When the Chicago Bears won Super Bowl XX in January of 1986, it marked the crowning achievement for one of the best defenses ever. 

The Bears went 15-1 in the regular season and allowed just ten points in the postseason, all of which came to the New England Patriots in their 46-10 Super Bowl blowout.

Quarterback Jim McMahon was perhaps the biggest beneficiary of the elite defense along with Hall of Fame running back Walter Payton in McMahon’s backfield. McMahon finished the 1985-86 season with an 11-0 record as a starter, missing five games with various injuries. Despite this, he recorded a career-high 2,392 passing yards and 15 touchdowns. McMahon was named to his first and only Pro Bowl as a result.

In the modern NFL, McMahon would be considered a “game manager,” as he was competent enough at quarterback to rely on a solid rushing attack and elite defense to lead the way while he just had to play mistake-free football. 

This is an effective strategy when you have an elite defense and rushing attack. The Bears were even able to utilize it again when they made it to Super Bowl XLI with Rex Grossman (more on him later). The problem is that all the other times when you don’t have an elite defense and/or rushing attack, and you rely on a quarterback to win your games, your quarterback can’t get the job done. This is an issue the Bears have faced almost constantly since the Super Bowl victory all those years ago.

With the Bears selecting Caleb Williams with the first overall pick in Thursday’s NFL Draft, let’s look back at the history of Bears signal-callers since McMahon’s departure. 

Mike Tomczak and Jim Harbaugh


Still fueled by the success of Super Bowl XX, the Bears made it back to the NFC Championship to cap off a strong 1988 season and welcomed the San Francisco 49ers to Soldier Field in what would ultimately be McMahon’s last stand. The offense sputtered, and the seventh-year quarterback was benched for Tomczak en route to a 28-3 loss.

The offseason saw disputes between McMahon, Bears ownership, and head coach Mike Ditka, which ultimately ended up seeing the former Super Bowl Champion shipped off to San Diego. Tomczak, who had been with the Bears since 1985 as an undrafted free agent, was named the starter going into 1989. Tomczak had started games in the past as McMahon was out with injuries, but the 1989 season was his first at the top of the depth chart.

His time on top would be short-lived, though. Tomczak started 11 of Chicago’s 16 games in 1989, and Harbaugh started the other five. Tomczak threw for 2.056 yards and 16 touchdowns to 16 interceptions, and by the time the offseason rolled around, Bears management chose to go with Harbaugh.


Before he was 2024 College Football Playoff National Championship-winning Michigan Wolverines head coach Jim Harbaugh, he was Michigan Wolverines quarterback Jim Harbaugh. Harbaugh’s prolific Michigan career broke program records and ended with a third-place finish in the 1986 Heisman Trophy voting.

Despite having McMahon and Tomczak already, the Bears selected Harbaugh with the 26th overall pick in the 1987 NFL Draft. Like Tomczak, Harbaugh saw time in limited capacity before getting the starting job in 1990. But once he got it, he brought stability back to the role. 

Harbaugh started 14 of Chicago’s 16 games in 1990 before a shoulder injury cost him the final two games of the season and the Bears’ two playoff games, as Tomczak took the job back for those four games. The season ended with a 31-3 loss to the New York Giants. Still, Harbaugh’s 2,178 yards, ten touchdowns, and six interceptions, hilarious numbers by modern standards, were good enough to make him the long-term starter, and Tomzcak signed with the rival Green Bay Packers in the offseason.

The 1991 season was Harbaugh’s best with the Bears, by far, as he became the first Bears quarterback in nearly a decade to start all 16 games, throwing for a career-high 3,121 passing yards and 15 touchdowns, though he did have 16 interceptions as well. Chicago made it back to the playoffs, but Harbaugh struggled in the 17-13 Wild Card Round loss to the Dallas Cowboys, throwing three interceptions.

Unfortunately for Harbaugh and Chicago, the bottom fell out in 1992. The Bears went 5-11, and he started 13 of the team’s 16 games, with two of the three missed starts coming amid a six-game losing streak. After Harbaugh lost four in a row late in the season, Ditka turned to backup Peter Tom Willis to get things back on track.

