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Coming to Terms With the Bears’ Jay Cutler Trade, 10 Years Later

On this week in 2009, Chicago sent two first-round picks, a third-round pick, and Kyle Orton to the Broncos for its new franchise QB. A decade later, it’s time to make sense of the legacy—and logic—of a deal that defined an era of Bears fandom.

Getty Images/Elias Stein

On April 2, 2009, I was sitting in the newsroom of the Columbia Missourian on the campus of the University of Missouri. I would fly to the Final Four in Detroit the next morning, but at the time I still hadn’t packed. All day I’d been tethered to my laptop, repeatedly refreshing the browser. The NFL rumor mill had been churning, and reports suggested that Jay Cutler, the Broncos’ ultratalented 25-year-old quarterback, wanted out of Denver. My hope was that the Bears would go get him.

I can’t remember exactly what time the news broke that afternoon, but when it flashed across my screen—Bears trade for Cutler—I had to stop myself from celebrating in public. I walked out of the building, fist-pumped, and then called my dad. “Dad, we finally have a quarterback,” I remember saying. He paused before uttering four words I’ll never forget: “I’m not so sure.” Back then, I brushed off the words. There was no place for pessimism that day. I spent the next 12 or so hours basking in revelry, to the point that I almost missed my flight.

It’s been 10 years since the Bears sent two first-round picks, a third-round pick, and Kyle Orton to the Broncos in exchange for Cutler. In that time, it seems as though the narrative surrounding both the deal and Cutler’s career in Chicago has been warped. Cutler’s personality has made him the perfect reality-show curiosity, but the same quirks made him an enigma during his playing days. Smokin’ Jay may have always looked like he didn’t give a fuck, but Chicagoans gave many when we first heard he was coming to town.

Nearly 90 years into their existence, the Bears were arguably the most quarterback-starved team in NFL history. The franchise’s all-time leading passer upon Cutler’s arrival was Sid Luckman, who retired in 1950—five years before my father was born. Next on the list was Jim Harbaugh, who was the Bears’ full-time starter for only four seasons. Six years before trading for Cutler, Chicago held the no. 4 pick in the 2003 draft on the heels of a 4-12 season with a rotating cast of Jim Miller, 37-year-old Chris Chandler, and future CFL legend Henry Burris at QB. Desperate for a franchise passer, the Bears traded down from no. 4 to no. 22 and selected Florida product Rex Grossman. Imagine that happening today—a team in need of a quarterback trading back in the first round to find its guy. Five maddening years later, Grossman lost the gig to 2005 fourth-round pick Kyle Orton, and the Bears were once again mired in quarterback mediocrity with no clear way out.

By 2009, the front office also had plenty of motivation to find a jolt of energy. In the 2006 season, the Bears had gone 13-3 and made the Super Bowl, but the needle was beginning to point in the wrong direction. Five years into head coach Lovie Smith’s tenure and nearly a decade into general manager Jerry Angelo’s stint, Chicago needed a shot in the arm. And that’s precisely what a 25-year-old Pro Bowl quarterback could provide.

Cutler threw for 4,526 yards during the 2008 season, third in the NFL behind Drew Brees and Kurt Warner. He also tossed 25 touchdowns while averaging 7.3 yards per attempt. Those numbers seem modest compared with today’s lofty standards, but a decade ago they were well above average. Last season 20 QBs hit at least the 7.3 yards-per-attempt mark; in 2008, Cutler was one of only 10 to do it. And while nearly every NFL team has a long-term plan in place at QB heading into the 2019 season, that was far from the reality 10 years ago. The 10 teams with legitimate franchise passers were an anomaly in a league where Orton, Tyler Thigpen, Jake Delhomme, JaMarcus Russell, Shaun Hill, Kerry Collins, Jeff Garcia, Gus Frerotte, Trent Edwards, Derek Anderson, and—yes—Ryan Fitzpatrick were all starters. Denver finished no. 1 in Football Outsiders offensive DVOA in 2008. Prying away a passer who could guide the NFL’s most efficient offense because of a tiff with his new head coach—no matter how many draft picks it cost—seemed like a no-brainer for Chicago.

