Editor's note: This story originally ran on Oct. 31. The Bears announced Thursday that Cutler will undergo shoulder surgery and be placed on IR, ending his season and perhaps his time with the Bears.

Jay Cutler’s arrival in Chicago was greeted with fanfare typically reserved for sports royalty, but if this is his last season with the Bears, his exit will resemble that of a journeyman quarterback headed to his third team.

What went wrong?

ESPN.com interviewed a former general manager, head coach and offensive coordinator along with analysts and a former Cutler teammate to discuss why a quarterback who holds franchise records for passing yards and touchdowns is expected by many to be released after the season when his guaranteed money comes off the books. And he’s expected to be released despite the fact the Bears have no heir apparent for the most important position on the roster.

Jay Cutler's time in Chicago never has quite worked out the way he or the Bears had hoped. Robin Alam/Icon Sportswire

Rotating offensive coordinators

“All I can go by is what he did with me in Denver, and how he played and how he handled himself -- and you just say, ‘Holy cow!’ and you are kind of surprised it didn’t work out for whatever reasons,” said Mike Shanahan, who coached Cutler from 2006-08 in Denver. “The obvious one is the turnover in coordinators. You are learning a different scheme and a different terminology every time. That is tough on any quarterback.”

But with Cutler, it seems that every theory produces a counter-theory.

Below average The Bears are such a QB-starved franchise that even though Jay Cutler owns many team records, he's been middle-of-the-pack since arriving in Chicago in 2009. Cutler vs. the NFL average since '09 Jay Cutler NFL Avg. Comp pct 61.9 63.5 Yds per att 7.2 7.3 TD-Int ratio 1.4 1.9 Total QBR 58.6 60.7 -- ESPN Stats & Information

“It’s tough for a guy to go through as many offensive coordinators as he had, and I’m pretty sure he’s had a new one every year,” said former Bears Pro Bowl linebacker Lance Briggs, now an analyst for Comcast SportsNet Chicago. “Now, on the flip side, why is it necessary to have a new coordinator every year if one isn’t leaving for a better job? So there is something to be said on both sides of that argument.”

Dowell Loggains is Cutler’s sixth offensive coordinator during his eight years in Chicago. Adam Gase, who spent 2015 with Cutler, was the only one of the previous five to be promoted to head coach when he was hired by the Dolphins. Yes, it’s difficult to keep learning new systems, but is the reason he keeps having to learn new systems because he keeps struggling and getting offensive coordinators fired?

“I think it took a while for him to get used to a different system, and to accept another system and buy in totally to everything that we were doing, whether it was schematically, working on techniques or fundamentals,” said Ron Turner, who was Cutler’s first OC with the Bears in 2009. “Jay is not just the kind of person that is going to come in and automatically trust and believe in everything that you are doing and totally buy in. I’m not sure how quickly that happened. Or if it happened.”

Player evaluation

The highs and lows of Cutler’s career can best be explained through the fundamental task of player evaluation.

“What you have to do correctly is evaluate your own player,” said former Bears general manager Jerry Angelo, who made the trade for Cutler. “If you don't, you will expose their flaws. The key to good coaching is to accentuate on players' strengths, and that starts with accurate evaluations.”

Take your pick Since Jay Cutler joined the Bears in 2009, 24 quarterbacks have thrown at least 2,000 passes. Here are the top five interception percentages: Int. % Mark Sanchez 3.7 Ryan Fitzpatrick 3.4 Jay Cutler 3.3 Josh Freeman 3.3 >>Min. 2,000 att -- ESPN Stats & Information

Except Cutler’s evaluation was more complicated than the Bears imagined.

Cutler is a rare athlete. He possesses the size, arm strength and mobility to do virtually anything on a football field from a physical sense.

But does he possess the mental reflexes that allow a quarterback to scan the field for an open receiver when the reads are not predetermined? Is his decision-making process sharp enough?

“With him, there was really nothing you couldn’t do, to be honest,” Turner said. “I mean, talent-wise, he could make all the throws. His accuracy was good enough to throw for a high percentage. There were not a whole lot of limitations with what you could do with him, physically.”

