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Was the Jay Cutler acquisition a mistake? Six questions about #6 (part 2 of 2)

When it’s all said and done, what will you remember FIRST about Jay Cutler? The WCG staff answers that question and five others in Part 2 of “Six questions about #6.”

Divisional Playoffs - Seattle Seahawks v Chicago Bears Photo by Andy Lyons/Getty Images

In Part 1 of our “Six questions about #6,” we asked if Jay should be back next year, the single biggest factor that led to the Bears not winning a Super Bowl during his tenure, and the Cutler season that represents the biggest missed opportunity.

(Our dominant responses: Probably not; crappy personnel moves; 2011.)

In Part 2, we explore our collective Cutler memories, and bask in many a YouTube clip.

4. When it's all said and done, what will you remember FIRST about Cutler's time in Chicago?

4 votes: Hope

Sam Householder, @samhouseholder: I'll never forget that feeling of excitement and hope that came when the Bears traded for the former Denver QB. The excitement of having a bona fide live-arm QB for the first time in my life.

His toughness, especially in the face of adversity and injury, is a close second.

Steven Schweickert, @SJS_Illini: The hope that the Bears may have gotten that top-level quarterback, followed closely by the failures to actualize that potential.

Robert Zeglinski, @robertzeglinski: That initial feeling of unrelenting hope — that finally, the Bears had a legitimate star quarterback. For the first time, this franchise had bought itself quarterback stability, even if at a high price of draft picks.

I thought it was inevitable that Chicago was on track for multiple championships, but the best laid plans of mice and men often go awry. The theme of missing potential hung around Cutler's entire tenure with the Bears.

Ed Snyder: The flashes — of promise, talent, athletic ability, ‘wow’ plays — and that they never happened consistently enough for the team to win regularly. That's the most frustrating thing about all of it. It's not that he couldn't do it, it's that he never did it consistently enough to stack up performances that we knew he was capable of.

Houston Texans v Chicago Bears

Other answers

Jack M Silverstein, @readjack: I hate to say it, but the 2010 NFC championship game. I don't blame Jay for leaving that game; he did, after all, have a torn MCL. But our defense gave Aaron Rodgers the business -- his 55.4 rating is his lowest ever in the playoffs -- and we nearly sent the game to overtime with Caleb Hanie.

It's not fair, I guess, but that game is what I'll think of first.

Jeff Berckes: The arm talent. I love watching him sling it. Some of his throws are unbelievable — if any of us had that arm, we too would believe we could make any and every throw.

Josh Sunderbruch: His unflagging support for team and organization. He makes throws that seem superhuman but guys drop the ball? He says he needs to do better to give his receivers a change. His offensive line lets him get sacked into the ground? He says he has to take better care of the football. Lowlife punk tattles on him to the media on the way to starting a fight about chairs? Jay talks about how it's all better now.

The guy organizes his teammates every off-season. It sticks out because he is actually the opposite of what people seem to thing he is.

Ken Mitchell, @WCGBearsDenDude: Spongie's head exploding.

Lester Wiltfong, @WiltfongJr: I know Cutler was always knocked because his demeanor, but I always found it refreshing that he didn't give the same tired, canned responses. Cutler wore his emotions on his sleeve and I was OK with that.

5. Okay, okay, we've heard all the negatives. What is your favorite memory of Jay Cutler, Chicago Bears Quarterback?

Silverstein: His passing abilities! That sounds basic, but nothing about the Bears quarterbacking in my life prior to Cutler even reached "basic." When we traded for him, I was in awe of things like "his arm" and "his height". He made passes the likes of which we've never seen in Chicago.

My favorite was probably the 56-yarder to Brandon Marshall that led to a game-tying field goal against Seattle in 2012. No other Bears QB could have made that play.

Berckes: If I had to pinpoint a throw, it would be that long TD up the seam to Greg Olsen in the 2010 playoffs against Seattle. I thought, Wow, that's going to be an amazing combination for years to come. I really enjoyed the 2010-2012 ride with this team and Jay was a big part of that.

Sunderbruch: It shouldn't be, but him trucking Robert Golden is #1.

Mitchell: Thanksgiving, 2015. Somebody, please insert the "Rodgers throwing helmet" GIF in the comments for me. Just try not to hurl if you listen to the announcers as they fawn over the LOSING quarterback.

Householder: Wow, that’s tough. I think No. 1 for me will be the Monday Night Football upset over the Vikings in 2009, when Cutler threw the winning TD in overtime to Devin Aromashodu. It was a fun game and very personal to me because I was there in person with my now-wife, and it was her first game. That will always be a special memory.

I also remember his helicopter rush TD over the Lions and the 2011 MNF loss to the Lions where Cutler was fighting off a vicious Detroit pass rush and throwing to Dane Sanzenbacher, Devin Hester and Sam Hurd. But overall, just the awesome throws he could pull off — the TD to Marquess Wilson against the Chiefs last year, Alshon Jeffery's first career TD, the game-winner to Zach Miller against the Chargers, and on and on.

