The Chicago Bears are going to end the 2010s decade as one of the worst in franchise history. They’ll have made the playoffs a grand total of two times with one postseason victory to show for it. The only decade worse than that was the 1970s when they also made it twice but didn’t win a game either time. Not exactly the kind of company this organization wants to keep. Yet that is the state of things and people are only left to ask the question.

What in the world went wrong?

Often in these cases, it’s best to pinpoint their worst moves. Teams that don’t win much tend to have a lot of high profile busts, be they draft picks, free agent signings, or trade acquisitions. The Bears most certainly qualify in that regard. So which moves were the most directly responsible for this sustained trend of ineptitude? Here are the top 10.

Worst Chicago Bears moves of the 2010s

10. Pernell McPhee

It feels difficult to put a guy like McPhee on this list. He was a locker room leader and a tough football player who really helped kickstart the process of the Bears defense recovering from the nightmare of 2013 and 2014. That said, he never was able to reach his full potential in Chicago. This due to constant health problems. Most of them centering around his lower extremities that constantly made it difficult to play.

GM Ryan Pace handed him a 5-year contract worth $38.75 million. That kind of money sent a clear message that they expected him to be an anchor for their pass rush. What they got was 14 sacks in 36 games. Nothing close to what was hoped for. McPhee was gone after three seasons, having missed 10 games over the final two. He’s never been quite what he was before those injuries during stints in Washington and Baltimore since leaving.

9. Adam Shaheen

Normally a 2nd round pick doesn’t make lists like these but Adam Shaheen found a way to be an exception. The tight end out of Ashland came in with a ton of hype in 2017. Many likened him to Rob Gronkowski with his mix of size and athleticism. They dubbed him “Baby Gronk.” Expectations were he’d at least become a nice addition to the passing game the Bears were trying to build in their new offense. They would end up disappointed.

It was always something with Shaheen. Every time he seemed to be building a little momentum, he’d almost invariably get injured. This trend continued right into 2019 where a back injury stunted his season before it even began. Eventually, he landed on Injured Reserve with a foot issue, his Bears career likely coming to an end having managed 26 catches for 249 yards and four touchdowns in three seasons.

8. Jared Allen

GM Phil Emery took a calculated risk in 2014 when he chose to part ways with veteran pass rusher Julius Peppers despite him still having a year left on his deal. It was felt with his 34th birthday coming up that he was pretty much on the decline. Emery wasn’t concerned though. That March he pulled what many thought was a coup when he signed former Vikings superstar Jared Allen to a four-year deal for $32 million.

It seemed like an easy move at the time. Allen had posted 11.5 sacks the previous year and had shown no signs that he was losing a step. As the season began though, disaster struck when Allen came down with a bout of pneumonia. This caused him to drastically lose weight and he was never quite right again after that. He finished with just 5.5 sacks that year. Three games in 2015, he was traded to Carolina and would retire at season’s end.

7. Cody Parkey

Desperate for kicking help after Robbie Gould’s departure, the Bears decided to put their money where their mouths were in 2018. They handed $9 million in guaranteed money to veteran Cody Parkey to become what they thought would be their starter for years to come. On the surface, it seemed legit. Parkey had been a Pro Bowler in Philadelphia and had a bounceback year in 2017 for Miami, connecting on 21-of-23 field goals.

It didn’t take long to find out that the man was in no way prepared for the challenges he’d face in Chicago. Not only was he living in the shadow of Gould, the greatest kicker in franchise history, he also was not ready for the Soldier Field either. The stadium was notorious for giving kickers problems over the years and Parkey only made it worse on himself by choosing not to practice there during the week. He ended up missing 11 kicks that season, including the now-iconic Double Doink in the playoff loss to Philadelphia. He was gone by January.

6. Mike Glennon

With Jay Cutler finally out, Pace was free to reshape the quarterback position as he saw fit. Most expected him to use his top 5 draft choice for that mission, which he eventually would. That only ended up making his decision to hand $15 million a year over three seasons to veteran Mike Glennon. The former 3rd round pick had spent most of his career in Tampa Bay as a backup. The Bears’ initial plan was for him to be the starter for 2017, allowing their young draft choice time to sit and learn.

Instead it ended up creating a major controversy. On top of that, Glennon became a disaster in the space of just one month. The Bears went 1-3 and the quarterback was a big reason for their issues with turnover problems. This forced the coaching staff to make a change. All told? The team had guaranteed Glennon a grand total of $18.5 million for four games of work. That is some of the worst money the organization has ever spent.