Good luck finding anyone who disapproved of Cutler’s tape in Denver.

Under Shanahan, Cutler, then 25, made the Pro Bowl in 2008 with a career-high 4,526 passing yards. Complemented by a solid running game, Shanahan often moved Cutler outside of the pocket to reduce sacks. Cutler was sacked 11 times in 616 pass attempts in ’08.

“I looked at Jay as a guy who could not just get us to a Super Bowl but possibly win it,” Shanahan said. “That’s one of the reasons that we drafted him 11th overall in 2006. You looked at all his physical skills -- playing over at Vanderbilt and taking all the shots he did -- and we thought he was a guy with a big upside. I thought the sky was the limit for him.”

So did Turner.

“My evaluation was strictly off film,” Turner said. “I had heard some stuff about concerns about leadership and stuff [which were passed on to the front office], but I was asked just to give my thoughts from the film. It doesn’t take an experienced quarterback guy to look at that and say the guy has talent.

“His arm talent is unbelievable. He can make every throw. His mechanics were different. He had a little bit of a windup, and other mechanical stuff, but a lot of quarterbacks do. They have their own style. But he had the arm talent, the size, the speed and the athleticism. Everything physically is there.”

More than 10 teams originally pursued a deal with Denver for Cutler, who had requested a trade when Shanahan got fired and new coach Josh McDaniels’ flirtation with acquiring Matt Cassel went public and upset Cutler.

The Bears paid a steep price: Denver received a pair of first-round picks, a third-rounder and quarterback Kyle Orton for Cutler and a fifth-round choice. But Angelo said he has no regrets.

“I would do that trade over again and not even think twice about it,” Angelo said. “In my mind, there is no price for a quarterback.”

Hall of Fame executive and ESPN analyst Bill Polian agreed.

“I thought it was a good move,” Polian said. “We had played the Bears in the Super Bowl a few years before [capping off the 2006 season] with Rex Grossman, and it was clear that Grossman wasn’t good enough. I thought the Bears did the right thing by picking up an ascending player.”

Remember, at the time of the Cutler deal, the Bears were not some woebegone franchise. Quite the contrary. Led by Lovie Smith’s Cover 2 defense, which featured a nucleus of future Hall of Famer Brian Urlacher, Charles Tillman and Briggs, the Bears were two seasons removed from back-to-back division titles and the 2006 NFC championship. And under Orton, the Bears finished 9-7 in 2008, narrowly missing the playoffs because of a close loss in Houston in Week 17.

But historically, the Bears struggled to generate consistency at quarterback, which is why the fawning over Cutler inside the city felt appropriate. He was supposed to be the missing piece.

That is where the story took an unexpected turn.

Unrealistic expectations

Turner thought he inherited the quarterback equivalent of a Ferrari, so he wanted to start fast with Cutler. But it took time for Turner to get the right read on Cutler, who passed for 3,666 yards and 27 touchdowns in 2009 but also had a career-worst 26 interceptions and 76.8 passer rating.

Jay Cutler's best year in Chicago arguably came in 2015 with Adam Gase as offensive coordinator. AP Photo/Nam Y. Huh

“With Jay’s talent, probably the mistake I made early with him is that I probably did try to do too much, and then cut back on it as we went, and I think he got better,” Turner said. “But, yeah, probably a little too much, too early. Talent-wise he could do it all, so I said, ‘Oh, God, we can put this in, we can put this in, we can put this in,’ but then reading it, concept-wise, everything else, which was he the most comfortable with? That took a little while to figure that out.”

Turner never had the opportunity to coach Cutler again. The Bears’ 7-9 finish led Smith to install Mike Martz as offensive coordinator.

With Martz, Cutler seemed headed down the same path, throwing seven interceptions over the first six games of 2010, including four in a home loss to Washington.

But as the season wore on, the Bears went a more conservative route on offense, requiring Cutler to do less and instead leaning on the team strengths: defense and special teams.

“You can win with Cutler,” Angelo said. “Sometimes you can win because of Cutler. But most of the time, you are going to win with him, not because of him.”

