Everything I remember about the afternoon Jay Cutler was traded reminds me just how much it meant to Bears fans. I was a college junior, sitting in the newsroom at the Columbia Missourian, pounding away at a keyboard. I can still recall the exact computer I was using when I hit ESPN.com and saw the news on the front page. Not much work got done over the next hour, or for the few after that. I went out with friends that evening and was in such a good mood that I spent most of the night trying not to let it end. I had a flight to Detroit the next morning for the Final Four. It was a miracle that I didn’t miss it.

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All of our NFL preview coverage! The list of attributes that would make Cutler a savior has been rattled off, reorganized, and reiterated so many times that it isn’t worth repeating. Chicago was a quarterback-starved franchise whose futility at the position rivaled that of any team in history; Cutler was a 25-year-old gunslinger fresh off a trip to the Pro Bowl and a 4,500-yard season. Even if there was some concern about the petulance he showed during his last days in Denver, Bears fans were willing to deal with a quarterback who threw fits as long as he could also throw a football.

Somehow, nearly six and a half years have passed since that jubilant April night. From the moment Cutler posed with Lovie Smith and Jerry Angelo for the first time at Halas Hall, the Bears have hired two new head coaches, two new general managers, and five offensive coordinators. Cutler has taken Chicago to the playoffs once, the same number of trips Rex Grossman and Kyle Orton delivered during their seasons as the team’s starting quarterback.

My father always had a handle on quarterbacks in a way I never quite understood. He called it from the start with Ben Roethlisberger, preferred Philip Rivers to Eli Manning, and said that he knew from Aaron Rodgers’s first game that he would be a star. A few minutes after I saw the news of the Cutler trade, I called him from the newsroom.

“Well,” I said, “it looks like the Bears finally got their quarterback.”

“You know,” he said, half talking, half sighing, “I’m not so sure they did.”

As Chicago prepares for its seventh season with Cutler under center, it might be time to admit that my father was right.

The Unlikely Alpha Dog

Knowing what we do now, Ron Jaworski’s stance on the 2006 quarterback draft class makes sense. But at the time, it seemed like a radical notion. The former Eagle joined analysts like Mike Mayock and Steve Young in championing Cutler — and not national champions Matt Leinart and Vince Young — as the best quarterback available that spring. Leinart and Young were four months removed from what might have been the greatest game in college football history, played on the biggest stage imaginable. Cutler’s chance at a bowl game with Vanderbilt ended with a loss to Kentucky. Both Leinart and Young won more games in 2005 than Cutler did in his entire college career.

By the time the draft came, Cutler’s lack-of-college-success narrative had been spun the other way. Everything he’d accomplished at Vanderbilt — where he was the SEC Offensive Player of the Year in 2005 — was done without much help. He’d dragged the Commodores to a win over Tennessee and almost single-handedly taken Florida to the brink. He didn’t have the flashy appeal or name recognition of Leinart or Young, but he did have a killer arm and a willingness to use it. “From a physical skill set, I think Cutler has the biggest arm in the draft,” NFL Network’s Mayock told USA Today at the time. “I think he has a quicker release than either of the other two. He’s tough. I think he played behind a very poor offensive line without a whole lot of help … When I look at that kid and what he did on tape, he can make throws that I don’t think the other two kids can make.”

Reports the week of the draft linked as many as six different teams to Cutler. Titans general manager Floyd Reese had taken advantage of Cutler living just down the road in Nashville and met with him several times. The Jets were rumored to be interested, and their acquisition of the 29th overall pick — from Denver in a three-way trade — gave them the ammunition to move up in the draft. When the time came, though, it was the Broncos who did the dealing. Denver gave up a fourth-round pick to swap places with the Rams and take Cutler 11th overall.

Mile High Mishegas

It took less than three months for Cutler to supplant Jake Plummer, who’d made the previous 46 starts at quarterback for Denver but was mired in the worst stretch of his career. The Broncos were 39-15 in the regular season with Plummer as the starter, but the thought — the one that inspired the drafting of Cutler in the first place — was that the ceiling for their young quarterback was markedly higher.

Cutler’s first two seasons as a starter were promising but unremarkable — then, in 2008, circumstances aligned that made him an attractive and available option. With a porous defense in Denver, Cutler was forced into throwing 616 passes in 2008, which meant pumped-up totals across the board. He threw for 4,526 yards and 25 touchdowns, though he did so while throwing touchdowns less often and averaging fewer yards per attempt. When Mike Shanahan lost his job at the end of the season, the Broncos brought in former Patriots offensive coordinator and offensive wunderkind Josh McDaniels. That’s when the trouble began.

