One of the easiest ways to tell whether a team really believes in a player is the price it’s willing to pay to keep him or get him. That’s the conversation surrounding Garrett Wilson right now, and it’s the same kind of bet the Bears just made when they acquired Jeffery Simmons for a package built around first-round picks.
Simmons had just signed a three-year, $105.8 million extension this past summer, and on Thursday morning he was sent to the Chicago Bears for a 2027 and 2028 first-round pick. The Titans also included a fourth-rounder this year, while the Bears sent back a 2028 fifth-rounder. It’s the sort of move a team makes when it believes a premium player is worth more than multiple swings in the draft.
That’s the lens for the San Francisco 49ers if they want to chase Wilson from the New York Jets. Wilson signed a four-year, $130 million extension in July 2025, and the Jets sit at 2-5. If the 49ers want to get aggressive, the argument starts with whether Wilson is worth the kind of haul that would force New York to think beyond the short term.
The Jets would not move him cleanly. Trading Wilson would leave dead cap behind, according to Over the Cap: $6.75 million through 2029 and $4 million in 2030. That kind of figure is exactly what Jets fans would point to as a reason to hold the line.
But there’s another side to the ledger. Moving Wilson would also open up real money.
The Jets would save $16.5 million in 2027 and more than $29 million over the next two years. And for a team already projected to have the third-most cap space next year, with over $85 million even with Wilson on the books, that flexibility matters.
The draft capital angle matters too. The Jets already have three first-round picks in the 2027 draft.
Adding another would give them even more ammunition to try to replace Wilson, especially with the possibility that they use one of those first-rounders on a quarterback in 2027. That’s the sales pitch: they can keep moving the ball without Wilson, then use the extra picks to reshape the roster.
And Wilson isn’t exactly hiding from the situation. On Wednesday, he said he didn’t want to be traded, but he does want to win. Offensive coordinator Frank Reich called Wilson’s frustrations “ a healthy tension ” on Thursday.
From San Francisco’s side, the case is even simpler: this is not the moment to get cute. Trent Williams is 38.
George Kittle is 33. Mike Evans is 33.
DeForest Buckner is 32. Christian McCaffrey is 30.
Nick Bosa’s body is still a question mark. Fred Warner, a year removed from being the ultimate Ironman, missed double-digit games because of a freak accident and turns 30 in November.
That’s why the 49ers would be foolish to assume this version of the team can survive another 20-plus game season after this one. And unlike a middling receiver move, Wilson changes the math.
He already topped 1,000 receiving yards in his first two seasons with Zach Wilson throwing him the ball. He can win on the route tree, beat corners off the line, and make the kind of contested grabs that shift a game. The route where he gets separation is never the only route he can run.
For the 49ers, this wouldn’t be about developing a receiver from scratch. It would be about buying certainty.
Wilson would become the future of the offense, and that future would come without a learning curve. He fits the kind of player a Kyle Shanahan offense would dream up in a lab.
That’s also why the move would serve as more than just an upgrade. It would help the 49ers put the Brandon Aiyuk mess behind them, reduce the pressure of wondering whether Ricky Pearsall stays healthy, and avoid putting too much on De’Zhaun Stribling to replace Evans down the road.
The 49ers’ first-round track record under this regime doesn’t compare to a player like Wilson. That’s the real appeal here: no guessing, no hoping a rookie becomes a star, just a prime-age difference maker who is already there.
It’s a rare opportunity for a team like San Francisco to go after a player entering his peak while he’s visibly unhappy. Whether the Jets would actually open the door is another matter entirely, but if the 49ers are serious about pushing all their chips in, Wilson is the kind of target that makes the gamble worth discussing.
In Other News...
49ers Trade Could Already Be Bad News For Jordan Watkins
The 49ers move to bring DeForest Buckner back to San Francisco bolstered one side of the ball, but it also has a ripple effect elsewhere on the roster as the trade deadline approaches. For a team already trying to keep its offense balanced, any new addition can change the math, and that is where Jordan Watkins enters the conversation. The rookie receiver has been part of the mix, but his role is hardly locked in with the 49ers still navigating their passing-game plans.
San Francisco has been connected to more help at wide receiver, and that kind of talk always creates pressure on the players fighting for snaps. Watkins has flashed enough to stay in the picture, but if the 49ers do make another move for a pass catcher, the competition for playing time could get even tighter. For now, he remains one of the names to watch as the front office weighs how aggressive it wants to be before the deadline. [Read more 🡒]
49ers Face An Uncomfortable Mac Jones Reality As Deadline Nears
Mac Jones has become one of the quieter names in the trade chatter around the 49ers as the NFL deadline draws closer, and that silence says plenty. Despite the speculation that always follows a backup quarterback with a recognizable track record, no real market has developed for Jones, leaving San Francisco in the familiar position of carrying a passer whose value around the league has not matched the buzz around him.
With the deadline set for Nov. 10, the most realistic outcome now looks like Jones simply staying put and seeing out his contract in San Francisco. The one thing that could change the picture is a major injury to a playoff contenders starting quarterback, which would suddenly turn a backup into a far more urgent target, but until something like that happens, there is not much reason to expect movement. [Read more 🡒]
49ers Face A Second-Half Decision These Fill-In Standouts Earned
The Week 8 bye should bring a familiar wave of reinforcements back to the 49ers, with key names like Nick Bosa, Deebo Samuel and Mike Evans expected to rejoin the lineup. But the break also handed San Francisco a reminder that some of its depth pieces have done more than merely hold the fort. Jordan Watkins has settled in at wide receiver, Kaelon Black has chipped in as a runner with a touchdown, and Gracen Halton has made his presence felt on defense when the 49ers needed answers.
For Kyle Shanahan, the tricky part now is figuring out how much of that production deserves to stick. Watkins has earned a bigger look after handling a heavy workload before the bye, while Black's burst gives the backfield another option worth keeping active. Halton, meanwhile, has turned momentum plays into real pressure, and with the starters coming back, San Francisco has a second-half rotation decision on its hands that could shape more than just the next game plan. [Read more 🡒]