Here are the five biggest mistakes made by the Chicago Bears franchise in the last five years (2011-2016). It is very hard to limit this list to five, and some will surely disagree on which ones were the absolute worst, so feel free to vote on your favorite disastrous decision at the end.
#5. Trading Greg Olsen To The Panthers - 2011
In July of 2011, the Chicago Bears traded tight end Greg Olsen to the Carolina Panthers in exchange for a third-round pick in the 2012 NFL Draft. Olsen had just finished his fourth season with the Bears which was a slight decline from his 2009 campaign where he scored eight touchdowns. In his previous three years with Chicago, before getting traded, Olsen scored 18 total touchdowns. His receptions peaked at 60 in 2009, but it was obvious to everyone he had unique scoring ability. Olsen went on to appear in three Pro Bowls for Carolina and he's played five, full, 16-game seasons in a row. He's also been considered a top TE in the league for the last few years. Chicago never selected with Carolina's third-round pick, instead they traded it to Miami as part of the deal for Brandon Marshall. That turned out to be quite the mistake considering Russell Wilson was still on the board during that pick. The Bears went on to draft Brandon Hardin with their own third-rounder that year and he never once appeared in a real game due to various injuries. Marshall only stayed with the team for three seasons and caused a lot of damage in the locker room each day he was here. The Bears are still indirectly recovering from the decision to trade Olsen back in 2011.#4. No Competition For Jay Cutler - 2009 - Present
Spoiler, trading for Cutler is not on this list. The first reason is because it was in 2009 and the second reason is because that wasn't a terrible decision when it was done. Cutler was a starting quarterback that became available in a very unique situation allowing the Bears to capitalize and fill a need. One of the biggest mistakes Chicago has made though, since originally acquiring Cutler, is not bringing in real competition for him. Instead, the Bears rotated coaches trying to fix a problem that inevitably will never be fixed, Cutler's decision making. Think about it. The first names that likely come to mind when you think about capable Cutler backups are Josh McCown and Caleb Hanie. We used the word "capable" loosely there. Both of those quarterbacks were signed to hold the clipboard and both of them, after getting a chance to play, caused a quarterback controversy in Chicago. The reasons wasn't because either of them were spectacular in any way, it was because the team didn't show a huge drop-off when Cutler wasn't playing. Many will disagree on the talent levels that separate Cutler from McCown and especially Hanie, but when you look back on it now it appears "fixing" Cutler was a lost cause. To try and boost Cutler's confidence level, and essentially keep him happy, Chicago never really signed a capable quarterback that would actually compete with him to start. They also never really drafted one, none of the Bears' picks since Cutler arrived were used on a quarterback higher than the fifth round. The reason is likely because the Bears saw a path of success with Jay, unfortunately it never came to fruition. If the Bears would've focused more on bringing in competition for Cutler, they would have more of a success plan than they do now which is likely to result in #6 getting cut. Too bad we can't tap David Fales to come and start next year .... and that's because he was taken in the sixth f-ing round.#3. Firing Lovie Smith - 2013
Listen, we all know Lovie Smith is one of the most boring humans on the planet. His media conferences will put you to sleep and his indirect way of answering questions will annoy the hell out of you. But the fact of the matter is .... he was winning in Chicago and build a unique culture here. Smith was essentially fired after going 29-19 in his final three seasons. The Bears appeared in a 2006 Super Bowl, and won the NFC, once during his tenure. He was 10-6 in his final season, but missed the playoffs.... so the Bears canned him. Most Chicago fans know that really wasn't the reason Smith was fired though, he was fired because he wasn't able to fix the Bears' historic quarterback problem. Thinking Cutler was the answer, and Smith wasn't, management decided to go in another direction. Shortly after that, Brian Urlacher and Lance Briggs basically hung them up. Urlacher retired and Briggs played two more mediocre seasons where his commitment level was questioned several times. The defensive mentality Chicago built, under Smith, was completely gone the following season when the Bears tumbled to the 30th ranked defense. That was after they finished 5th in Smith's final year. Had the Bears kept Smith, and got rid of Cutler, things may look quite different in Chicago.#2. The Hiring Of Phil Emery (and Marc Trestman) - 2012
Holy hell, sorry to bring you back into this nightmare Bears fans. The only positive names associated with Phil Emery are Alshon Jeffery and Kyle Long. Outside of that, most of his time in Chicago could be classified as a trainwreck, including the hiring of Marc Trestman. Bringing 14 years of experience and previously spending three years in Kansas City, the Bears chose Emery to become the teams fifth general manager. He was loosely connected to drafting Urlacher and Briggs when working as an area scout for the team back in 1998-2004. He replaced Jerry Angelo and hired Trestman to be his coach after firing Smith just a year into the job. Trestman lasted just two years after going 13-19, then him and Emery were fired. The name Shea McClellin is popular in Chicago because he was Emery's first draft pick and he sucked. Emery was also responsible for the Marshall trade and the selection of Hardin which both turned out to be bad decisions. Two of Emery's three first round picks are huge busts (McClellin and Fuller), his third was Kyle Long. Current general manager Ryan Pace is still trying to clear the roster of failed players from the Emery era. Most of the players he drafted aren't even on the roster anymore and a good portion of the rest will go this off-season. Emery can also be linked to not bringing in competition for Cutler (#4 on this list) and our #1 choice for the absolute worst decision by the Chicago Bears franchise in the last five years ....#1. The Jay Cutler Contract Extension - 2014
This might be the most frustrating decision, from a fan's perspective, in the history of the franchise. Cutler signed a seven-year $126.7 million contract extension back in 2014 worth $54 million guaranteed. They did this just after Cutler and the Bears finished 8-8 in their first season under Trestman. Since that decision, the Bears have finished in fourth place in their division three years in a row. Each of those seasons Cutler was ranked as one of the highest paid quarterbacks in the league and the Bears had 12 total wins with him at quarterback, they also had 33 losses. The team wasn't the only thing that was bad though. The first year after signing the extension Cutler tossed 18 interceptions, his highest season total going back five years. Had it not been for the one good season Cutler had under Adam Gase in 2015, this could arguably be the worst decision the franchise has ever made. The main reason it was SO bad was because they could've just franchised him. The Bears had the ability to use their franchise tag and let Cutler earn his money, like most players do. Instead, they gambled on improving Cutler's happiness, which is next to impossible given his public persona, and gave him $54 million and seven years. Here we now sit, three short years later, and he's likely going to be cut which is going to void off the four final years of the contract.... more than half of it. Thanks to Phil Emery and the McCaskey family.VOTE:
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