20. Drew Bledsoe
Tom Brady blazed out of nowhere to leave the Patriots in an enviable position. They had a franchise-defining choice ahead of them. They could make a recuperated Drew Bledsoe their starter again. Or they could fully back Brady and make him their franchise quarterback. Bledsoe was one of the league’s better signal-callers, so this wasn’t a clear-cut call.

In the end, they reached a deal with the Bills to trade Bledsoe. It was a blockbuster deal that saw the Pats receive a first-round pick in exchange. The Patriots were the clear winners because of Brady’s magnificent career. He won six Super Bowls in New England. Meanwhile, Bledsoe never even made the postseason during his time in Buffalo (via Sporting News).