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Jay Cutler never had a chance in Chicago. He leaves behind an unfulfilled legacy of lessons

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Cutler was set up to fail in Chicago, and everyone involved with the Bears was at fault - including him. The team would do well to learn from these dire mistakes.

NFL: Detroit Lions at Chicago Bears Mike DiNovo-USA TODAY Sports

On April 2nd, 2009, the Chicago Bears traded for the star-crossed former Denver Broncos quarterback in Jay Cutler. The recent news of Cutler’s 2016 season ending due to a torn labrum places perspective on an era that may be coming to an end. Chicago can cut Cutler after the season for minimal costs as he has almost no guaranteed money left on his deal. It brings to mind a time that could’ve and should’ve been more vibrant.

Cutler’s arrival promised stability and hope for a franchise who had never enjoyed a quarterback with his talents. While his acquisition came at a high price - two first round picks, a third rounder, and Kyle Orton - everyone involved was pleased with the bounty. It’s never that simple in the NFL, but a true franchise quarterback was supposed to make all concerns across the rest of the roster dissipate. At least according to former general manager Jerry Angelo.

The common underlying consensus was that Cutler would dazzle Soldier Field crowds for years to come. It’s difficult to believe in hindsight now, but there was once a prevailing thought that Cutler was every bit Green Bay Packers superstar, Aaron Rodgers’ equal. He was supposed to build a rivalry with the now future Hall of Famer as both would have their teams dueling for the top of the NFC North and conference supremacy for a decade.

Obviously, for many reasons these sentiments never came fully to fruition.


Cutler’s failures in 2009 seemed misguided in retrospect. Yes, the Bears missed the playoffs with a 7-9 record, but Cutler’s struggles with 27 touchdowns to 26 interceptions, were of minute concern. Never mind his less than inspiring debut to his “rival” Rodgers where he threw four interceptions on ‘Sunday Night Football’ in Lambeau Field: a place that would become Cutler’s house of horrors. That season was supposed to be an aberration. Angelo’s plan of inserting a quarterback into what became a bare bones offense sans Matt Forte was the ideal. The general manager manager never worried, even as obstacles eventually dragged him from his Halas Hall perch.

"We felt that [Cutler] is a very good person, a good leader," Angelo said in his initial reaction to acquiring Cutler.

These results were only year one.

Chicago was considered to be on the rise. They had stalwart defensive superstars such as Brian Urlacher, Lance Briggs, and Charles Tillman. With Julius Peppers’ addition in free agency the following 2010 off-season, the Bears were a budding dynamo. Never mind the firing of offensive coordinator Ron Turner to mitigate all consistency - another common theme of the Cutler Bears era. Chicago had it’s plan. While Cutler didn’t exactly light it up in 2010, he was more consistent in helping lead the team to it’s first NFC Championship Game berth since 2006.

The beginning of a quality three-year run that had most grasping for answers at conclusion.


Chris Williams, Gabe Carimi, J’Marcus Webb, Frank Omiyale, Lance Louis, Orlando Pace, Chris Spencer, Jonathan Scott, Jordan Mills, Eben Britton.

These are some of the names that have rotated throughout Cutler’s protection up front in his Bears career. Most of these linemen aren’t in the NFL anymore. Save for men like the always reliable Olin Kreutz and Kyle Long, there was never much stability, or even talent on Chicago’s offensive line. This led to Cutler being sacked 184 times over his first four seasons with the Bears: an average of 46 times a year.

Devin Hester, Devin Aromashodu, Roy Williams, Johnny Knox, Rashied Davis, Juaquin Iglesias, Eric Weems.

These are some of the names Cutler had to work with in throwing the ball down the field before enjoying Brandon Marshall and Alshon Jeffery among others. Save for Knox, who had a career ending back injury in 2011, there wasn’t much here. Cutler worked with a kick returner being shoehorned into a receiver in Hester, a flash-in-the-pan in Aromashodu, a shell of his former self in Roy Williams, and other players qualified as less than able NFL options.

