Five Worst Trades in Chicago Bears History

Oct 5, 2014; Charlotte, NC, USA; Carolina Panthers tight end Greg Olsen (88) reacts after catching the winning touchdown in the 4th quarter. The Panthers defeated the Bears 31-24 at Bank of America Stadium. Mandatory Credit: Bob Donnan-USA TODAY Sports
Oct 5, 2014; Charlotte, NC, USA; Carolina Panthers tight end Greg Olsen (88) reacts after catching the winning touchdown in the 4th quarter. The Panthers defeated the Bears 31-24 at Bank of America Stadium. Mandatory Credit: Bob Donnan-USA TODAY Sports /
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1. 1967- The Chicago Bears trade Mike Ditka to the Philadelphia Eagles for Jack Concannon and an undisclosed draft pick

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Without question, this was the worst decision the Bears franchise has ever made and it was all due to George Halas being one of the cheapest owners in the NFL.

Mike Ditka came to the Bears in 1961 and revolutionized the tight end position. Before Ditka, the tight end position was nothing more than a sixth offensive linemen used to block and occasionally catch a pass. The Bears realized that Ditka was a weapon on offense and used him as a receiving threat. Ditka became the blueprint to what tight ends could be and opened the doors for future hall of famers John Mackey and Charlie Sanders to be utilized similarly shortly thereafter.

Ditka went to 5 consecutive Pro Bowls and was also All-Pro from 1961 to 1965.  Ditka and Halas constantly argued over his contract, Ditka once famously saying that Halas “throws around nickels like manhole covers.”

Halas grew tired of Ditka’s contract demands and shipped him to Philadelphia in 1967 for QB Jack Concannon. It was a bad trade for both sides.

Ditka spend two years pouting in Philadelphia before they traded him to the Dallas Cowboys where Ditka, despite being in the twilight of his career, returned to being a productive tight end. From the Bears perspective, Concannon never amounted to anything at quarterback.

In fact, he, while splitting time with Bobby Douglass, helped lead the Bears to their worst season in franchise history going 1-13 in 1969. Concannon only led the Bears to one winning season (1967) but that was thanks to Gale Sayers and one of the best defenses in the league, and very little to do with Concannon. When he wasn’t handing off to Sayers, he was usually busy throwing interceptions.