According to what Cutler’s agent, Bus Cook, told the Associated Press, the Broncos were looking to deal Cutler in a move that would bring Matt Cassel with McDaniels from New England. Cutler reacted in the way we’d now expect Jay Cutler to react. He reportedly requested a trade before cutting off communication with McDaniels and owner Pat Bowlen — an accusation Cutler has denied. “I don’t care if you’re talking about trading him for Matt Cassel, Matt Ryan or Tom Brady,” Cook told the AP. “That’s a vote of no confidence in him, and that’s how Jay sees it, and I would, too.” Cutler would say later that he never asked for a trade. McDaniels told the Denver Post, “We don’t want to trade Jay. We never did. He’s our quarterback.” Less than 40 days later, Cutler was gone, off to Chicago for a king’s ransom. As overjoyed as many Bears fans were, the delight didn’t seem to extend to the Chicago locker room, including the notoriously blunt Brian Urlacher.

“I guess the Bears felt like we needed another quarterback, so they made a move,” Urlacher told the Chicago Tribune. “They gave up a lot. Cutler must be pretty good.”

♦♦♦

Jerry Angelo, the Bears general manager for 11 years and the man responsible for bringing Cutler to Chicago, spoke of the trade in the way most Bears fans did. “The rarity of the opportunity makes it unique,” he said to the Chicago Sun-Times. Potential franchise quarterbacks not yet 26 years old don’t become available often. If the Broncos were dangling Cutler, Angelo was at least obligated to call. When it became clear Denver was serious, Angelo was rightly inclined to match its tone. “We felt if we get in it, we have to get in it to win it,” Angelo told the Sun-Times.

The price was steep — two first-round picks, a third-round pick, and Kyle Orton for Cutler and a fifth-rounder — but so was the descent into madness facing the Bears and their fan base if they had to endure yet another era of quarterback mediocrity. The opportunity, as Angelo reminded everyone, was unique.

Windy City Woes

From the start, that first season with the Bears was a nightmare. Cutler threw four interceptions in the opener during a game Chicago lost by only six points. It was only the start of the bad news for Lovie Smith’s group that night. Urlacher’s dislocated wrist meant he’d miss the remainder of the season, and with that, a low point of Smith’s tenure in Chicago began. The Bears defense went from one of the best units in football to a below-average bunch, and Cutler’s ghoulish start against the Packers was only the first of plenty that season. He finished the year with 26 interceptions, throwing multiple picks in seven of his 16 starts.

Heads rolled at season’s end. Ron Turner, unable to coax the most out of his shiny new quarterback, was fired, along with most of his offensive staff. It was the beginning of the cruel cycle the Bears have seen with their offensive coordinators. With Turner gone, Smith turned to former Rams colleague Mike Martz. Smith had finally eschewed the safer option typical of defensive head coaches in favor of a true offensive innovator, a mind more fitting for Cutler’s ability and the Bears’ offensive potential.

Looking back, it was hard to argue. The Bears won plenty in 2010, but most of that success had little to do with Martz and the Chicago offense. A year after trading for Cutler, the Bears made another offseason splash by signing Julius Peppers, who — along with the return of a healthy Urlacher — reignited the Bears defense. Chicago finished fourth in defensive DVOA after dropping to 21st the year before, and it rode that group to an 11-5 record and a division title while the offense sputtered.

The Bears finished in the bottom five in offensive DVOA, mostly due to the epic pounding Cutler took in Martz’s deep-drop, slow-developing system. He was sacked 52 times, the most in the league, and the Bears’ sack rate of 10.1 percent that season is the second highest in football since Cutler arrived in Chicago. Watching the beating Cutler took that year only made the most divisive moment of his Bears career even more complicated.

♦♦♦

There are two moments that will haunt anyone invested in the Cutler era, and the first — famously — came in the NFC Championship Game against the Packers during his second season. After spraining his knee in the first half, Cutler lasted only one series after halftime. The Bears tossed out a worthless Todd Collins before pulling him for Caleb Hanie, and the results were predictable. There was no offense to be had, and the Chicago defense holding Aaron Rodgers & Co. to just 21 points came in vain.

