The most shocking move of the LA Chargers' offseason wasn't hiring Jim Harbaugh, it was trading Keenan Allen. Needing to free up salary to become cap compliant, the Bolts traded the veteran wide receiver to the Chicago Bears for a fourth-round pick.
Allen was unwilling to take a pay cut, even if that pay cut came via an extension, per general manager Joe Hortiz. As a result, the Chargers had no other option but to trade Allen and get whatever the team could in the draft.
Despite the lack of success in recent years, Allen was traded into a good situation in Chicago. The Bears just drafted Caleb Williams with the first overall pick and have a wide receiver corps that also includes D.J. Moore and Rome Odunze. If all goes as planned, the Bears will have one of the most exciting offenses in the sport.
As exciting as it looks on paper, there may still be a part of Allen who wishes he was still with the team that drafted him and an elite quarterback in Justin Herbert. This definitely seems to be the case after Bears OTAs, where Allen was spotted looking fairly disappointed at an underthrown pass from the first overall pick.
Keenan Allen looks like someone who misses Justin Herbert and the Chargers
One clip from OTAs does not tell an entire story but it is never a great sign when the camera audibly picks up a wide receiver sounding dejected after a throw from the quarterback. Williams is going to be just fine as an NFL pro but it may take some time until he is on the elite level that Herbert is currently on.
And by that time, Allen might already be on another team. Allen has not signed an extension with the Bears and while he seems open to a deal, it does not look like he is willing to take less for the security of an extension. If Chicago doesn't offer a market-value extension then Allen will likely test free agency.
Williams struggling in his first year as a pro would hurt Allen and his value in free agency. This is the last real chance for Allen to cash out on a big pay day and if his numbers dip in his new situation then he is going to lose out on money as a result.
If he was still in Los Angeles then he undoubtedly would have produced at a high level as long as he stayed healthy. Allen was having the best year of his career last season until he went on the shelf after Herbert's injury. There is reason to believe that he would have had a similar year in 2024 as Herbert's most-trusted weapon.
Instead, he now finds himself in a new offense with a new quarterback who is learning NFL speed as he goes. Allen has to now build a rapport with Williams that already existed with Herbert.
Chances are it will still work out fine for Allen and the Bears. But if there are any underthrown balls like this in game-action then the first person Allen is going to think about it Herbert.