After reaching that conclusion, Cutler went 25-12 until Smith was fired at the end of 2012.

Identify shift

“It was never necessary to do too much,” Briggs said. “All you had to do was manage the game and keep your defense off the field.

“Plus, you had the greatest return man in NFL history [Devin Hester], and you had the greatest overall special teams unit in the game. A lot of times the offense was getting the ball on the plus side of the football field. So, in the next three plays, you should be in field goal range with one of the most accurate kickers in the NFL in Robbie Gould.”

Life wasn’t perfect in the Smith era. Cutler battled through injuries, probably as a result of the hits he took in the pocket, and the Bears never could settle on a coordinator (Mike Tice replaced Martz in 2012).

But the system worked far more often than it failed.

The team’s fortunes forever changed when former general manager Phil Emery, who succeeded Angelo, installed offensive-minded head coach Marc Trestman in 2013.

The Bears’ identity shifted from defense and special teams to offense, and Cutler, to whom Emery awarded a seven-year extension worth $54 million guaranteed in ’14, became the centerpiece.

Emery did not ignore the defense. He attempted to preserve much of what Smith built, although he didn’t re-sign an aging Urlacher.

But the defense plummeted from fifth overall to 30th. Many of the young defensive reinforcements -- Shea McClellin, Brandon Hardin, Jon Bostic, Ego Ferguson, Khaseem Greene and Brock Vereen -- never became cornerstone players.

Special teams, once an experienced phase, fell off the map entirely. The Bears management went with a largely inexperienced group on special teams, and the results were disastrous for respected coordinator Joe DeCamillis.

There were also issues in the locker room, and chemistry and trust problems with certain players and coaches.

With all the drama swirling around him, Cutler was asked to do more in Trestman’s pass-heavy system.

The Bears won only 10 of 26 games Cutler started under Trestman, and his interceptions spiked back up to 18 in 2014, the highest since his first year in Chicago with Turner. And in a bizarre twist, Trestman, right before he and Emery lost their jobs, benched Cutler for one week in favor of Jimmy Clausen, who is now out of the league.

“Coming off a 10-6 season in 2012, which we should have made the playoffs, we changed the whole focus from what we were doing,” Briggs said. “To me, that wasn’t a recipe for success. And you see what happened. The organization and the team took a hit, went a few steps back, and now the [John] Fox regime is helping the organization recover from it.”

Success with Gase was fleeting

Cutler received a new lease on life when offensive coordinator Gase followed Fox from Denver to Chicago in 2015.

Gase and Cutler clicked instantly, and Cutler posted a career-best 92.3 quarterback rating, tossing only 11 interceptions in 15 starts.

“I really like what Gase did with him,” Polian said. “He got him back to playing a more defensive style of offensive football.”

The Bears were 6-9 under Cutler last season, but he played to mostly positive reviews.

“I’m a huge Adam Gase fan,” former Bears receiver and ESPN analyst Tom Waddle said. “Checking his inner genius at the door was his best decision. He simplified things and didn’t try to reinvent the wheel.

“In 2014, the Bears ran the ball 37 percent of the time. In 2015, they ran it 47 percent of the time. He got Jay out on the edge and took advantage of his athleticism. It wasn’t a surprise to me that a common-sense approach would help Jay play more efficiently.”

Alas, Gase departed to Miami after one season and quarterbacks coach Dowell Loggains was promoted. In the first seven quarters of 2016, Cutler had three turnovers before succumbing to a thumb injury.

Some might consider Cutler to be the ultimate cautionary tale in player evaluations. When used properly, Cutler is good enough to start for a winner. But too often, the Bears treated him like a franchise quarterback, which is a role that might not suit him.

“I look at Jay’s time the same way I partly look at my career there,” Briggs said. “We should’ve given Chicago a championship, or we should have been in the championship game a number of times. We only have ourselves to blame from players on up. We had too good a team for too many years not to make those championship runs.”

Now Cutler’s run might soon be over in Chicago, and the questions about why it resulted in just one playoff win will, to a large part, define his legacy.