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Jimmy G to the 49ers: That Halloween Trade That Haunted Them For Years

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San Francisco 49ers logo on gradient background — Created by the Sports On Tap desk | Source : Sports On Tap (team logos property of their respective owners)

The San Francisco 49ers are currently dealing with a bunch of injuries, but with most players expected back, you know they’re still eyeing the trade market for that “missing piece” to put them over the edge before the November 10 deadline. It’s nothing new, really, ’cause Kyle Shanahan’s crew has a knack for making those blockbuster midseason moves when they think they’re close.

Shanahan’s Midseason Gambles and the Hunt for “The Guy”

The Niners love a good midseason trade, especially when they feel like they’re just one player away from greatness. With their current injury situation in 2026, the speculation is already heating up about who they might target. But before we get ahead of ourselves, it’s worth taking a look back at some of Shanahan’s notable midseason plays. And when you talk about those, you gotta talk about Jimmy Garoppolo.

Jimmy G: The ‘Future’ That Never Quite Was

Remember that fateful Halloween day in 2017? That’s when the 49ers made their move for Jimmy Garoppolo, snatching him from the New England Patriots for a second-round pick. Man, some people have revisionist history about Jimmy G’s time in San Fran, talking about boneheaded picks or stepping out of bounds. But back then? He was seen as the future, no joke.

He was drafted by the Patriots in 2014, playing backup to Tom Brady and widely considered the heir apparent. He even looked “very impressive” in 1.5 games in 2016 filling in for a suspended Brady before, you guessed it, getting injured. Seems like that was a running theme. By 2017, everyone wanted him, even the Cleveland Browns, but the Patriots wouldn’t budge. Then, BOOM, the 49ers got him.

Their quarterback room at the time was Brian Hoyer and rookie C.J. Beathard, who was starting for an ineffective Hoyer. Most folks thought Kyle Shanahan was gonna snag Kirk Cousins the following offseason anyway. Jimmy G was just seen as a backup plan or, at best, a quick rental to see what he had. Coming in midseason as a starter is always tough, especially switching from the Patriots’ Erhardt-Perkins system to Shanahan’s West Coast terminology. But Week 12 sped things up: C.J. Beathard got injured in the final minute of a home game against our Seattle Seahawks. The Niners were up 24-6 at that point, and suddenly, Garoppolo was in. He ended up staying on the roster until 2022.

So, while Shanahan’s crew speculates on *their* next “missing piece” for 2026, it’s worth remembering how these midseason gambles can play out. Sometimes, the heir apparent isn’t quite so apparent after all.

This article was created with AI assistance and published under Seattle On Tap’s editorial standards. See our Editorial Policy.

Originally reported by Niners Nation.

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