But then Cutler’s first season with the Bears left a lot to be desired. He threw 26 interceptions in 2009 for a team that finished 7-9 and averaged just 20.4 points per game. Before the deluge of picks came, the team was so enamored of its new quarterback that it handed Cutler a contract extension, despite his having two years remaining on his rookie deal. I’ll dive more into his penchant for interceptions—and make the requisite Jay Cutler Apology Tour—shortly. First, though, it’s important to establish that while to the fan base Cutler represented the franchise quarterback they’d always lacked, to the front office he represented a relative financial bargain.

In 2011—two years into Cutler’s new deal and the first year of available cap hit data on Spotrac—Cutler carried a cap hit of just $9.5 million. That was the 42nd-highest mark in the league and the 11th-highest among quarterbacks. The following year, Cutler was tied for ninth at the position and 43rd leaguewide, just behind Bears linebacker Brian Urlacher. Cutler’s production in the early years of his deal never matched that of the top QBs in the league, but he also wasn’t paid like one. Chicago’s financial folly in regard to Cutler wouldn’t come until later.

Now for the Cutler Apology Tour. Belaboring this point would lead readers to accuse me of being a delusional fan incapable of facing the reality that Cutler was an infuriating, mistake-prone quarterback who sabotaged the Bears’ chances more often than he elevated them. But some key context has been lost over the years. Following his interception-filled 2009 campaign, Cutler turned in a string of solid seasons for Chicago without much of a supporting offensive cast to lean on. As the Bears went 11-5 in 2010 (thanks largely to a defense that allowed just 17.9 points per game), Cutler’s top two receivers were Devin Hester—whom Chicago was still trying to force into a role on the offense—and speedster Johnny Knox. By that point, offensive coordinator Mike Martz had done all he could to limit star tight end Greg Olsen’s role. Martz’s system also consistently put his QB in harm’s way. Cutler was sacked a league-high 52 times that season. Even if you remove the October game against the Giants in which he was sacked 10 times (and a record nine times in the first half), Cutler still would have led the league in sacks taken. The Bears’ two starting offensive tackles in 2010, rookie seventh-round pick J’Marcus Webb and botched free-agent acquisition Frank Omiyale, graded out as two of the worst pass-blocking tackles in the league.

The punishment Cutler took that year was relentless, which is why the guff he took for sitting out during the second half of the following January’s NFC title game always seemed misguided. A sprained knee sidelined Cutler against Green Bay, and the Caleb Hanie–led Bears lost to the Packers in a 21-14 heartbreaker. Cutler’s injury and the ensuing result were one of several sliding-doors moments from his tenure in Chicago. The following season the Bears started 6-3 heading into a Week 11 clash with the Chargers at Soldier Field. Chicago was nursing a 31-20 lead and on its way to gaining a stranglehold on the NFC wild-card race when Cutler threw an interception in the left flat to Antoine Cason. To prevent a pick-six, Cutler hurled his body toward Cason and knocked him out of bounds at the 16-yard line. While the Bears held on for the win, it was a pyrrhic victory. Cutler’s right thumb was broken; he’d miss the final six games of the season, a stretch that saw the Bears lose five straight and their playoff chances under Hanie.

Another 10-6 season followed, but yet another year without a playoff berth cost Lovie Smith his job. Then came the truly devastating mistake of the Cutler era. Even as backup quarterback Josh McCown performed admirably in the injured Cutler’s stead under first-year head coach Marc Trestman in 2013, the Bears elected to hand Cutler a seven-year, $126.7 million contract extension in 2014. Gone were the days of Cutler’s tolerable cap hits. That fall, his $18.5 million cap figure was the sixth-highest in the league. Fewer than 12 months after signing Cutler to the deal, general manager Phil Emery, along with Trestman, was fired.

For many, the Cutler era in Chicago is a punch line that includes cigarettes and stories at the urinal. Even amid all the interceptions and misanthropy, though, it’s hard to look at the trade a decade later and think that the Bears made the wrong move. It wasn’t Angelo’s fault that Emery decided to hand Cutler a massive extension rather than snag one of the several promising QBs available with the 14th overall pick in 2014 (Teddy Bridgewater, Derek Carr, and Jimmy Garoppolo, to name a few). When Angelo made the move in 2009, he did so with nearly a century of shoddy QB play in the rearview mirror, for a franchise desperate to fill the most important position in sports.

I won’t say that I remember the Jay Cutler era in Chicago fondly. But revisionist history won’t taint my memories of rejoicing on that day in April 2009. If I could go back, I’d make the trade again every single time.