Kyle Long and the Chicago Bears: Three Pro Bowls, Four Surgeries, One Hell of a Career
The Long Family and the Road to Chicago
Kyle Long’s father is in the Hall of Fame. His brother Chris was the second overall pick in 2008 and won two Super Bowls. His younger brother Howie Jr. works in the Raiders’ front office. By the time Kyle arrived in Chicago as the 20th pick of the 2013 draft, the expectation wasn’t just that he’d make the NFL – it was that anything less than excellence would feel like a disappointment for a family where the baseline is Pro Bowl.
He cleared that bar in year one. Then year two. Then year three.
What makes his story worth reading isn’t the pedigree, though. It’s that Kyle Long got to Chicago through Saddleback College – a junior college in Mission Viejo, California – after leaving Florida State and switching positions entirely, from defensive end to offensive line. One season at Oregon after the transfer. Four games started. Then the NFL called.
Howie Long played 13 years for the Raiders and was inducted into Canton in 2000. Chris earned the Walter Payton Man of the Year Award in 2017. Kyle’s path was rougher and stranger than either of theirs, which is probably why Bears fans took to him the way they did. He felt earned.
What He Was at His Peak
During the pre-draft visit to Halas Hall in 2013, offensive coordinator Aaron Kromer showed Long film of exactly one player: Ndamukong Suh. No highlights package, no variety. Just Suh – one of the most terrifying defensive tackles in the league at the time. Long recalled the message landing clearly: we’re not drafting you because you played well in college. We need someone who can handle monsters.
He handled them immediately. In his rookie season, Long gave up two sacks on 1,079 snaps. Two. He made the Pro Bowl that year, becoming the first Bears offensive rookie to do so since Gale Sayers in 1965. Then he made it again in 2014, this time earning second-team All-Pro honors from the Associated Press. Then again in 2015, when the Bears moved him from right guard to right tackle mid-career and he held his own at a position he hadn’t played regularly.
Three consecutive Pro Bowl selections in the first three seasons – that had happened only seven times in Bears franchise history before Long did it. The last Bears player to earn back-to-back Pro Bowl nods before him was Brian Urlacher, from 2000 to 2002.
Pro Football Focus had him on their All-Rookie Team in 2013. What stood out on film wasn’t just power – it was his feet. Guards that size are supposed to be slow getting to the second level. Long wasn’t. He had genuine athleticism, which is partly why the Bears thought they could move him to tackle when they needed to, and why he made the Pro Bowl at two positions.
Forty-seven of his 77 career games came in those first three seasons. When he was healthy and playing every week, the Bears had one of the better right sides in football.
2016: The Ankle That Changed Everything
Week 10, November 13, 2016. Bears versus Buccaneers in Tampa. Long had already been playing through a torn labrum in his left shoulder for seven games when he injured his right ankle badly enough to be carted off the field. Placed on injured reserve November 15. Season over.
He’d also missed Week 8 with a strained triceps. So by mid-November of that year, Long had played through a torn labrum, missed a game with a triceps strain, and then ended his season on a stretcher with an ankle injury that required surgery. That’s three separate serious issues in one season.
He told the Chicago Sun-Times years later that he heard the metaphorical train coming that fall. The ankle injury wasn’t the moment he consciously admitted his career was in trouble – he says he ignored the signal – but looking back, he calls it the turning point. “It unmistakably signaled the end,” he said. At the time, he was 27.
The next four years went like this: 2017, placed on injured reserve in December after aggravating the shoulder in Week 13, with ankle and finger problems throughout. Neck, shoulder, and elbow surgeries in the offseason. 2018, started the first eight games before a foot injury in Week 8 sent him to IR in November; activated for one game in Week 17. 2019, suffered a hip injury in practice ahead of Week 4, missed the Vikings game, came back to play every snap in London against the Raiders in Week 5, then the Bears shut him down for good. IR for the fourth straight season.
From 2016 through 2019, Long played in 30 regular-season games total. In his first three seasons, he’d played 47.