As the Bears stalled over and over, Cutler stood wrapped in a jacket on the sideline, absorbing a barrage of criticism. Darnell Dockett tweeted that if he were a Bear, Cutler would have to “wait till me and the team shower get dressed and leave before he comes in the locker room!” Maurice-Jones Drew was similarly critical. A day later, Mike Ditka and others piled on.

For anyone who’d watched the Bears all season, calling Cutler’s toughness into question was next to impossible. He’d spent most of the year picking grass out of his face mask. “Jay was hurt,” Urlacher said at the time. “I don’t question his toughness. He’s tough as hell. He’s one of the toughest guys on our football team. He doesn’t bitch. He doesn’t complain when he gets hit. He goes out there and plays his ass off every Sunday. He practices every single day. So, no, we don’t question his toughness.”

The knee would have mattered less if not for the thumb. After missing their chance to go to the Super Bowl, the Bears started 7-3 in Cutler’s third season in Chicago. His numbers weren’t demonstrably better than they’d been in his previous two seasons — his completion percentage dipped from 60.4 to 58, with his yards per attempt also taking a slight drop — but there was one key difference. The Bears weren’t turning the ball over. In his 10 starts, Cutler threw an interception on just 2.2 percent of his throws, easily the best mark of his career. With Smith’s defense again finishing near the top of the league, an offense with fewer mistakes was enough to keep Chicago afloat.

The Bears were on their way to their seventh win of the year when Cutler threw an interception late against the Chargers. This play was costlier than just a turnover, though: Cutler was blocked while pursuing the defender and broke his right thumb. He was done for the year. With Hanie forced under center, the Bears finished 1-5 and started what would become a four-year playoff drought.

Reckoning in Chicago

Anyone seeking an excuse for Cutler’s middling play during his first few seasons in Chicago had plenty of places to look. The offensive line was a mess, but his receiving options may have been worse. Johnny Knox was an exciting down-the-field option but little else. Roy Williams was two lifetimes from being a real threat. Rashied Davis was a career special-teams player, and, maybe worst of all, this was the stretch when the Bears were convinced that Devin Hester had a future as a no. 1 receiver.

After a five-game skid without Cutler cost the Bears a playoff trip in 2011, the shuffling really began. Almost the entirety of the Bears’ offensive roster and front office would change over the next two years. Angelo was the first to go. The verdict was still out on his Cutler experiment, but his draft record was etched in stone. He may have delivered a talented quarterback, but from both a personnel and coaching standpoint, he’d done little to give Cutler the best chance to flourish. Former Bears scout Phil Emery was hired as Angelo’s replacement, and he spent the next 18 months making every possible move to transform the franchise into an environment where Cutler could thrive. Emery traded two third-round picks for former Cutler favorite Brandon Marshall, just two months before drafting South Carolina wide receiver Alshon Jeffery.

When that wasn’t enough to jump-start the Chicago offense — and the Bears missed the playoffs despite winning 10 games in 2012 — Emery fired Lovie Smith and replaced him with supposed quarterback guru Marc Trestman. Before the 2013 season, tight end Martellus Bennett and left tackle Jermon Bushrod were signed to significant free-agent deals, and Kyle Long was taken in the first round to help bolster the offensive line. In less than two years, Emery had changed the entire fabric of the Bears organization in an effort to do what Angelo and Smith never could.

In a way, Emery achieved his goal. With Trestman in charge, the Bears offense reached heights it never did under Smith. Marshall was undeniably a star, and Jeffery ascended in his second season. Cutler’s 67.1 QBR was his best mark since his final season in Denver. Still, it wouldn’t have been a year with Jay Cutler if there weren’t some sort of turmoil. After Cutler went down in the middle of the season with a torn groin, career backup Josh McCown posted a 109.0 passer rating, throwing 13 touchdowns to just one interception. When the time came for Cutler to return, there was debate about whether Chicago was right to roll with McCown or hand the keys back to its supposed franchise quarterback. Trestman elected to return to Cutler, but the Bears stumbled down the stretch, dropping a Week 17 game to Green Bay that cost them a trip to the postseason.

