It’s unlikely, really, that the 49ers brain trust of general manager John Lynch and head coach Kyle Shanahan is spending much time taking the advice of ex-players like DeSean Jackson on potential personnel moves. But that’s not stopping Jackson from weighing in on the team’s roster, especially a potential trade of fellow wide receiver Brandon Aiyuk.

After a successful couple of weeks plastering in some holes in the roster in the free-agent market, especially on the defensive side of the ball, with moves to bolster the front line and linebacker spots, the 49ers are facing the meat of their offseason. And the central question here is what to do with Aiyuk, the breakout star who established himself as one of the 10 or 12 best receivers in the game last year.

The 49ers will struggle to sign Aiyuk to a satisfactory new deal as he heads into his fifth-year option season. And for Jackson, that means sending Aiyuk elsewhere via a trade, perhaps to Pittsburgh, the team with which Aiyuk has been very publicly flirting this offseason.

"Let that man be free and go get a deal somewhere else."@DeSeanJackson10 on the trade rumors surrounding #49ers WR Brandon Aiyuk 👀@heykayadams pic.twitter.com/Ciz1CGQrEV

— Up & Adams (@UpAndAdamsShow) March 22, 2024

Brandon Aiyuk Making Steelers Overtures?

Jackson was speaking with Kay Adams on the “Up and Adams Show” podcast this week when the topic was broached. Adams pointed out that Aiyuk, who rarely posts on Twitter/X, tweeted at Steelers coach Mike Tomlin that, “They saying we twins. What you think?”

Jackson was of the mind that, whether it is the Steelers or another team, the 49ers should be prepared to send Aiyuk to another team.

“It’s gonna be hard for him to stay in San Francisco with him going into his fifth year, I don’t think they’ll be able to get a deal,” Jackson said. “It’s tough, man. Let that man be free and go get a deal somewhere else, man, because in your fifth year, you’re really supposed to go and get that extension.

“I don’t think he wants to go a whole other season to wait to go get another bag or go secure his bag. So I definitely see him trying to reach to get up outta there.”

Aiyuk is, technically, still under contract with the 49ers, on his $17.4 million fifth-year option. But he would almost certainly hold out for a new deal before he plays under that contract. Spotrac projects that Aiyuk’s market value is $24 million per year, or four years and $96 million.

Jackson could imagine Aiyuk in Steelers black. “If it is a fit—Russell Wilson, Justin Fields, they just lost, they traded Diontae Johnson to Carolina. They need another receiver. I definitely like that,” Jackson said.

49ers Want to Keep the WRs Together

It should be noted that all is not lost on the possibility of the 49ers re-signing Aiyuk. The team would need to restructure or move some other deals to create enough room for Aiyuk—the 49ers have about $10 million to work with this year, according to Over The Cap—and squeezing him in this season still might be only a temporary measure. But if the 49ers want one more crack at a Super Bowl with this group, they could make it happen.

Aiyuk racked up 1,342 yards on just 75 catches last year, and his 17.9 yards per catch were No. 2 in the NFL.

Lynch said back at the NFL draft combine that keeping Aiyuk won’t be easy, but it’s his intention to make it happen.

“We have some challenges,” Lynch said, per Pro Football Talk. “We have a lot of good players, a lot of good players who we’ve rewarded. Brandon’s one that we think incredibly highly of, one of my favorite guys around our building, the way he approaches the game. He’s a competitor. He’s a warrior. He plays with such physicality, also with grace, in the way some of the positions his body can get into.

“And then he’s got a flair for making plays when [they] matter most, and he’s served us very well as a franchise. And I think we’ve got a nice track record of extending the players that are important to us, and Brandon’s the guy we want to keep around for a long time.”