Willis lost both games, pushing the losing streak to six, and ultimately was the final nail in the coffin for Ditka, who would be fired after the 1992 season, ending his 11-year run with the team.

The Bears hired Dave Wannstedt to replace Ditka and hopefully help restore the team to the glory of the mid-80s. Unfortunately, his first year didn’t go great. Harbaugh started 15 games but struggled to get anything going en route to the team’s 7-9 finish. Harbaugh threw for just seven touchdowns to 11 interceptions and left the Bears in free agency in the offseason. After a brief period of stability, Chicago was back to square one.

Steve Walsh and Erik Kramer


With Harbaugh now in Indianapolis and a new head coach at the helm, the Bears signed a pair of free-agent quarterbacks to compete for the job: Steve Walsh and Erik Kramer.

Kramer was named the starter coming out of training camp. He had been the starter for the Detroit Lions off and on since the start of the 1991 season when he returned to the NFL after a three-year stint with the CFL’s Calgary Stampeders after appearing in three games with the Atlanta Falcons during the NFL’s 1987 player strike.

Due to injuries and inconsistent play, Kramer would only start five games in 1994, going 1-4. Walsh would fare much better, going 8-3 in his 11 starts and leading the Bears to the postseason in Wannstedt’s second season.

The coach’s lone playoff win in his six seasons at the helm came when Walsh led the Bears to a 35-18 victory over the Minnesota Vikings in the Wild Card Round before the team got blown out by the eventual Super Bowl champion San Francisco 49ers in the Divisional Round.  


Despite the postseason appearance, the Bears went back to Kramer for the 1995 season, and this time, they stuck with him. The former North Carolina State Wolfpack standout started all 16 of the team’s games, and while the Bears finished 7-9, he had the best season by a quarterback in Chicago Bears history, throwing for a franchise single-season record 3,838 yards and 29 touchdowns, both of which still stand as the franchise’s single-season records to this day.

That’s right. The Bears have never had a 4,000-yard passer or had a quarterback throw 30 touchdown passes in a season.

Unfortunately for Kramer, he could not continue his success in the 1996 season. He suffered a season-ending neck injury just four games into the campaign, leaving the Bears to sign 38-year-old Dave Krieg, best known for his 12 years and three Pro Bowl appearances with the Seattle Seahawks. The aging veteran was inconsistent in his 12 games, throwing for 2,278 yards and 14 touchdowns to 12 interceptions as the Bears finished 7-9.

With Kramer’s injury status up in the air entering the 1997 season, the Bears traded their first-round pick to the Atlanta Falcons in exchange for former Notre Dame Fighting Irish standout Rick Mirer. By the start of the season, though, Kramer was named the starter. It went poorly. The team started 0-3, and Mirer was tabbed to replace Kramer, but they also went 0-3 as a starter, leading to a Week 7 return for Kramer, which the Bears also lost to start the season 0-7.

They would rally to a 4-12 season, and Kramer eclipsed the 3,000-yard mark again, finishing with 3,011 yards, making him the first Bears quarterback ever to have multiple 3,000-yard seasons, but he also had 14 touchdowns to 14 interceptions.

By the time the 1998 season came around, the writing was on the wall for both Wannstedt and Kramer. The quarterback started the first eight games of the season, going 3-5, but injured his shoulder in the team’s 23-20 win over the Tennessee Oilers, ending his season and Bears career.

Chicago turned to Steve Stenstrom, who struggled in seven games with the Bears going 1-6 and throwing just four touchdown passes over seven games. Moses Moreno started the season’s final game and also lost, putting the team at 4-12 for the second straight season.

The Bears fired Wannstedt after the season. In addition to his one playoff win, he won just one game against the rival Packers in 12 attempts. As the calendar flipped to 1999, the Bears again needed a new coach and quarterback.

Cade McNown, Jim Miller, Shane Matthews, Chris Chandler, Kordell Stewart


Most NFL coaching searches are cut and dry. You identify a pool of candidates, interview them, pick one, and hire them.

After firing Wannstedt, the Bears did 95% of that. They identified former Chicago linebackers coach and then-Arizona Cardinals defensive coordinator Dave McGinnis as their top choice interviewed him, picked him, and hired him. The one issue? Bears president Michael McCaskey announced that McGinnis had been hired without actually coming to an agreement with the coordinator.