The trade of tight end Greg Olsen in 2011 looks less satisfactory by the day.

Of course, a rotating stable of offensive coordinators didn’t help.

From the formerly mentioned Turner, the past-his-time Mike Martz, an inexperienced and out of his wits, Mike Tice, a man who eventually attempted to lead a mutiny against his own quarterback in Aaron Kromer, to the best of the bunch in Adam Gase: Cutler never enjoyed the luxury of consistent offensive systems. This includes the present man, Dowell Loggains.

No quarterback could survive under that consistent attrition, yet Cutler and somehow the Bears, for whatever reason pressed on.


Three head coaches. Six offensive coordinators. A 51-51 record in 102 starts with only one playoff appearance in eight years.

Cutler’s body broke down more often than the Bears would’ve liked, as he played a 16-game season just once in Chicago, in 2009. A plethora of lost potential at the offensive skill positions along with overall mismanagement and lack of development. A shaken image of a lack of toughness or leadership all because he left a playoff game due to a serious injury, even as his teammates and coaches continually praised him grinding out through injuries. Loggains did the same after the most recent Cutler news.

“Jay (Cutler) would do anything to be out there playing”, said Loggains of Cutler on Thursday. Try as those on the outside might, those within the organization always knew what Cutler gave to this team.

Quibbles over his contract extension in 2014 that many assumed made him overpaid instead of adequately rewarded for his services by the time others like Joe Flacco and Andrew Luck received extensions, were misplaced. A quarterback like Cutler - who never seemed to shake his inability to make the simplest of plays every other great passer made routine - didn’t help himself either.

Many aspects contributed to Cutler’s lack of success and everyone’s to blame.


There were opportunities in 2010, even as the Bears fell to the Packers with a chance at a Super Bowl, or in 2011 when Cutler injured his thumb while trying to make a tackle late in a victory over the San Diego Chargers. These early Cutler teams were the best chance at an opportunity for a championship and were emblematic of misplaced faith through the rest of his tenure in small flashes.

This led to the debate among fans and no doubt the organization alike. “How will the Bears ever do better?” or “How could they move on from him without a plan?”

The Bears and everyone that concerned themselves with the results of this team threw themselves for a loop over Cutler. He was always the center of conversation even if he wasn’t the Bears’ primary problem on the roster. Cutler was over-scrutinized, over-diagnosed and seen as a man who was the key to Chicago’s success. He could never inherently never live up to the city’s expectations. Such is the plight of a starting Chicago quarterback until the end of time.

Win a Super Bowl in Chicago, and you’re untouchable. You’ll never have to buy your own dinner while in the city again. Build up unattainable expectations through no fault of your own and don’t meet them and you’ll become a pariah as frustrations continually grow. Cutler could never win in Chicago unless he did the former.

If Cutler has indeed played his last game with the Bears, he will retire with almost every relevant passing record. Sure, a Bears passing record means as much now as a Chicago Cubs' playoff win before 2015, but you can’t discount the success he did have to attain these results. He was a step in the right direction for this franchise in the modern era. It just wasn’t the gigantic leap initially assumed. That should be commended alone.

Moving forward, the Bears would do well to learn from their mistakes with Cutler, and place whomever the next likely quarterback is in an immediate position to succeed. They need the next face of the franchise to have proper support. This is a team game, and Chicago would do well not to forget that fact. Unlike Cutler, this young man will need to be given a chance immediately. Cutler’s legacy as Chicago’s best quarterback ever - at least statistically - offers that lesson.

This was a modern day football tragedy told in surly Cutler faces. While it didn’t end how many had hoped, the misunderstood and complicated legacy of Cutler will live on in Bears' lore, for better or worse.

Robert Zeglinski is the Bears beat writer for The Rock River Times and is an editor for Windy City Gridiron. You can follow him on Twitter @RobertZeglinski.