Bears Cut Loose Caleb Williams’ Best Friend After Preseason Debut

According to the team’s official transaction wire, the Bears waived both Jackson and kicker Jonathan Kim on Tuesday from their 90-man roster in a series of roster moves.

The Chicago Bears made a move that caught fans’ attention this week, releasing wide receiver John Jackson after his preseason debut. While roster cuts are a normal part of the NFL grind, this decision carried an emotional weight — Jackson is not just any player, but one of rookie quarterback Caleb Williams’ closest friends.

For Williams, the transaction wasn’t just a footnote on a depth chart. It was personal. “The NFL is a business — but no cut can break the brotherhood John Jackson and I built,” Williams said, his voice steady but tinged with emotion. That single line captures the complexity of life in the league: fierce competition mixed with deep bonds forged through shared dreams and relentless work.

Williams and Jackson first crossed paths years ago, their friendship blooming long before either wore Bears colors. They’ve trained together, celebrated together, and pushed each other through grueling offseasons. Jackson, known for his work ethic and locker-room presence, had been battling for a roster spot, making his preseason debut with the hope of earning a role in Chicago’s receiver rotation.

Despite his limited reps, Jackson showed flashes of the quickness and reliable hands that had made him a trusted target for Williams in practice. But the NFL’s roster math is unforgiving. With teams needing to cut down to 53 players, every decision comes with casualties, and this one hit especially close to home for the Bears’ new franchise quarterback.

Fans were quick to react online, with many expressing sympathy for both men. Some argued that Jackson’s chemistry with Williams could have been an asset during the regular season. Others pointed out that this is the reality of professional football — every week, promising players see their opportunities vanish in an instant.

Williams, however, made it clear that while their professional paths may diverge, their connection runs deeper than football. “It doesn’t matter what uniform we wear next,” he said. “We’ll always have each other’s back.”

As the Bears continue their preseason preparations, Williams will have to adjust to working with a new set of receivers. For Jackson, the journey isn’t over — other teams could take notice of his skills, and the door to a comeback remains open.

For now, the story of Williams and Jackson is a reminder that behind every roster move is a human story — one of friendship, resilience, and the kind of loyalty that no transaction can erase.

Jackson caught just one of his four passing targets in Sunday’s exhibition game against the Miami Dolphins, dropping a wide-open pass from quarterback Austin Reed in the final 25 seconds that would have given the Bears possession near the 31-yard line and allowed them to attempt a game-winning field goal. Instead, they settled for a 24-24 tie.

Jackson received the Bears’ third-worst offensive grade (36.3) from Pro Football Focus, finishing ahead of tight end Durham Smythe (29.3) and guard Chris Glaser (34.2).

The Bears also waived defensive back Major Burns with an injury designation, placed veteran cornerback Shaun Wade on the season-ending injured reserve list and signed defensive backs Millard Bradford, Mekhi Garner, Kaleb Hayes and Mark Perry.

John Jackson & Caleb Williams Are Friends From USC

Jackson and Williams have been friends for several years. Both played for USC during the 2022 college football season, the year in which Williams won the Heisman Trophy. Jackson has also characterized Williams as “probably my best friend” in the past, which carried a slight air of optimism about his chances of making things last with the Bears.

Unfortunately for Jackson, one lousy preseason performance cost him his latest chance.

Jackson hadn’t faced an easy path to cracking the Bears’ 53-man roster at wide receiver. The Bears likely only have one roster spot available behind D.J. Moore, Rome Odunze, Luther Burden III, Olamide Zaccheaus and Devin Duvernay, all of whom are virtual locks to make the team. And to gain ground, Jackson needed a standout first game.

Instead, undrafted rookie Jahdae Walker (three receptions, 41 yards) and Maurice Alexander (four receptions, 19 yards) made the stronger impressions. Both caught touchdown passes against the Dolphins, with Walker’s 15-yard over-the-shoulder grab standing out as one of the Bears’ best highlights from their preseason opener.

With Jackson gone, the competition for the No. 6 receiver role has narrowed. Walker and Alexander have improved their cases, but Tyler Scott (2023 fourth-round pick), rookie JP Richardson and ex-Green Bay Packer Samori Toure are also in the hunt.

Will Bears Sign Another K to Replace Jonathan Kim?

The Bears have gone back down to just one placekicker on the 90-man roster, but it is unclear at this point whether they will stay that way or sign someone to replace Kim.

The Bears will count on veteran Cairo Santos as their primary kicker for a sixth straight season in 2025, but they have traditionally kept another kicker on their practice squad for emergencies in the past. Teams also tend to carry multiple kickers on their roster in camp to avoid overloading their starter with every rep in practice and the preseason.

Kim, an undrafted rookie, seemed like a solid bet to win the No. 2 job after hitting both of his extra points against the Dolphins, but the Bears were clearly not sold on him.

Does that mean they will sign another kicker before their next preseason game against the Buffalo Bills next Sunday night? Not necessarily, as they could just as easily find a suitable No. 2 option during the roster cutdown and stash him on the practice squad.

Even still, don’t be surprised if another kicker joins the ranks in the coming days.