10 Years Gone

Even five years in, there was still reason to believe that 2014 would be different for Cutler. He was in his second year of Trestman’s impressive-looking offense, all of whose personnel was returning from the previous season. With Marshall and Jeffery making up one of the best receiver pairings in football, the deficiencies of Cutler’s help seemed to be a thing of the past. Hopeful that with the rest of the pieces in place, Cutler would finally be something close to the player he and others had hoped, Emery handed his quarterback a seven-year, $126 million contract with $54 million in guarantees that gave him the largest cap hit of any player in football. At the time, it was considered the cost of doing business, a notion confirmed with all of the quarterback contracts that have been handed out since. With the outlook for the Chicago offense, Cutler may not have been able to live up to every dollar of the deal, but there was still a chance he’d be the type of franchise quarterback worthy of the going price for one. And that’s what made last season even more of a nightmare.

In his first 10 starts, Cutler threw 12 interceptions. But the dysfunction extended far beyond his play. It got so bad inside the Bears organization that offensive coordinator Aaron Kromer anonymously trashed Cutler to Ian Rapoport of the NFL Network. When it was discovered that Kromer was the source of the comments, it led to a tearful apology in front of the entire team, which Cutler reportedly met with scoffs and head shakes. Trestman eventually benched Cutler for Jimmy Clausen in a move that made little sense and was far too little, far too late. The Kromer story was the cratering point of a disastrous season, which ended with both Emery and Trestman losing their jobs for the same reason so many before them had. They’d put their faith in Cutler, and that faith turned out to be unwarranted.

“I haven’t been able [to coax the best from Cutler] and we haven’t been able to do the things that we want to get done,” Trestman said two weeks before he was let go. “We’re working towards that. But the answer to that is obvious. I’m trying to give you the most truthful answer and that is, we’ve seen moments of it, but it’s not where we need to go. It’s not where we need to be. But it’s not all about Jay. It’s about our entire offense, working together to get it done.”

Despite a handful of other moves that brought the Bears some of their best offensive talent in team history, Emery was gone, too, paying for his decision to tie both his and the franchise’s fortunes to Cutler. And now the new regime of Ryan Pace and John Fox will attempt to do what those before them couldn’t. To new offensive coordinator Adam Gase’s credit, he’s been more tempered than some of his predecessors in proclamations about unlocking the mystery that is Jay Cutler. “Right now, time will tell,” Gase told Dan Wiederer of the Chicago Tribune when asked about Cutler. “If I knew what was going to happen, I’d play the lottery. Right now I don’t know.”

With Cutler’s massive deal still on the books for this season, the Bears were almost certainly tied to him for 2015, and with $10 million of his contract guaranteed for next year, there’s a chance it will be at least another two years before Chicago can realistically move on. Not even the Titans were interested in Cutler when the Bears reportedly called before the draft, and it’s hard to blame them. Six years ago, when Angelo pulled the trigger on the deal to bring Cutler aboard, legendary Chicago sportswriter Rick Telander wrote in the Sun-Times that the Cutler trade “will be the one Angelo rides to enshrinement or out of town on a rail.” It was true for Angelo, and it’s been true for every regime since. Maybe this one will be different. Then again, maybe it won’t.

As for Cutler, there’s no scale for measuring his capacity for boorishness at times of crisis. During a 2011 Sunday Night Football broadcast, he responded to a play call by looking to the sideline and yelling, “Tell Martz I say ‘Fuck him.’” When J’Marcus Webb did all he could to get Cutler decapitated against the Packers early in the 2012 season, Cutler gave Webb enough of a nudge on the sideline to make people take notice. And away from the field, there’s the maybe-apocryphal story — one Cutler hasn’t entirely denied — about him tilting his head back and letting out a deeply apathetic “Don’t caaaaare” as a fan tried to approach him in a bathroom.

For Bears fans, it can all lead to a vexing combination of feelings about a quarterback who seems part insufferable asshole and part quick-witted smartass. We like that Cutler can hold his own on The League, that he’s married to a reality TV star, and that he’s willing to tell off his boss with impunity. When Cutler was stringing together wins for the Bears as they started 7-3 in 2011, I wrote that if Cutler was an asshole, “at least he was our asshole,” doing my best to communicate the complicated process of rooting for a quarterback who could at once infuriate a city while inspiring its fans to come to his defense.

You don’t need to go back very far to find the latest saga in conflicted Cutler fandom. Against the Colts in last Saturday’s meaningless preseason game, after an offseason that featured Cutler being verbally stoned by just about everyone, he bowled over a safety near the goal line as he rumbled toward the end zone. Later that night, a friend of mine said that when Cutler lowered his shoulder, everyone in the room leaped from their seats. For years, through the interceptions, through the body language, and through the fury, Cutler constantly — and at times, maliciously — has found a way to keep Bears fans coming back.