Bears Trade Pitch Urges Chicago to Pull Off Khalil Mack 2.0-Type Blockbuster

Should the Chicago Bears break away from the way general manager Ryan Poles has recently done things and take a huge swing for one of the league’s best pass rushers?

Some think it might be worth a shot considering quarterback Caleb Williams is still on his rookie contract.

In Windy City Gridiron’s July 2 open thread, WCG’s Mongo Peanut floated the following trade idea: the Bears would send 2026 first-round, second-round, and sixth-round picks to the Pittsburgh Steelers in exchange for superstar pass rusher T.J. Watt.

Heading into training camp, Watt has made it clear he’d like a contract extension, sparking trade rumors. Bears fans are all-too familiar with mega-trades for marquee pass rushers. Back in 2018, Chicago sent two first-rounders, a third-rounder and a sixth-rounder to the Las Vegas Raiders in exchange for Khalil Mack.

Might they take a similar swing for Watt?

Dissecting WCG’s T.J. Watt to the Chicago Bears Trade Idea Further

According to top NFL insider Adam Schefter, the Steelers have been getting calls about Watt, and that likely won’t change until a new deal is struck.

“In recent weeks, multiple teams have been discussing whether they can trade for Steelers’ standout T.J. Watt, who skipped the team’s most recent minicamp,” Schefter wrote on X on June 30. “Pittsburgh hasn’t shown any willingness to deal Watt so far, but he’s unhappy with his contractual situation and sources believe outside team interest is likely to increase.”

The Bears signed Dayo Odeyingbo to a three-year deal worth $48 million this offseason, but he’s nowhere near the player Watt is.

“I personally think he’s worth that price,” MP added. “While many look at the Mack trade in retrospect as not being worth it, I see it as the best chance we had to win a championship in nearly 15 years. The 2018 Bears lacked the coaching, QB play, and overall offensive roster building that this current team does – so the addition of an elite pass-rusher opposite Montez Sweat could really catapult the Bears into contention.”

“Maximizing the window where your quarterback is young and cheap, but also has some NFL experience is narrow,” he added. “I think Caleb Williams has all of the ingredients to put it together in Year 2, and T.J. Watt wreaking havoc on defense could be enough for the Bears to contend for a Super Bowl.”

Nothing Matters Unless the Steelers Are Willing to Part With Watt

The Steelers selected Watt 30th overall in 2017 following a standout collegiate career at Wisconsin. Over his first five seasons, Watt consistently posted elite production, topping 10 sacks in four of those years. His relentless style and presence in the backfield have made him one of the premier edge rushers in the league.

The 2021 season stands out as Watt’s hallmark campaign: He registered 22.5 sacks, tying the single-season franchise record set by Michael Strahan, and led the league in quarterback hits and tackles for loss. He earned Defensive Player of the Year honors, along with a first-team All-Pro nod and a lucrative four-year, $112 million extension after that season. He continued this dominance in 2023, leading the NFL in sacks for the third time.

Through the 2024 season, Watt’s excellence hadn’t waned. He recorded his 100th career sack in just 109 games—making him the second-fastest in NFL history to reach that milestone after Reggie White. In 2024 alone, he tallied 11.5 sacks and led the league with six forced fumbles. Over eight seasons, Watt accumulated 462 total tackles, 108 sacks, 33 forced fumbles, seven interceptions and seven Pro Bowl selections.

It’s clear the 30-year-old is crucial to the Steelers’ defense, and it’s equally clear several teams would be willing to trade a ton of picks for his services. Poles hasn’t operated that way at all, and there’s no reason to think he’ll start now. If Watt were a few years younger, maybe, but don’t expect a Mack 2.0 trade anytime soon.