Last Game: 2016
Who’s Still Paying Him: Bears
How Much They’re Still Paying Him: $2 million this season

The Bears paid Cutler about $90 million after acquiring him from the Broncos in 2009. And he was always just good enough to contend, but never good enough to actually win anything of consequence. Chicago made the playoffs just once with Cutler at quarterback.

$90 million down the drain.