McGinnis understandably withdrew his name from consideration, while McCaskey had to face the media with egg on his face. Finally, a month after firing Wannstedt, the Bears had their new (second choice) coach: Dick Jauron, an Illinois native who was then the defensive coordinator of the Jacksonville Jaguars.

With the new head coach in place after an embarrassing search, the focus shifted to the 1999 NFL Draft. The Bears held the seventh pick, unfortunately too low to be in contention for Chicago native Donovan McNabb, Tim Couch, or Akili Smith. As such, the Bears traded with Washington to move down from No. 7 to No. 12 and selected UCLA quarterback Cade McNown, one pick after division rival Minnesota selected Daunte Culpepper. 

To say McNown’s two seasons with the Bears didn’t go well would be an understatement. In the 1999 season, McNown’s rookie campaign saw him appear in 15 games, with six games starting for the Bears and the last three of the season. McNown split time with Shane Matthews and Jim Miller in his rookie season (more on both of them in a bit), and he threw for 1,465 yards and eight touchdowns to 10 interceptions.

Despite the struggles, the Bears returned to McNown for the 2000 season. He appeared in 15 games again and started nine this time. The Bears went 1-8 in games the former UCLA quarterback started, and by the end of the season, Jauron had to bench the second-year QB, fearing a revolt from the team if McNown continued as a starter. McNown would go on to be traded to the Miami Dolphins in the offseason but would never play another NFL snap.

Two seasons after using a first-round pick on a quarterback, the Bears were again looking for another one.

With McNown out of the picture to start the 2001 season, the Bears elected to turn to Miller over Matthews, despite Matthews having made 12 starts over the past two seasons to Miller’s five. The decision paid off for Jauron and the Bears, though, as Miller made 13 starts and, along with AP Offensive Rookie of the Year running back Anthony Thomas and the league’s top-ranked defense, led Chicago to a 13-3 season and their first trip to the playoffs since 1994. 

Unfortunately, the playoff trip ended in disappointment as Miller got injured early in the second quarter of Chicago’s Divisional Round matchup against McNabb and the Philadelphia Eagles. It was 6-0 when Miller went down with the injury, and Matthews threw for just 66 yards and a pair of interceptions in relief as the Bears fell 33-19 in what would wind up as Jauron’s only playoff appearance as head coach. However, Miller had a career-best season as a quarterback, throwing 2,299 yards and 13 touchdowns.

As has been the case more often than not when they’ve made the playoffs in the past four decades, the Bears could not turn 2001’s success into anything of note. Matthews left the Bears in free agency for Washington, where he reunited with Steve Spurrier, his coach when he was with the Florida Gators. Former Atlanta Falcon and two-time Pro Bowler Chris Chandler signed with the Bears in free agency, despite Chandler’s best years being behind him, not unlike when the team acquired Krieg. 

Miller was the starting quarterback going into the 2002-03 season, but inconsistent play combined with injury issues saw him start eight games while Chandler started seven (Henry Burris started the other game, his lone NFL start before going on to have a tremendous career in the Canadian Football League). Neither Chandler nor Miller played exceptionally well for the Bears, who went 4-12 and returned to the cellar of the NFC North a year after winning the division.

Miller went 2-6 in his starts, throwing for 1,944 yards and 13 touchdown passes to nine interceptions, while Chandler went 2-5 in his starts, throwing for 1,023 yards and just four touchdowns to four interceptions. 

The Bears faced an interesting decision in the 2003 NFL Draft. Should they try again with the aging Chandler? Should they turn the starting job over to former Pittsburgh Steeler Kordell Stewart, who they signed in free agency, or should they try, yet again, to draft a quarterback?

Chicago held the fourth pick going into the 2003 Draft. Still, after Carson Palmer came off the board first overall, the Bears were willing to trade back, sending the fourth pick to the New York Jets for No. 13 and No. 22. They would go on to select Penn State defensive end Michael Haynes 13th. With the 22nd pick in the 2003 NFL Draft, the Chicago Bears selected Florida Gators quarterback Rex Grossman.

