3. NY Jets trade for Tim Tebow in 2012
The infamous Tim Tebow trade earns a spot on this list not because of the draft capital it took to acquire him (it wasn't much), but because of how horrendous the move seemed at the time.
It was one of those moves destined to fail from the start, up there with the drafting of Christian Hackenberg and the hiring of Adam Gase.
Tebow was fresh off his historic, miracle run with the Denver Broncos, but following the signing of Peyton Manning, Denver decided to ship him away to New York, instantly creating a circus of controversy.
That controversy only grew with Mark Sanchez and the Jets struggling. Fans cried for Tebow to replace the former sixth overall pick, but the Jets preferred to use him on special teams and as a wildcat quarterback.
In total, Tebow played just 12 games for the Jets completing 6-of-8 passes for 39 yards while rushing another 32 times for 102 yards.
His impact was minimal on the field, but off the field, his presence alone was enough to make the Jets somewhat of a laughing stock with countless disparaging headlines.
The Tim Tebow experiment was a complete failure, and while the Jets didn't give up much in the way of draft capital (as compared to other entries on this list), this was a trade that never should have happened in the first place.