The 2026 NFL trade deadline is less than two weeks away, and a handful of major moves. The latest involves star defensive tackle Jeffery Simmons.

As NFL insider Tom Pelissero first reported, the Titans are sending Simmons and a 2028 fifth-round pick to the Bears in exchange for ’27 and ’28 first-round picks and a ’27 fourth-rounder. As we’ll get to below, Simmons signed a three-year, $106 million record-setting contract extension with Tennessee this summer that kicks in next season and runs through 2029. 

Let’s get to grading the trade of Simmons from the Titans to the Bears.

Bears push all their chips to the center in quest for Super Bowl title

After taking care of business last Thursday night against the Patriots, the Bears are now 5–2 to start the season and with quarterback Caleb Williams playing at an all-world level, have reason to believe that they can compete for a Super Bowl title this coming February. Chicago’s offense is third in the NFL in yards per game (390.7), eighth in points per game (25.7), and, with Williams, has scored 30-plus in each of the past two weeks.

The Bears’ defense, meanwhile, has been solid, forcing 10 turnovers, sacking opposing quarterbacks 19 times and holding opponents to less than 15 points three times. Still, after trading Gervon Dexter Sr., who was heading into the final year of his rookie contract, to the Falcons this summer, the Bears have started the season with a void to fill up front. That’s where Simmons comes in.

A 2025 first-team All-Pro, a two-time second-team All-Pro and a four-time Pro Bowler, Simmons has logged 414 total tackles, 46.5 sacks, 72 tackles for loss and nine forced fumbles throughout his career, and in ’26 leads all qualified defensive linemen in tackles (38) and is second in stops (28) while registering 28 pressures and four sacks with a pressure rate of 12.0%. The 29-year-old has still got it.

Is it a gamble for the Bears to ship away their next two first-round picks? Certainly, just look at what’s happened to the Colts after they did the same for cornerback Sauce Gardner at the 2025 deadline. That said, Chicago is in far better shape from top to bottom than Indianapolis was at this time last year, and with Simmons under contract through the ’29 season, the Bears have multiple years to make this move pay off.

Grade: B+

Titans remain in a rebuild amid Robert Saleh’s first season at helm

Speaking of the contract, the massive three-year, $105 million deal that Simmons signed this offseason made him the highest-paid defensive tackle in football at the time. After the Titans’ measly 1–6 start to the 2026 season, however, it’s clear that they’re far from a team that can win consistently in the foreseeable future.

That’s why, while it likely hurt, it made plenty of sense for Tennessee to trade not only a team captain, but a homegrown talent that was arguably its best player. 

With the return they received from the Bears, the Titans now own two first-round picks in each of the next two drafts, giving general manager Mike Borgonzi and the rest of Tennessee’s front office some extra draft capital to construct a competitive roster for coach Robert Saleh. Beginning with a 2027 draft widely considered to be among the most talented classes in years, it also gives the Titans the option to either build around quarterback Cam Ward, or pivot off the 2025 No. 1 pick and find another option.

Either way, this was the right move for a Tennessee team that’s working toward 2027 and beyond.

Grade: A