the Green Bay Packers during their game at Nissan Stadium in Nashville, Tenn., Sunday, September 22, 2024. Denny Simmons / The Tennessean / USA TODAY NETWORK via Imagn ImagesSkipping the Guesswork
I understand why people get attached to first-round picks. They’re exciting, and when you hit on one, you get a good player on a cheap deal for years. But you want the pick to land someone who wrecks games at a position that matters. Every so often, a team gets the chance to skip the guesswork and get that player. This was one of those times.
Could the Bears land a player in the late first round who becomes Simmons in a couple of years? Sure, it happens. Could they land one who is what Simmons is today? Probably not, and even the late-round hits usually need a season or two to get there. Simmons is that player right now, and he’ll still be that player in 2027 and 2028, the seasons those picks would have spent growing into the role. Defensive tackle is a premium position, and Chicago now has one of the best in football locked in at a known price.
It helps that the Bears aren’t short on young, cheap talent. Caleb Williams, Rome Odunze, Colston Loveland, and Luther Burden are all still on rookie deals, and they’re far from the only ones. The usual case against trading firsts is that you need those cheap contracts to fill out the roster once the quarterback gets paid. Chicago already has plenty of them. What it didn’t have was a high-value player at an important position on defense.
August 22, 2025; Kansas City, Missouri, USA; Chicago Bears quarterback Caleb Williams (18) warms up during the first half against the Kansas City Chiefs at GEHA Field at Arrowhead Stadium. Mandatory Credit: Jay Biggerstaff-Imagn ImagesThat’s why this move makes sense now and later. Williams is eligible for an extension after this season, and that deal will be huge. When it kicks in, the Bears will still have a young, cost-controlled core around him, plus Simmons at a price that’s already set through 2030. There’s no bidding war, no franchise tag, and no surprises.
The real risk is age. Simmons is 29, under contract through his age-33 season, and had an elbow procedure this past offseason. If he slows down by 2029, the back end of this deal won’t look great. That’s a fair worry, but it’s a year-four worry, and the contract reportedly gives the team an out before the final season. The next two-plus years are what the Bears are really buying, and that’s the stretch where Simmons is most likely to be exactly who he’s been.
In Bits, I said I’d be fine with the Bears pushing their chips in, and that if you didn’t want them spending premium capital to chase a title, you couldn’t be upset in January when the season ended short of one. I still believe that. But this trade is bigger than one January. Poles took two late first-round lottery tickets and turned them into an All-Pro who helps him now and for the next two seasons.
The deadline isn’t until November 10, and there’s still a cornerback conversation to be had. Whatever else happens, it’s hard to imagine a better use for those picks.
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