Sack to the Future: What's in Store for Jay Cutler?

After eight less than impressive seasons Jay Cutler's time in Chicago may be coming to an end. Thanks to some amazing advances in technology I’ve been able to travel forward in time to see how he fared after leaving the Bears. Before we go any further I must warn you, it’s not pretty.

End of 2016 – Start of 2017

After going down with a thumb injury Cutler never regained the starting job from Brian Hoyer. Hoyer didn’t fare much better, leading the Bears to a 5-11 record. But he did have one major advantage in the fact that he wasn’t named Jay Cutler. Smokin’ Jay is cut just 15 minutes after the Bears’ season ending loss to the Vikings. Rather than travel with the team, he decides to make his own way back to Chicago. To this day the contents of his locker are sitting in a trash bag behind the tackling dummies, waiting to be picked up.

As the 2017 season approaches Cutler is courted by just two teams - the Browns and Dolphins. The Jets considered offering him a deal until Matt Forte and Brandon Marshall began sending tweets about how they were suddenly feeling "banged up" and "too old for this sh*t". When Forte tweeted a picture of a pipe, slippers and a rocking chair, Mike Maccagnan promptly deleted the email he’d been typing to Cutler’s agent and offered Ryan Fitzpatrick a contract extension.

Wanting to create some much needed competition at quarterback, the Browns eventually sign Cutler to a two year deal with a team option for a third. In a short-sighted attempt to raise their national profile they volunteer to appear in the 2017 edition of Hard Knocks. RGIII and Cutler battle week in, week out for the starting spot. Eventually it’s the player who made the least amount of mistakes (RGIII) who is named as the starter.

Hard Knocks highlights:

Week 1 – Jay arrives at camp and immediately alienates his new teammates by sauntering around in sweat pants and saying things like "So that's as fast as you can run?" and "Just turn around and catch it. Geez."

Week 2 – Cutler is demoted to working with the number two’s, much to the chagrin of… the number two’s.

Week 3 – In an attempt to work a little magic, Cutler goes off the page in the huddle when he makes the decree "Two guys go five yards, two guys go ten yards. Doesn’t matter who, doesn’t matter where. Ready? BREAK!" The ensuing pick-six made ‘Highlight of the Night’ on over a dozen regional sportscasts.

Week 4 – Cutler is spotted sitting on the bench during the national anthem, not because he’s protesting or anything, but because he was hunched over trying to light a cigarette. Battling the elements he eventually gets it lit and is on his feet just in time for "Gave proof through the night".

In limited preseason action Cutler finishes 11/31, for 106 yards, 0 TD’s and 3 INT’s. He did scramble away from a few rushers during a broken play in his final series only to throw one of his signature rockets through the back of the endzone. The injured cameraman agreed not to sue.

After securing the starting job, RGIII has an uncharacteristically good season, leading the team to a 10-6 record. Cutler grows a huge beard just for something to do.


In an effort to unwind Cutler spends the offseason in New Zealand. He, Kristin and the Cutlets enjoy the many outdoor pursuits that ‘Aotearoa’ has to offer. There’s no shortage of awkward looks as he strolls around Auckland saying "G’day mate!" to everyone he meets. The lowlight of the trip is when he asks a local shopkeeper if "that Crocodile Dundee dude ever hangs out around here?"

Cutler returns in time for camp having shaved his beard into a huge, thick moustache. The antics continue as he expertly keeps a straight face (as if he's ever made any other face?) while making comments like "I’m kind of a big deal" and "People know me". He starts every week by seeing how many times he can say the word ‘meow’ during team meetings. He’s released at the end of the season.


Cutty receives little interest during the offseason, from NFL teams anyway. The suitors he does have include the Montreal Alouettes (who are again being coached by The Quarterback Whisperer, Marc Trestman), the Arizona Rattlers of Arena League football and the Oakland Athletics. Apparently, now that everyone’s caught on to that whole 'Moneyball deal', the A’s have run out of ideas on how to cheaply round out their bullpen. After a lengthy phone call with Doug Flutie in which Mrs. Flutie overhears her husband repeat the phrase "Seriously, it’s not that bad up there" a half dozen times, Jay unenthusiastically signs with "Munch-ra-y’all".

Cutler, enjoying the laid-back lifestyle north of the border, immediately puts on 20 pounds but is still the best quarterback in the league by a kilometre. The ‘Al’s’ finish 14-1 (Cutler insisted on playing wide receiver for one game) and waltz to a Grey Cup victory in record setting fashion. Cutler is disappointed when he learns that his league-high salary of $250,000 CAD is worth just $94,276.93 USD after taxes and the foreign exchange conversion.


With no NFL teams vying for his services, and convinced that he had lost money by playing in Canada, Cutler decides to retire and take a job as a colour man on ESPN’s Monday Night Football. Viewers don’t even notice Cutler’s presence until week four.

This Fanpost was written by a Windy City Gridiron member and does not necessarily reflect the ideas or opinions of its staff or community.