Ahead of the 2018 NFL season, the Green Bay Packers were extremely aggressive in their pursuit of Khalil Mack, who was with the then-Oakland Raiders at the time and essentially forced the team to trade him by sitting out all of training camp.
Brian Gutekunst was in his first year as Green Bay's general manager and was willing to send the Raiders a first-round pick and several other selections to acquire the then-three-time Pro Bowler and 2016 Defensive Player of the Year.
The Packers, of course, were ultimately outbid by none other than the Chicago Bears, who sent a pair of first-rounders to Oakland, as well as a third-rounder and a sixth-rounder, and quickly signed Mack to a six-year, $141 million extension.
Mack ended up spending four seasons in the Windy City, earning three Pro Bowl selections and two total All-Pro nods in that time before being traded to the Los Angeles Chargers, with whom he spent the last three years, earning Pro Bowl selections every season.
While the future Hall of Famer just recently turned 34, he's still viewed as one of the top defensive players set to hit free agency. And there are many who believe the Packers are the best fit for him, including former Green Bay safety Matt Bowen, who now works for ESPN.
"The Packers adding Mack to pair with Rashan Gary would boost their pass rush off the edges," Bowen wrote recently. "Mack had six sacks and 41 pressures in 2024 with the Chargers. And even though he's turning 34 this week, he's still a three-down force with the steady play speed to heat up the pocket."
Green Bay does have the cap space to make this work, and adding Mack would undoubtedly be a strong move, as he would bring plenty of veteran leadership to a young roster.
But if a recent report is to be believed, Mack may prefer to take his talents elsewhere. And you've likely already guessed where that might be.
Khalil Mack reportedly has interest in a reunion with the Chicago Bears
Earlier this week, Chris Emma of 670 The Score, a popular Chicago sports radio station, reported that Mack is interested in a reunion with the Bears.
"Sources believe Mack has interest in a return to Chicago, where he played from 2018-21," Emma stated. "Mack isn't interested in the spotlight, but the vision would be for him to be a complementary piece of the defense, not the star."
Coming into this offseason, the Bears had big needs on the offensive line, which GM Ryan Poles has swiftly addressed by trading for both Joe Thuney and Jonah Jackson.
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One would think Poles is now ready to move on to priority number two, which seems to be finding an edge-rusher to play opposite Montez Sweat. And that's obviously where Mack comes into play, as the Bears could likely sign him to a one- or two-year deal.
Surely, the Packers can't lose the same guy to their archrivals twice, right?
Well, at this point, it actually seems quite possible, as Chicago is clearly ready to be aggressive to kick off the Ben Johnson era.
But even outside the embarrassment of once again watching Mack go to the Windy City, the Packers simply don't want to see this guy twice a year, as he's historically wreaked all kinds of havoc.
In nine career matchups against Green Bay — one with the Raiders, seven with the Bears, and one with the Chargers — Mack has racked up 8.5 sacks and three forced fumbles. So, Gutekunst may have to be just as aggressive to avoid losing him for a second time.
We'll find out soon enough where Mack ultimately lands, as the negotiating period begins on March 10.