BOURBONNAIS, Ill. — It’s not like Bobby Massie signed for cheap when he and the Bears agreed on a four-year extension back in January. The contract guarantees the right tackle $14.5 million, with a $5.2 million signing bonus and a maximum value of $30.8 million (though it’s structured to give the Bears an out after the 2020 season). 

But Massie could’ve became an unrestricted free agent and tried to maximize the value of what probably was the 30-year-old’s last big contract. Seven tackles were guaranteed over $10 million in free agency in 2017, and while 2019’s free agent class was more top-heavy, there certainly would’ve been a market for a reliable veteran as an alternative to high-priced signings like Trent Brown (four years, $36.25 million guaranteed) and Ja’Wuan James (four years, $32 million guaranteed). 

The point: Quality offensive line play often commands top dollar on the free agent market. Massie, though, wasn't interested in chasing cash in March, opting for job security in January. 

“I made a lot of money already," Massie said. "And what’s the point of going somewhere else, to a losing team and or even to a winning team somewhere that I don’t like or don’t feel comfortable just for a few extra dollars?

“Because really at the end of the day, how much money do you really need? You know what I mean? I’m happy here.”

Retaining Massie was the first major move executed by Ryan Pace after the Bears crashed out of the playoffs following their 12-4 NFC North-winning season. His extension, coupled with Kyle Long agreeing to restructure his contract, meant the Bears were able to retain the same five starting offensive linemen who took the field against the Philadelphia Eagles in January. That continuity is important, especially given how well Harry Hiestand’s unit fared last year, specifically in pass protection.


The Bears were the second-most efficient pass blocking offensive line in the NFL in 2018, per Pro Football Focus, and only the Baltimore Ravens’ offensive line was credited with allowing fewer sacks than the Bears’ 11. No offensive line allowed fewer pressures than the Bears’ 117. 

And Massie was a critical part of those efforts. He was charged with allowing only one sack on 635 pass blocking snaps, per Pro Football Focus — making him the only tackle with over 600 pass blocking snaps to allow just one sack. 

Those are all numbers that could’ve wound up in his agent’s pitch to interested teams. 

“There’s scenarios where guys sacrifice maybe a little bit of money to be here with guys they want to play with, coaches they want to play for, an organization they want to be part of,” coach Matt Nagy said. “That’s just who he is and I think it speaks volumes about him.”

Massie was an early believer in Mitch Trubisky and now gets to practice against Khalil Mack in training camp (“He just makes me better because I’m not going to see too many players like that coming up this season,” Massie said). He saw what the bad years with the Bears looked like in 2016 and 2017, and felt like leaving after 2018’s turnaround wouldn’t have been right for him. 

Massie, too, got married in July. The stability he’s found in Chicago is hardly a given for NFL players. And he’ll continue to enjoy that stability for a few more years while playing on a team with guys he likes, one he believes has much more success ahead of it. 

“We’ve come to build something here,” Massie said. “I love it in Chicago. I’ve been here for the rough days, and we’ve turned things around here in a major way and I just didn’t want to leave on that note. I’ve just built relationships with a lot of people here and I wasn’t ready to leave.”