I’ll never forget where I was the day the Chicago Bears traded for Denver Broncos quarterback Jay Cutler. It was Thursday, April 2, 2009, early afternoon. I was sitting at my computer in the first apartment I’d moved into after leaving my dad’s house. The layout was simple: two bedrooms connected by a hallway, with a bathroom in between. The living room and kitchen were connected opposite of that bathroom. My roommate, Aaron, was in the other room. We had arranged our desks so that they both faced the same wall, allowing us to glance down the hallway and see each other with just a quick turn of the head. This setup was perfect for coordinating comp stops when we played Warcraft 3.
We were both at our computers, mindlessly scrolling, just passing time until we had to head to work or had to follow up on plans with friends. I remember this part so vividly: the apartment was completely silent, except for the soft clicks of our mice and the quiet whir of scrolling mouse wheels.
Then, without either of us saying a word or missing a beat, like some kind of divine signal, we both looked down the hallway at each other and shouted, “DUDE! We just got Jay Cutler!”

Chicago Bears general manager Jerry Angelo, left, and Bears head coach Lovie Smith, right, pose with Jay Cutler, who was introduced as the new quarterback for Chicago at a news conference on Friday, April 3, 2009, in Chicago, Illinois.
Photo by Phil Velasquez/Chicago Tribune/Tribune News Service via Getty Images
From there, the rest of the afternoon was a blur of excitement. We dove into Jay Cutler highlight reels, theory-crafted what the new-look Bears offense might look like, and immediately edited our Madden rosters to put him in a Chicago uniform. But more than anything, we spent that day fantasizing, dreaming about what it finally meant to have a franchise Quarterback.
When the dust finally settled on the trade, the Bears had sent Quarterback Kyle Orton, a 2009 first-round pick (#18), a 2009 third-round pick (#84), and a 2010 first-round pick (#11) to Denver. In return, they received Quarterback Jay Cutler and a 2009 fifth-round pick (#140).
At the time, I was ecstatic that the Bears had paid that price. A franchise Quarterback for what essentially amounted to two draft picks? (Josh Freeman was taken 17th overall that year, without question, a far less promising choice than Cutler.) In just under two and a half seasons in Denver, Cutler had racked up 9,024 yards, 54 touchdowns, seven game-winning drives, and a trip to the 2008 Pro Bowl. With his natural athleticism, escapability, and elite arm talent, some even dared to compare him to another legendary Broncos Quarterback: John Elway.
This addition instantly quelled fears of a deficiency at Quarterback. Of all fans, Bears fans knew all too well the painful history at the position. Since Sid Luckman hung up his cleats in 1950, Quarterback stability had been more myth than reality in Chicago. There was a brief spark of hope in the ‘80s with Jim McMahon, but injuries plagued his career: he started just 61 of a possible 112 games during his time with the Bears.

A signed Jay Cutler home jersey that is proudly displayed at my residence.
The gunslinger from Santa Claus, Indiana, would go on to set franchise records in completions (2,020), attempts (3,271), passing yards (23,443), touchdowns (154), wins (51), 4th quarter comebacks (16), and game-winning drives (18). He also held the top mark in completion percentage and passer rating, until Mitchell Trubisky eventually surpassed both, though in 51 fewer games.
My excitement for Cutler ebbed and flowed throughout his time in Chicago. Unfortunately, his tenure never quite lived up to the hopes we’d pinned on it. If it wasn’t poor offensive line play, it was a lackluster supporting cast. If it wasn’t that, it was questionable coaching. And when those things weren’t the issue, it was injury or the Quarterback’s own inconsistency. There was always something.
Over time, I came to terms with the type of Quarterback Jay Cutler was. A gifted athlete on the field with top 5 arm talent, who was set in his ways in how he played the game. That very same arm that could win you a game with it’s prowess, could turn around and lose the very next week by throwing multiple costly interceptions. Jay Cutler was a gritty, tough, and frustrating player, whose meme-ability may be unrivaled to this day. He is this franchise’s all-time leading passer, and my all-time favorite Bear.
That begs the question: What free agent or trade were you most excited for? Let us know in the comments!
Gary Baugher Jr. is a rookie contributor to WCG, bringing football insight backed by over 16 years of experience in organized football and more than 30 years as a passionate fan of the game. You can follow him on Twitter at @iamcogs.