Which offseason move with the 49ers regret the most?

Which offseason move with the 49ers regret the most?
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The San Francisco 49ers roster is set. Until they make three or four more moves this week. In this post, we’ll play the hindsight game ahead of the regular season and talk about which moves the Niners will regret a month or three by now. Here are the four “regrets,” and you can decide at the end.

Trading Jordan Mason

Mason might have been the top answer before the 49ers acquired running back Brian Robinson. San Francisco traded Mason away because they didn’t want to pay their RB2 significant money. Isaac Guerendo and a rookie (which turned out to be Jordan James) could theoretically provide the same benefit as Mason did at 80 percent of the cost.

Mason’s cap number in 2025 is $2.25 million. Robinson’s is $3.4 million. Once the dust settles, the salary cap difference is minimal, but the process of trading Mason only to bring back a similar player felt off after Guerendo and James suffered injuries. If Robinson produces at an RB2 level, the Mason trade will be moot.

Not adding more wide receiver help this offseason

Technically, the 49ers did add wide receivers this offseason in Jordan Watkins and Demarcus Robinson. They were also expecting last year’s fourth-rounder, Jacob Cowing, would also produce in Year 2. Unfortunately, both have injuries that put their status to start the season in question.

The team may have felt blindsided by Jauan Jennings’ contract request, but there was no way to know he’d miss all of training camp and the preseason with a calf injury. Although there were names on the roster, there were no “NFL” wide receivers on the roster, if that makes sense. Hence, the trade for Skyy Moore — who also leaves a lot to be desired.

San Francisco signed Marquez Valdes-Scantling and could have Kendrick Bourne on the roster by the time you read this. Robinson has stud potential in this offense. We’ll just have to wait a month to see it. It feels like a short-term complaint about wide receivers because of Robinson’s suspension. But were the Niners naive in thinking these smaller wideouts could stay healthy?

Failing to bring in another offensive lineman

Heading into 2025 with Ben Bartch penciled in as the starter looks great on paper, until you see his injury history and acknowledge that he has already been banged up in August. That meant, once free agency passed, you’d be relying on a rookie if Bartch went down.

We knew the 49ers would have a heavy defensive draft. They’ve also had success hitting on offensive linemen on Day 3 of the draft. However, asking a seventh-rounder, Connor Colby, to be a plug-and-play starter is impossible. Colby and Drew Moss are the backups. Matt Hennessey was a new addition...