It was the middle of the night when Howie Long realized his son’s career was ending. There, cooped up in a Los Angeles hotel room, Howie stayed by Kyle’s side as the Bears lineman recovered from simultaneous surgeries to repair his elbow and fix a torn labrum in his shoulder. Everything in the hospital went smoothly. Back at the hotel, less so. 

“I remember just following him around the hotel room that night, throwing up probably 30-35 times,” Howie said. “It was a brutal night. To watch your kid go through that is a challenge.”

The Longs are no strangers to the surgical table; if they’re not the most decorated family in NFL history, they’re definitely the most operated-on. Howie had 11 surgeries during his Hall of Fame career, Kyle’s gone under the knife a half-dozen or so times, and Chris missed 10 weeks in 2014 after an ankle procedure. Knowing that, there’s a cruel irony in the fact that Kyle’s NFL career ended 24 hours after being on the field for 100% of the offensive snaps. “The writing was on the wall. There was no secret there,” he said. “I wasn’t able to fulfill my end of the bargain."

It’s easy – and probably lazy – for anyone to claim that they could see the end coming from a ways away. Kyle came into 2019 healthier than he’d been in some time – one more season removed from a 2016 ankle surgery that, according to Howie, was “actually a three-year injury.” He had his legs under him again, but four years of season-ending injuries leaves a mark. And for what it’s worth, lining up against All-Pros throughout the summer didn’t make the decision to retire any more difficult.  


“It became clear to me in practices against Akiem [Hicks],” Kyle said. “We used to never dial back. And Akiem is a freakshow, and he was a great guy when we played together. Towards the end of my career, he would dial it back as not to embarrass me in practice.” 

Long probably could have extended his career elsewhere, but for someone who grew up staring at only one framed, silver-and-black jersey (and also a “friggin’ gold jacket”) in his childhood home, loyalty is important. As he sees it, only one team drafted him, paid him, and chose not to cut him after any of the four IR trips. Yes, the NFL is a cold business, something he found out early in his career when that same team cut his best friend, Jordan Mills, and then moved him into Mills’ position. But standing by him through injured season after injured season left a lasting impression on Kyle, and if anything, the Bears’ fidelity only made it that much easier of a decision. 

“Maybe I'll come back in another capacity one day,” he said. “[Matt] Nagy, [Ryan] Pace and I have had that conversation.

“We’ve all been in that relationship where the hints and the signs are clear -- not red flags, but the communication is clear and honest,” he said. “That’s all you can ask for in a relationship. I wasn’t the ex-boyfriend who stuck around and said, 'I can be better. I love you.' That wasn’t me. I love you, but I love you so much I’m going to leave you alone.” 

And so, after seven years and three Pro Bowls, Kyle Long left the Bears alone. The immediate weeks following the break-up were hard, and he credits fellow alum Olin Kreutz for being an invaluable resource during the toughest stretches. Not long after Kyle went on IR, it was Kruetz who reached out, suggesting that they start working out together. “Football is my life,” Kyle said. “Olin gave me an opportunity to wean myself off of it … I don’t know what I’d be doing right now if I didn’t have a place like that to go to.” The two spent their mornings with MMA trainers, and the results speak for themselves: Kyle certainly doesn’t carry the weight of an NFL lineman anymore, and according to Chris, has lost close to 60 pounds. When Kyle returns to Chicago on a more full-time basis, the plan is to pick up the workouts again.

Retirement is never easy in the NFL, but it helps when both your dad and brother have already done it – and rather gracefully, at that. Howie has been a successful studio analyst at Fox Sports for years, and Chris has become an award-winning humanitarian since walking away after the 2018 season. Retiring was an easy decision for Chris, but he did admit “I only miss game day... It’s a once in a lifetime opportunity to make 65,000 people go nuts.” Both are at peace with stepping away when they did, though, and Kyle relied heavily on that confidence when making his own decision. 


“You know, a lot of the advice and things I lean on [them] about are, more often than not, non-football things,” Kyle said. “Because football comes naturally to me, and that's one thing I really understand. A lot of things, like any kid or brother or son has to deal with, are certain life problems and issues we all face. And who better to ask than your brother or your dad?” 

For instance, it was his brother who emphasized to Kyle the importance of staying busy in retirement. After two decades worth of endless commitments, flipping the switch and having far more time for yourself isn’t always the answer. 

“You would think not being stressed and not being busy would be good for you, but for a lot of guys it’s that existential crisis of, ‘What’s my purpose now?’,” Chris added. “So you’ve got to fill it - you’ve got to find something that you’re passionate about.”

Kyle isn't exactly sure what he’s passionate about – at least not yet. A well-earned vacation was in order, and he plans to be in Chicago more often now that the season has officially ended. For now, perhaps the easiest place to find him is on the live-streaming app Twitch, where his Bears game broadcasts have become wildly popular with fans and media members alike. As for his next paid gig? He conceded that being related to multiple famous athletes-turned-media-members (Chris also hosts a podcast on The Ringer) has its benefits, one of which allows for the obvious pivot into some form of media. It wasn’t surprising to see him spend a few days co-hosting David Kaplan’s radio show this week. 

“What’s next for me is figuring out who the heck I am,” he said. “I feel like I’ve been in one place for so long, it’s time to branch out and figure out what the heck’s up with this great big world we live in.”