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30 Day Challenge: Which Bears player never had a fair chance?

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Every day in the month of June, we'll ask a different Chicago Bears-related question to our readers. Make sure you guys participate the entire month, so we can all get to know the WCG community a little better. Today, we dig into which Bears player never got a fair chance.

NFL: Chicago Bears at New York Giants
The odds were against Jay Cutler to succeed throughout his tenure with the Chicago Bears.
Brad Penner-USA TODAY Sports

Please don't kill me for this one.

There have been a myriad of blockbuster trades and signings in the NFL's past. A lot of them start because of the same situation: a team is just one big move away from being a playoff contender, so they put all of their marbles in one jar and add a star-caliber player. Sometimes, these moves pay off. Other times, however, they do anything but.

The Chicago Bears were fresh off of a 9-7 season in 2008. They ended up finishing one game out of first in the NFC North, and only one-half of a game out of a wild card spot. While a handful of factors attributed to their falling short, one of the biggest ones was their mediocre quarterback play. Then-starter Kyle Orton finished 19th in the league in passing yards, 13th in touchdowns, and 25th in completion percentage and QB rating. Although there were a handful of teams in worse situations, it was clear that the Bears wouldn't be able to become a true contender with Orton as their signal-caller.

Then, out of the blue, like an angel descending from the Heavens, Jay Cutler became available on the trade market.

Cutler was just coming off of the best season of his young career. He finished third in passing yards and seventh in touchdowns en route to his first Pro Bowl appearance. At 25 years old, he appeared to be the face of the Denver Broncos for years to come. That is, of course, until Josh McDaniels arrived.

After McDaniels became the team's new head coach, rumors emerged that the Broncos were open to trade offers for the quarterback. Needless to say, Cutler wasn’t happy about that. He felt insulted, sold his Colorado home and requested a trade. Many teams were interested in the Vanderbilt alum's services, but the Bears eventually won the Jay Cutler sweepstakes. It took them two first-round picks, a third-round pick and Kyle Orton to do so, but in the minds of many, it didn't matter: the Chicago Bears finally had a franchise quarterback.

Cutler’s big arm, athleticism and toughness had Bears fans everywhere excited for the future of the franchise. However, some nine years later, it’s now apparent that he was never given a proper chance to succeed.

Cutler’s first season as a Chicago Bear didn’t necessarily end up like fans had hoped. He failed to repeat his successes of the previous year, and threw a league-high 26 interceptions. In fact, Kyle Orton, whom the Bears traded to get Cutler, had a better season than their new quarterback. That season doomed his run from the start.

For starters, Chicago’s offensive weapons were anything but ideal. Sure, they had Matt Forte in the backfield and Greg Olsen at tight end, but their group of wide receivers was arguably the worst in the league. Their No. 1 wide out was Devin Hester, who, as some may recall, wasn't even a natural wide receiver to begin with. Their other options included Earl Bennett, rookie Johnny Knox and Devin Aromashodu (remember him?). To put things into perspective, Cutler had Brandon Marshall and pre-injury prone Eddie Royal to throw to in Denver. Both of those wide outs topped 90 receptions and 950 yards in 2008, whereas only Olsen topped 60 receptions in 2009.

Speaking of Olsen, the Bears decided to limit his receptions after they brought in Mike Martz as their offensive coordinator. It was bad enough that they changed offensive coordinators one year into Cutler's tenure, but that change greatly hindered their most talented offensive weapon. The Bears were able to ride to the NFC Championship in 2011 off of the coattails of their defense, but their offensive firepower was still lacking.

Olsen was traded in 2010 because he didn't fit Martz's scheme. Martz was gone after the 2011 season, while Olsen went on to become one of the best tight ends of the 2010's with the Carolina Panthers.

It wasn't until Cutler's fourth year with the team that the Bears truly decided to improve the wide receiver position. In 2012, they traded for his top wide out in Denver, Brandon Marshall, and drafted Alshon Jeffery in the second round. At last, things were looking up for the Bears. Although they finished just short of the playoffs, they had a 10-6 record and could seemingly only improve from there.

Then Marc Trestman came to town.

The Bears had fired general manager Jerry Angelo after the 2011 season and replaced him with Phil Emery. Emery, who wanted to mold the team in his image, called for a facelift to the staff that wasn't really needed. Chicago fired long-time head coach Lovie Smith, as well as offensive coordinator Mike Tice. They also drove out defensive coordinator Rod Marinelli, who was (and still is) one of the best at his job in the NFL. Emery replaced those three coaches with CFL standout Marc Trestman, Aaron Kromer and Mel Tucker, respectively.

The turnaround in philosophy was apparent from the get go. The Bears had finished 16th in points scored and third in points allowed in 2012. One year later, they finished second and 30th in those respective categories. While Cutler finally had a system in which he could flourish and talented players around him, the defense suffered greatly as a result. What had been one of the league's best defenses year in and year out was now one of the biggest jokes in the NFL. It would've been a challenge for any quarterback to lead a competitive team with that defense, let alone Cutler.

The following year, the Trestman magic wore off. Chicago fell from 8-8 to 5-11, their offense collapsed, and their defense remained abysmal. The locker room was a nightmare, and the play on the field was just as bad. Trestman and Emery were both fired after the 2014 season. Marshall and tight end Martellus Bennett were both traded when the Bears hired Ryan Pace as their new general manager, and Forte was gone the following year.

At that point, Bears fans had given up on the idea of Jay Cutler as their franchise quarterback for years. Despite flashes of potential, he had never proven that he was capable of leading a Super Bowl-caliber team. Things got to the point when people considered Josh McCown, a journeyman backup who had performed well in his absence in 2013, to be a better option at quarterback than Cutler.

The 2015 season was a slight bounce-back season for Smokin' Jay. He had a career high in QB rating, the lowest amount of interceptions thrown since his 10-game 2011 season, and an above-average completion percentage. Under offensive coordinator Adam Gase, Cutler almost seemed like a new quarterback. However, Gase left to become the head coach of the Miami Dolphins after that year.

That brings us to the end of the road for Jay Cutler. He only played in five games last year due to injury, and was released at the end of the season, hence bringing an end to his underwhelming nine-season tenure in Chicago.

Did Cutler himself have anything to do with his disappointing run with the Bears? Absolutely. Turnovers and bad decision making plagued him throughout his time in the Windy City. Plus, Cutler only played all 16 games in one season with the Bears: his first season. He missed 26 games in total due to injury.

Those factors certainly played a big part in Cutler's lackluster performance with Chicago. However, it wasn't entirely his fault.

Cutler had six offensive coordinators and three head coaches with the Bears. For the first half of his tenure, he was throwing to players who would've been No. 3 receivers at best on most teams. His offensive line was bad for a long time, as well. Cutty finished in the top 10 in times sacked four times with the Bears, reaching the top spot once.

And once he actually had help in those areas, other factors prevented him from leading the Bears to the playoffs. Whether it be poor defense, awful coaching, locker room unrest or all three, Cutler never had a chance to work with playoff-caliber talent.

Cutler had his fair share of mistakes, there’s no doubt about it. But maybe, just maybe, we as Bears fans tend to forget that he was almost doomed to fail from the start.

Now it’s your turn. Which Bears player didn't have a fair chance to succeed? Let us know in the comments below.