The Chicago Bears get Jimmy Garoppolo for a pair of picks
This first deal is pretty straight forward. The 49ers once traded a second-rounder for Garoppolo when he was a member of the New England Patriots. At that point, he was a pretty highly-touted youngster whom Bill Belichick was grooming to potentially replace Tom Brady.
However, we all know how that story ended. Brady wasn’t anywhere close to done, so the Patriots moved on from Garoppolo and netted that second-round selection. At this point in his career, and coming off an injury, Garoppolo wouldn’t fetch a second-rounder — at least, he shouldn’t.
The Bears could opt to deal a third and fifth-round pick in exchange for Garoppolo, which would mean they get to keep their first and second-rounders, thankfully. Last year, the Bears didn’t own a first-round pick, then picked twice in the second round before not picking again until the fifth.
Similarly this year, the Bears would pick in the first two rounds, but then have to wait until the sixth round to pick again. Last year, they dealt a fourth-round pick in the trade to go up and get Travis Gipson.
Skipping three rounds in this year’s draft would be difficult. But, getting an experienced veteran quarterback who is (yes, he is) an upgrade over Mitchell Trubisky and Nick Foles could be worth the risk.