The 2003 season featured many of the hallmarks you’ve come to expect from the Bears at this point in the column. Inconsistent play and injuries led to each of the three quarterbacks making multiple starts in the season, with Stewart opening the year as the starter, getting benched, and then being brought back as the starter when Chandler was just as bad.

By the final three games of the season, the team was eliminated from playoff contention, and Jauron, likely knowing he would be fired by the end of the season, turned to Grossman.

Grossman picked up two wins in the three games and threw for 437 yards, two touchdowns, and an interception. Not mind-blowing, but compared to Stewart and Chandler’s combined 2,468 yards, 10 touchdowns, and 19 interceptions over the season’s first 13 games, Grossman offered a glimmer of hope that maybe the franchise had finally found a long-term answer at quarterback.

Unfortunately, it hadn’t.

Rex Grossman, Chad Hutchinson, Jonathan Quinn, Craig Krenzel


After firing Jauron, the Bears tabbed St. Louis Rams defensive coordinator Lovie Smith as their next head coach. It was much less dramatic than last time, though it did later come out that had the front office been willing to meet his rumored $4 million price, they would have hired Nick Saban instead.

With Chandler and Stewart being released in the offseason, it was clear that Smith and the Bears planned to go with Rex Grossman as the starting quarterback. 

After splitting the first two games of the season, losing to the Detroit Lions but defeating the Green Bay Packers, disaster struck for Grossman, as he suffered a season-ending torn ACL after being tackled on a scramble against the Minnesota Vikings. The Bears would lose the game and turn to Jonathan Quinn to start the next three games. Quinn, who had started just three NFL games since 1998, struggled to acclimate and went 0-3 in his three starts. Smith was suddenly 1-5 to begin his NFL career.

Knowing a change was due, Smith benched Quinn for former Ohio State quarterback Craig Krenzel. While Krenzel’s numbers were unspectacular, he would go on to win the next three games for the Bears, bringing the team to 4-5 before a loss to Peyton Manning’s Indianapolis Colts, coupled with a Thanksgiving Day loss to the Dallas Cowboys, where Krenzel suffered a season-ending ankle injury essentially ended the team’s playoff hopes.

Krenzel had three touchdowns and six interceptions over his five starts but made essential plays in big moments to keep the Bears in the game. Quinn replaced Krenzel in the loss to Dallas, but Smith turned to Hutchinson for the final month of the season, marking the fourth starting quarterback of the season.

Hutchinson ended up with the best numbers of any Bears quarterback of 2004, throwing for 903 yards and four touchdowns to three interceptions in five starts, but the team went just 1-4 in the starts, bringing them to 5-11 to end Smith’s first season.

Kyle Orton, Rex Grossman, Brian Griese


The Bears used the offseason to purge their quarterback room, getting rid of Quinn and Krenzel and monitored Grossman’s ACL recovery. They also drafted Purdue’s Kyle Orton in the fourth round of the 2005 NFL Draft, just in case Grossman’s durability concerns didn’t improve.

Heading into training camp, it looked like Grossman would be the starter, and Hutchinson would serve as his backup, with Orton as a third-string option. Then, disaster struck again for Grossman. 

In the first half of a preseason game against the Rams, the second-year quarterback suffered a broken ankle that would keep him out for most of the season. Hutchinson’s preseason performances were uninspiring, and Smith and the Bears decided to name Orton the starter, cutting Hutchinson and signing Jeff Blake as a backup.

Armed with a solid rushing duo of Thomas Jones and rookie Cedric Benson, plus the league’s best defense, Orton was surprisingly effective in his first season. After going 1-3 in their first four games, Orton and the Bears won eight in a row to move to 9-3. Orton was tasked with two simple tasks: Don’t turn the ball over and lean on Jones and Benson.

Orton did just that over his 15 starts, throwing for 1,869 yards and nine touchdowns to 13 interceptions, but six of the interceptions came in the first three games of the season. Grossman returned for the Bears’ 24-17 Christmas Day win over the Packers, where the team clinched the NFC North, but that was his lone appearance of the regular season.

At 11-5, the Bears were back to the playoffs for the first time since 2001. They hosted the high-powered Carolina Panthers offense. Grossman made the start and went just 19-for-42 with 192 yards, a touchdown, and an interception. It likely wouldn’t have made a difference if Orton started, as Steve Smith went off for 12 receptions, 218 yards, and a pair of touchdowns in the 29-21 Panthers victory.

