1. Trading Jay Cutler to the Bears in 2009
There can be no other trade in this slot for the time being. The Denver Broncos trading away Jay Cutler in the 2009 offseason is still the dumbest trade in franchise history, and that obviously includes a list in which they traded a 2010 first-round pick for the 37th overall pick in the 2009 NFL Draft.
Josh McDaniels was a horrendous GM, for the most part. He made some decent draft picks in two years with the Broncos and brought on players like Brian Dawkins, but he was horrible. It's part of the reason why some consider him the worst head coach in franchise history, even over Nathaniel Hackett. The reality is, McDaniels was a better coach than Hackett, but he was a horrible leader and a horrible general manager. He embarrassed the franchise.
When McDaniels was hired in 2009, he had one job -- take a team that had been on the cusp for three straight seasons and push them over the top. The Broncos had a good offense, and offense was McDaniels' specialty. Jay Cutler had just made his first Pro Bowl in 2008, but McDaniels' first order of business in Denver was not to get Jay Cutler excited to work with him, it was to sit him down and verbally undress him, taking such an aggressive measure to start a conflict that Cutler would demand a trade.
Which McDaniels was seemingly happy to accommodate. McDaniels did the unthinkable and put Jay Cutler up for sale that offseason. I'm still shocked to this day that Pat Bowlen didn't step in, but Bowlen chose McDaniels over Cutler at the time, and that's the reality of things. McDaniels sent Cutler to the Chicago Bears for a really nice haul of picks, which included first-round picks in 2009 and 2010. It also included quarterback Kyle Orton coming back to Denver.
It was misery. Everyone was excited to see what McDaniels could do with the promising weapons Denver had on offense. He had obviously done tremendous work in New England with Tom Brady and company. Now you bring the NFL's next wunderkind offensive mind -- just like Mike Shanahan once was -- and give him a bunch of Pro Bowl "toys".
And he blew it. He royally blew it. Cutler didn't go on to have a Hall of Fame career or anything, but it's once again the principle of the matter. McDaniels traded away a franchise quarterback just to prove he was the man in charge of the operation. It was a dumb decision then, and it looks worse with every passing year. It will take a colossal failure from Russell Wilson to replace this as the worst trade gaffe in Denver Broncos history, at least in my eyes.