He was talented, even though his talent didn’t always serve him well. He was sharp, even if he routinely neglected to wittily muse over a situation. He was surly on the outside, but had a heart of gold to teammates and anyone who he cared to let in. The key word there being “care.” He was flawed and the epitome of an enigma, but was a man who never let his status change who he is.
On this day 10 years ago the Bears sent shockwaves throughout the NFL when they traded for then 25-year-old Jay Cutler. For years the Bears had trudged on with journeyman after journeyman at football’s most important position. They tied themselves to a well-deserved reputation of a place not where quarterbacks go to die — because that would imply the poor quarterbacks they had would’ve excelled as stars elsewhere — but where quarterbacks were never going to amount to anything anyway.
The rocket-armed, gunslinging, improvisational wonder in Cutler was to be different. Cutler represented everything the Bears hadn’t had under center since Harry Truman’s U.S. presidency with the indelible Sid Luckman. Cutler was a legitimate face of the franchise to build around. Someone exciting you could readily associate with the Bears. A boost of energy the Bears franchise hadn’t experienced from the outside in decades. A bold move to put themselves back at the forefront of the NFL’s collective consciousness in an era before social media dominated the sports sphere. It was all Cutler, all the time.
Two years after a painful loss in Super Bowl XLI, the Bears were on the map again thanks to their quarterback.
Who would’ve ever thought of something so utterly preposterous? The Bears, relevant, and thanks to the position that haunted them for most of the 20th century? Stop it. Anyone who would’ve ever brought up the mere possibility of such a ridiculous idea before the Bears traded for Cutler deserved to be mocked.
But that was the thought process behind Cutler’s trade. Despite apparent limitations, Cutler was more than a symbol of new hope for the Bears. He actually gave hope to them.
For many reasons — not all attributable to him — Cutler’s Bears career didn’t pan out the way he and then general manager Jerry Angelo envisioned. In eight seasons at Halas Hall, the Bears made the playoffs just once with Cutler. The Bears were supposed to live up to their famous Monsters of the Midway moniker with him on a consistent basis, but rarely came close to the summit. Most of the time, Cutler’s Bears never came close to that summit as they wasted away at the mountain’s base with a unified tendency for self-destruction. You couldn’t have scripted a more perfectly volatile match of quarterback and team than Cutler and the Bears. The Bears were the NFL’s charter organization plagued by mismanagement they refused to acknowledge. Cutler was the eminently highlighted quarterback who never evolved past his flaws. The two were tailor-made for each other.
Issues of roster management and a stubborn over-reliance on a player who turned out not to be special played major roles in the Bears’ first modern quarterback never living up to insurmountable expectations. Football expectations that were only justified based on what Cutler represented at first, not in who he really was as a player and a person.
You don’t need to be retold Cutler’s tragic ballad of a Bears career and what it represented for both quarterback and team. A complete tell-all novella only serves to beat a dead horse of underlying organizational issues the Bears have had for most of their recent existence. You need only understand how the ripple effects of Cutler’s Bears presence shined on oh so glowingly until it quietly faded away, then curiously rose up again.
You need only recognize how his legacy permeates in the Chicago sports scene almost three years after his last game in a Bears uniform.
One of the strangest things about Cutler’s professional football career was how he was able to become an icon without trying. In retrospect, it was his best talent: Being noticeable without giving any discernible inclination he was putting in effort to do so. Some people aren’t cool, try hard to remedy that, and it shows. Cutler, meanwhile, was the guy in every high school movie that just had to lean against a locker and pop his collar to be cool. Cutler was a walking meme before the proliferation of social media made someone a joke or treasure every day. “Smoking Jay” — a persona rooted out of Cutler’s seeming unwillingness to care about anything meaningful due to what looked like a grumpy cat demeanor — made him a Chicago sports treasure that could be separated from football.
“Smoking Jay” or better yet, Jay, was the biggest piece of who Cutler was as a person. He was the professional athlete at the head of the city’s most popular sports team who perennially looked like he missed his morning coffee. Who looked like he was so oh over the bullshit of his colleagues and competitors and wore that emotion, or lack thereof, on his sleeve.
For this, Cutler became relatable to fans and media members alike. For this, he became the common disgruntled office man who happened to be playing under a beaming hot microscope. Who looked like he never showed you his full hand, when in reality showcased who he was every time he placed himself in the public eye. This is a personality he’s leaned into recently on his wife’s reality show, Very Cavallari, where he’s positioned as the comedic relief of a man who takes his life by the reins in a cavalier fashion. Anyone who took the necessary time to understand Cutler’s essence knows none of this is or ever was an act. It’s the authentic Cutler slightly glitzed up for reality television and nothing more. The genuine “Jay” people in Chicago refuse to let go.
It’s difficult to say for sure without an exact count, but one could venture to guess that Cutler is easily the most written about Chicago professional athlete of the last decade. No one sports figure in the city has had more headlines or newspaper column inches dedicated to them than Cutler. He’s also the most discussed and for a time, had by far the most outside energy invested into each and every single piece of his exploits. Part of that is due to his position as Bears quarterback. Whoever holds the belt of Bears quarterback will always be picked apart.
But most of it is an expression of how Cutler’s image resonates so deeply with those people who were forced to root for and cover him. How they became not only obsessed but downright amused with how he lived his day to day.
The Bears are now squarely in the middle of the Mitchell Trubisky era. They’re invested in his future for the time being. As is a city that will revere him in one moment and tear him down the next, true to form. That Cutler’s memory persists on in the middle of a Bears Renaissance with minimal effort — years after his playing days — speaks volumes as to a Chicago sports legacy that will forever endure.
Robert is the Editor-in-chief of The Blitz Network (subscribe here!), the managing editor of Windy City Gridiron, and writes for a host of other fine publications. You can follow him on Twitter @RobertZeglinski.