While the Bears went one-and-done in the playoffs, it was clear that if they could go 11-5 with a fourth-round rookie at quarterback, they could likely be on to bigger and better things.

The Bears took an interesting approach in the 2006 NFL Draft. They sent the 26th pick to Buffalo for the Bills’ second and third-round picks, then selected Miami Hurricanes cornerback Devin Hester with their own second-round pick. At the time, Hester was known as a prolific punt returner for the Hurricanes, recording six kick or punt return touchdowns in his time with Miami.

The Bears hoped Hester’s proficiency in special teams could help shorten the field for Grossman and the offense in the 2006 season, and they couldn’t have been more correct.

Grossman finally felt like he arrived in 2006, starting all 16 games for the Bears en route to a 13-3 finish, their best since 2001. Grossman’s play was inconsistent at times, resulting in 20 interceptions, but he made up for it by throwing for 3,193 yards and 23 touchdowns, resulting in the best season by a Bears quarterback in over ten years.

Hester played his role exceptionally, coming away with six punt or kickoff return touchdowns in the season, and the Bears defense was ruthless, coming away with 24 interceptions and 40 sacks on the season.

The defense and Hester were fully displayed in Chicago’s Week 6 Monday Night Football win over the Arizona Cardinals. Grossman struggled, but thanks to a monster performance by linebacker Brian Urlacher, a pick-six by cornerback Charles Tillman, a scoop and score by safety Mike Brown, and an 83-yard punt return touchdown by Hester, the Bears were able to overcome a 20-point halftime deficit to steal a win and improve to 6-0 to start the season.

Heading into the postseason, the Bears were compelled to exorcise the demons of 2001 and 2005. They hosted the defending NFC Champion Seattle Seahawks in the Divisional Round and came away with a 27-24 overtime victory before hosting the New Orleans Saints in the NFC Championship. The Bears got out to a 16-7 halftime lead, but the Saints pulled within two on their first drive of the second half after Reggie Bush took an 88-yard screen pass.

That would be the last time New Orleans scored during the game, as the Bears scored 23 unanswered points to come away with a 39-14 victory and finally head back to the Super Bowl.

As you likely know, Super Bowl XLI didn’t go well for Chicago. Hester returned the opening kickoff for a touchdown. Prince was excellent in the halftime show, but with the Bears down 22-17 early in the fourth quarter, Grossman threw a pick-six to cornerback Kelvin Hayden, effectively ending the game and giving the Indianapolis Colts their franchise’s second Super Bowl victory.

Despite coming up short, there was still a lot for the Bears to look forward to heading into the 2007 season. Grossman played an entire season without any injury concerns. The team selected Miami tight end Greg Olsen as their first-round pick, and they had just made the playoffs for back-to-back seasons for the first time since the early 90s. Could this turn the franchise around and make them annual contenders?

Unfortunately for the Bears, no it could not. With defensive coordinator Ron Rivera having departed the team to take the same position as the San Diego Chargers and playing a first-place schedule, the Chicago defense took a big step back, as did Grossman.

Grossman started the first three games of the season and threw six interceptions, leading to his benching in favor of backup Brian Griese. Unlike most Bears backups we’ve covered, Griese came in having started 72 games with the Miami Dolphins, Denver Broncos, and Tampa Bay Buccaneers before signing with Chicago.

Griese took over for the next six games, going 3-3 in his starts. Like Grossman, Griese also was plagued with turnovers, throwing ten interceptions over the six starts.

After Griese suffered an injury in Chicago’s Week 10 win over the Raiders, Grossman was named the starter again. He managed to keep his interceptions under control, throwing just one over the four starts he made, though he did lose three fumbles, and the team went 1-3 in that stretch, with all three losses being by one possession.

Grossman suffered a season-ending knee injury in a loss against Washington. Griese came in in relief in the loss. With the Bears out of playoff contention, Smith turned to Orton for the final three games of the season. Orton went 2-1 and brought the disappointing season to a 7-9 finish. 

After the season, Griese was traded back to Tampa, and the Bears went into 2008 deciding between Orton and Grossman as starter.

