New Bears wide receiver Keenan Allen is going to be playing for a team not named the “Chargers” for the first time in his eleven-year NFL career. Allen was shipped to Chicago back in March in exchange for a fourth-round pick that Los Angeles used to trade up and select Georgia wide receiver Ladd McConkey in the second round. Because Allen was a trade asset, the Bears are now faced with contract concerns in their new weapon’s future. 
Allen arrives in Chicago with only one year remaining on his previous four-year, $80.1MM deal. Because of that, Allen is either heading for free agency for the first time in his career or finding a way to extend his contract with the Bears. Either way, Allen is preparing for the future, hiring new agents in anticipation of the contract situations ahead, per Tom Pelissero of NFL Network.
After playing out three years of his rookie deal out of Cal, Allen signed a four-year, $45MM extension, avoiding free agency. Before that deal could expire, the Chargers extended him again on his most recent four-year deal. If he fails to extend his contract in Chicago, he will hit NFL free agency for the first time. He has a lot that he can prove in a potential contract year. At 32 years old, Allen will try to put up career numbers for the second year in a row but will do so this time with a rookie quarterback. He’ll also be competing for targets with D.J. Moore, who showed how dominant he could be as Chicago’s WR1 last year.
The other option sees Allen enjoying a multi-year stay with the Bears. Allen may utilize his new representation to avoid free agency once again and sign an extension to stay in Chicago. This is a route that Allen has claimed to be open to with the Bears but one that he failed to see through this past year with the Chargers, who reportedly offered him another extension to stay in Los Angeles.
Perhaps the change in representation marks a change in contract year strategies for the veteran pass catcher. Maybe instead of continuing to extend his contracts before they expire, Allen has the intention of finally testing the free agent market and hired new agents to handle the situation. Only the future will tell.
I’m certainly a fan of Keenan Allen and he will bring some much needed leadership to the Bears locker room but multi year contract extensions for 32 yr old WRs is something I’d probably balk at unless the guy was a Jerry Rice or Larry Fitzgerald kind of player.
I’ll add Randy Moss to that list.