5. Gabe Carimi

The Bears offensive line was a mess in 2010, allowing 56 sacks during the regular season. It was plain to all that the unit was in desperate need of retooling. GM Jerry Angelo figured the best place as any to start was the draft. However, by 2011 somebody should’ve warned him off from that. For all the good things Angelo had done in his tenure, drafting reliable offensive linemen was not one of them. His two previous 1st rounders in that area (Marc Columbo and Chris Williams) were disappointments.

Still, the Bears forged ahead, selecting standout tackle Gabe Carimi 29th overall. It seemed like such an easy pick. Wisconsin was a factory for good offensive linemen and Carimi was a big, strong, and tough blocker who fit what the team wanted to do offensively. Then in his second career game? He dislocated his kneecap. This led to serious complications that the tackle never fully recovered from. He was traded after just two years and was out of the league by 2015. A setback that ultimately contributed to Angelo being fired.

4. Mitch Trubisky

A lot of people might be shocked this isn’t higher. Trubisky was the #2 overall pick in the 2017 draft. Not only that. The Bears traded three more picks to move up and get him. At the same time, they passed on two other quarterbacks named Patrick Mahomes and Deshaun Watson. Both of whom have gone on to become established stars in Kansas City and Houston. It offers a gut-wrenching reminder of how inept the Bears have been at identifying great quarterbacks for the past several decades.

So why only #4? Largely because one can’t call Trubisky a complete bust. Sure he hasn’t lived up to the standard that Mahomes and Watson have set, but he’s been productive at times during his young career. His 2018 season was one of the best a Bears quarterback has had in the Super Bowl era and became a catalyst for the team breaking one of their longest playoff droughts. It’s a small consolation prize, but it’s enough to keep him out of the top 3.

3. Greg Olsen trade

It remains mind-boggling to this day on what the Bears were thinking. Another reminder that obsession with schemes in the NFL can often lead to appalling personnel decisions. For the Bears, it’s never gotten worse than this. They drafted Greg Olsen in 2007 as part of a new wave of tight ends sweeping the league. Guys who were not only big but athletic and fast, capable of gashing defenses down the field.

Olsen came into his own in 2009, posting 612 yards with eight touchdowns. The arrival of Mike Martz the next year though changed everything. Olsen had only 404 yards that season but still tied for the team lead with five touchdowns. He was instrumental to the Bears’ playoff victory over Seattle as well. Did this matter? Not a bit. When the 2011 offseason arrived, the team casually shipped him off to Carolina for a 3rd round pick. Olsen has 522 catches for 6,451 yards and 39 touchdowns since leaving.

2. Kevin White

Sometimes it isn’t necessarily bad decision-making that leads to these kinds of moves. Bad luck can play just as big of a part. Several experts agreed that West Virginia standout Kevin White has sky high potential for the NFL. A 6’3 monster with 4.35 speed. Once he learned how to master route running, there was nobody on the planet who could stop him. What nobody could account for was the injuries.

White was snakebitten from the very beginning. He broke his leg before even stepping foot on the practice field his rookie season. Then in 2016, he broke the other one after just five games. In 2017, things got even weirder when he broke his shoulder blade in the season opener. By the time 2018 rolled around, the team had run out of patience. White barely played and was released after the season ended. All told, the Bears got 285 yards in four years out of a 7th overall pick.

1. Shea McClellin

Some people might consider this a bit of an upset considering McClellin was only the 19th pick overall vs. where White and Trubisky were taken. However, context is always key. McClellin was a slight unknown throughout most of the draft process in 2012. He only started to gain traction after the scouting combine when he performed well during the drills, showcasing his athleticism and versatility. The Bears were in the market for a young pass rusher what with Julius Peppers pushing into his 30s.

Unfortunately, GM Phil Emery showcased his appalling lack of preparation when he chose McClellin. This with far more proven options on the board. None more so than Chandler Jones out of Syracuse. He has since gone on to post 96 sacks in his career. Whitney Mercilus, out of the Bears’ own backyard at Illinois, went 26th and now has 50 sacks. McClellin retired with 8.5. That pick set the tone for Emery’s entire tenure and began the Bears on a downward spiral to becoming one of the worst teams in the NFL four years later.