Unlike when Grossman missed the whole season and waltzed back in to take the starting job, Smith decided to go with Orton this time. It proved a great decision, as Orton started 15 of 16 games, missing a mid-season contest with the Lions after an ankle injury. 

The second round of the 2008 NFL Draft saw the Bears find another player who would heavily contribute to the offense over the next decade — Tulane running back Matt Forte. Forte rushed for a franchise rookie record 1,238 yards and added nearly 500 receiving yards to finish his rookie season with 1,715 yards from scrimmage, breaking another Bears franchise record.

Going into the season’s final week at 9-6, the Bears had a chance to make it back to the playoffs if they could beat the Houston Texans. Unfortunately, they came up short and lost 31-24 despite two touchdown passes and a rushing touchdown from Orton, who finished the season with 2,792 passing yards, 18 touchdowns, and 12 interceptions.

If nothing else, maybe the Bears had finally found a long-term solution at quarterback in Orton.

Or had they?

Jay Cutler, Caleb Hanie, Josh McCown, Matt Barkley, Brian Hoyer


Jay Cutler was supposed to change everything. 

Shortly before the 2009 NFL Draft, the Bears made a surprisingly aggressive trade, packaging Orton and multiple first-round picks to the Denver Broncos for 2008 Pro Bowl quarterback Jay Cutler. Grossman had left in free agency so that it would be Cutler’s team.

It was Cutler’s team and Cutler’s offense. Over the years, Bears fans would learn that that came with higher highs than many have experienced in the past three decades, and while there would still be lows, they would hopefully not be as bad. 

Cutler’s 2009 season was a mixed bag. The Bears went 7-9 and missed the playoffs again, and Cutler had a league-high 26 interceptions, but he also had, at the time, the second-best season a Bears quarterback has ever had in terms of both passing yards (3,666) and touchdowns (27).

While the interception numbers were alarming, they mostly came in bunches. Fifteen of Cutler’s 26 interceptions were spread out over just four games, throwing five against the 49ers, four against the Packers, and three each against the Cincinnati Bengals and Baltimore Ravens.

The Bears went a disappointing 7-9 in Cutler’s first season but threw eight touchdown passes over the final two games of the year to inspire hope and confidence heading into 2010. Most importantly, he started all 16 games, bringing consistency to the position.

Smith and the Bears started the offseason with a bang, relieving defensive coordinator Bob Babich and offensive coordinator Ron Turner of their duties and bringing in former Detroit Lions head coach Rod Marinelli to run the defense and former St. Louis Rams head coach Mike Martz, whom Smith worked with during his time with the Rams, to run the offense. 

Marinelli turned the defense back into a top-five unit in the league, and Cutler cut his interception total from 26 to 16, adding 23 touchdowns and 3,274 yards along the way. He started 15 of 16 games for the Bears, missing the second half of Chicago’s Week 3 loss to the New York Giants with a concussion after being sacked nine times in the first half and missing the team’s next game against the Panthers (journeyman backup quarterback Todd Collins picked up the victory in that game).

Cutler returned to action after the win over Carolina, and the Bears lost the next two games but would go on to win seven of their last nine to finish the season at 11-5 and winning the NFC North for the third time under Smith.

Just like the last time they made the Divisional Round, the Bears hosted the Seahawks and came away with a 35-24 victory in Cutler’s postseason debut, which saw the quarterback put four touchdowns (two passing, two rushing) on the board in the win. The only thing between Cutler and the Bears heading back to the Super Bowl was the vaunted Green Bay Packers.

Cutler was playing well against the Packers, picking his spots and not trying to do too much. Cutler took an awkward hit early in the second half, resulting in a sprained MCL. This also led to former players and media members taking to social media to question Cutler’s toughness, which would plague the quarterback for years.

After putting Collins in to back up Cutler, the offense continued to sputter, and Collins suffered a shoulder injury late in the third quarter. Down 14-0 and out of options, Smith turned to third-string quarterback Caleb Hanie. Shockingly, it worked out at first. Hanie moved the ball much easier than the other two quarterbacks, with a 33-yard pass to Johnny Knox setting up a Chester Taylor touchdown run that got Chicago on the board and made it a one-possession game with 12 minutes to play.

