Jimmy Garoppolo
In 2018, the 49ers swooped to snatch ‘Jimmy G’ from the Patriots. This came against Bill Belichick’s wishes because he wanted to keep the quarterback. Garoppolo impressed in flashes for the franchise and Belichick reportedly saw him as Tom Brady’s long-term replacement. The problem was that it seemed like Brady wasn’t going anywhere soon.

Finally, the Patriots agreed to send him west in exchange for a second-round pick. It was a relatively good deal because Garoppolo became their starter for the next half a decade. However, he never convinced everybody that he was the answer. Yes, they had a Super Bowl appearance with Jimmy G. under center but he was far from the best in the league (via Bleacher Report).