Retirement, Then Kansas City, Then Retirement Again
January 6, 2020. Long posted on Twitter: “Some Chicagoans are probably happy to hear I’m finally stepping away and getting my body right. Some Chicagoans may be sad to hear this. Either way u feel about it, I want u to know how lucky I am to have spent time in your city. I became a man while playing in Chicago.”
When someone pointed out he was leaving, he replied: “I was drafted a Bear and I decided to retire a Bear. Not many can say that.”
The Bears had already declined his 2020 contract option – he was scheduled to make $9.6 million – making him an unrestricted free agent on March 18. General manager Ryan Pace said the team thought “the world of him.” The language on both sides was careful and warm in a way that usually means the situation was more complicated than it looked from outside.
Long spent 2020 as a studio analyst for CBS Sports Network’s That Other Pregame Show alongside Amy Trask, Adam Schein, and London Fletcher. He also worked with Amazon’s Twitch platform on an NFL show and started hosting a weekly program on NASCAR’s YouTube channel. He appeared to have landed well.
Then in March 2021, the comeback. ESPN confirmed he planned to return to the NFL. He visited the Las Vegas Raiders – his father’s old team – and then signed with the Kansas City Chiefs. He told reporters the year off had restored his desire for the game. The Chiefs had just lost the Super Bowl and needed offensive line depth.
He never played a game for Kansas City. A leg injury complicated the comeback, and he retired for the second and final time in 2022. He spent that Chiefs season listed on their roster without suiting up, which is a strange footnote for a career that deserved a cleaner ending – though Long himself never seemed to frame it that way publicly.
What His Bears Career Actually Meant
The honest assessment: Long’s peak was real, it was brief, and it was genuinely great. Three Pro Bowls and an All-Pro in the first three seasons is not a small thing. The fact that it happened while the Bears were bad – 8-8 in 2013, 5-11 in 2014, 6-10 in 2015 – made him one of the few players Bears fans had legitimate reason to watch during those years.
His teammates voted him the Ed Block Courage Award in 2018, which goes to the player who best exemplifies perseverance and sportsmanship in the face of adversity. That vote says something. The offensive line is a small, specific world, and the men in it knew what Long was going through to keep showing up.
What I find genuinely strange about Long’s career is the timing mismatch: he was at his best when Chicago was building toward something, and he was hurt when they got there. The 2018 Bears went 12-4 and made the playoffs. Long started eight games that year before the foot ended his season. He came back for the wild-card loss to the Eagles – the game where his brother Chris was playing on the other side – and started. The Bears lost 16-15 on a missed field goal. That game, with both Long brothers on the field and their father watching from the Fox broadcast booth, might be the most concentrated version of everything complicated about Kyle Long’s time in Chicago.
He signed a four-year, $40 million extension in 2016 with $30 million guaranteed. The same offseason the ankle blew up. The Bears paid most of that money to a player who appeared in 30 games over the next four years. That’s not a judgment on Long – it’s just the economics of how NFL injuries work – but it shaped how the front office and fan base remembered his later years.
Historically, among Bears offensive linemen, Long belongs in the conversation with the franchise’s best at guard. The three-year run from 2013 to 2015 holds up. What would have happened without the ankle injury in Tampa is unknowable, but the trajectory before that point was pointing somewhere significant.
Life After the Bears
Long lives in South Florida now with his wife and two daughters. He co-hosts Pushing the Pile with his brother Chris. He’s appeared multiple times on the Bears’ own podcast, Bears Etc. with Jeff Joniak and Tom Thayer, offering analysis on the current roster and reflecting on his own career. As recently as 2025, he was on that show talking about the direction of the franchise under Ben Johnson.
The NASCAR work was genuinely his own interest, not a brand deal someone arranged. Long is a part-owner of Mode Motorsports in the eNASCAR Coca-Cola iRacing Series and co-hosted a weekly show on NASCAR’s YouTube channel. It’s a specific enough corner of sports fandom that it reads as real.
He’s stayed connected to Chicago in a way that some departed Bears haven’t. That matters to a fan base that felt the injury years as a kind of ongoing grief – watching someone that talented spend so much of his career hurt.
Long was 31 when he first retired. His best football was behind him by 27. That gap is the whole story.
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