Schweickert: The overtime throw to Devin Aromashodu to beat the Vikings. The "A Bears quarterback made THAT throw to win the game" feeling.

Wiltfong: I don't really have a favorite, but Cutler did have 18 game-winning drives during his Bears career.

Snyder: The passing displays. His arm is crazy-good and he owns the majority of Bears passing records for a reason. He can sling it. Watching him toss lazers on the run off a rollout is fun, it really is.

Zeglinski: I know people want to forget the 2014 season overall, but Cutler's gutty performance against San Francisco on Sunday Night Football will always resonate with me. Four touchdowns and leading his team after getting beat up in a gutty comeback was just vintage Cutler. If only that win was as big as we initially thought.

I’ll also always think of his general surly honesty with the media. We often made jokes about it, but Cutler really didn't care what anyone thought of him, outside of people in the Bears organization. That was refreshing.

6. Knowing what you know now, if you could go back to April 2, 2009, would you still trade for Cutler?

Berckes: Absolutely! In an alternate universe, Jay Cutler has 2 Super Bowl rings, he can't pay for a drink in Chicago, and people are talking about how he's on the bubble for a Hall of Fame career like Eli Manning. It was an aggressive move that brought in arm talent like we've never seen in Chicago before. It didn't work out but that doesn't mean it wasn't the right move at the time.

Sunderbruch: If I get to move forward from that moment, then yes. Even slightly better drafting, offensive consistency, or luck makes the Cutler version of the Bears into contenders. If you're just asking me if I'd like to repeat 2009 to 2016 again with no changes and all of the heartbreak, then no thank you. But that's not on the Cutler trade. A lot of decisions went into the disappointment.

Zeglinski: I'd still make the trade. Throughout Cutler's entire Chicago career, he masked this offense's deficiencies while making mistakes of his own. This is the quarterback he's always been from high school to college to the pros — trying too hard to cover for everyone else.

Travel back and tell Jerry Angelo to get some offensive linemen and a receiver or two. I shudder at the thought of where the Bears would have been without Cutler, but maybe they would have bottomed out sooner and acquired a true franchise quarterback at the top of the draft.

Hopefully we’ll properly plan around the next quarterback and learn from the mistakes surrounding Cutler. Regardless, I find myself regretting nothing about the last eight years.

Schweickert: Here's the thing: You have a chance to acquire a young quarterback coming off his first Pro Bowl appearance with a ton of arm strength and good mobility. Your current guy is all right, may not be anything special, but is solid enough. The price is steep, but if you hit right and you can add pieces around him, you've got a top tier quarterback. At the time, it's certainly a viable move and, if the Bears win in Green Bay and go to the Super Bowl, are we even having this conversation?

There are so many points where things hinge since the trade that make this really hard to answer, especially early in his tenure. Stick with Lovie? Hire Ballard instead of Emery?

If the choice is this exact end point or no trade at all, then it's probably "don't make the trade." But if even one of those hinge points changes, this is a very different topic. Any regrets about the trade though? Nope. Too late to play that game. The Bears got a young quarterback at a young quarterback price with some decent W-L results between 2010 and 2012.

Householder: I would. I know it didn't work out, I know it's divided a lot of fans, but Cutler has gotten an unfair rap and I think it easily could have been so much worse. I honestly don't see how there would have been drastically different results with who they would have had instead of Cutler.

Wiltfong: Nope. I actually wrote an article before they made the trade about how I thought Kyle Orton was about to make a jump in play and lead the Bears to the playoffs. If you remember in 2008, the Bears nearly made the postseason, but a week 17 loss knocked them out.

Mitchell: No. If I were the McCaskey family and I knew what I know now, I would have fired Jerry Angelo and found a GM who could actually draft offensive talent.

Snyder: With hindsight, no. The price was high and it has not paid appropriate dividends. At the time, without the gift of knowing how it was going to work out? I probably would have made the move. It was the best possible option available to a team that was desperate for legitimate talent at the all-important QB position.

I hoped the Cutler experiment would work and there have been multiple times I thought it might. But being honest and looking back, it just has not panned out for either Cutler or the Bears. His overall record might sum it up best. Jay has won 51 games in Chicago, and lost 51 games. If you add in his 17-20 record with Denver, his lifetime professional record is 3 games below .500.

Silverstein: I could be a real bastard and say no, only because I can say in retrospect exactly what would have been better: roll with Kyle Orton in 2009, draft Clay Matthews with our abandoned 2009 first round pick, draft Mike Wallace in the third round, and then land our QB of the future in 2011 with Andy Dalton.

But that's not fair to Bears management; you can say something similar every year in every sport. I'm glad we took the shot on Jay. No matter what else, it’s been a fun ride.