It remained 14-7 until there were roughly six minutes left, and Packers defensive tackle BJ Raji stepped in front of a pass and took it to the end zone to put Green Bay up 21-7.

Hanie answered back immediately, leading the team on a four-play touchdown drive to bring the Bears back within seven with five minutes to play. Chicago forced a stop on defense, and Hanie drove the team into Green Bay territory, but Packers cornerback Sam Shields sealed the game with an interception, and the Packers went on to win Super Bowl XLV over the Steelers.

Change came for the offense in the offseason, as the Bears traded Olsen to the Panthers for a third-round draft pick. Long thought to be a Martz call, which he has since denied, the decision was confusing at the time and is even more bizarre with the benefit of hindsight, as Olsen went on to play nine seasons for the Panthers and rack up nearly 7,000 receiving yards for the team. 

Martz has since denied having anything to do with Olsen’s departure. Still, it led to a fractured relationship between Cutler and the offensive coordinator, which likely accelerated Martz’s departure from Chicago.

Despite losing Olsen, Cutler and the Bears clicked on all cylinders through the season’s first two months. Heading into a Week 10 showdown with the Chargers, the Bears sat at 6-3, and Cutler had seemingly matured and evolved as a quarterback, throwing just six interceptions over the first nine games.

With the Bears up 31-20 in the fourth quarter against San Diego, Cutler threw an interception, then did the absolute worst thing a quarterback could do after throwing an interception: He tried to make a tackle. The attempted tackle slowed Chargers cornerback Antoine Cason down, and Matt Forte prevented the touchdown. The issue? The tackle caused Cutler to break the thumb in his throwing hand, requiring surgery and ending his season. 

Smith and the Bears were optimistic that Cutler could return for the playoffs. Instead, the bottom fell out in increasingly more painful ways.

The Bears went back to Hanie as Cutler’s backup and his first three starts, all losses, featured: A 25-20 loss to the Oakland Raiders where kicker Sebastian Janikowski hit six field goals, a 10-3 loss to the Kansas City Chiefs where the game’s only touchdown was via a Hail Mary by Chiefs quarterback Tyler Palko to end the first half, and a 13-10 loss to the Denver Broncos in a game Chicago led 10-0 with just over two minutes to play.

Hanie’s final start of the season came in a 38-13 loss to the Seattle Seahawks, where he threw three interceptions and dropped the team to 7-7. The Bears turned to veteran Josh McCown for the season’s final two games, which the team split, ending the season at 8-8 after once being 7-3 and missing the playoffs.

If there was one thing made clear in the 2011 season, it was that the Bears needed to find a suitable backup quarterback in case Cutler got hurt. Collins couldn’t get the job done against Green Bay, and Hanie fell apart once he experienced real competition. Just as they did years prior when they brought in Griese, Chicago turned to Jason Campbell as their next backup. Campbell had made 70 career starts between Washington and the Raiders before signing with the Bears and was just 31 years old.

The other big move the Bears made in the offseason was trading a pair of third-round picks for wide receiver Brandon Marshall. Marshall had previously played with Cutler in Denver, and the pair developed great chemistry there.

The Bears did not need Campbell to do much in 2012. Cutler started 15 of the team’s 16 games, and he had an OK year, throwing for over 3,000 yards and 19 touchdowns, but had 14 interceptions.

Marshall and Cutler still had incredible chemistry, though. The wide receiver hauled in a single-season franchise record 1,508 receiving yards, and his 11 touchdowns made him the first Bears receiver since Curtis Conway had 12 in 1995.

However, former Vikings head coach Mike Tice’s promotion from offensive line coach to offensive coordinator stunted the rest of the offense. The Bears got off to a 7-1 start before going 3-5 over their final eight games to finish the season at 10-6. Usually, a 10-6 record would be enough to get you in the playoffs, but the Bears were one of seven 10+ win teams in the NFC, and they lost the tiebreaker to the Minnesota Vikings for the final Wild Card spot.

Smith was fired at the end of the season, bringing his Bears career to a close with an 81-63 record and three playoff appearances.

To replace Smith, the Bears finally turned to an offensive-minded head coach, hiring Marc Trestman, the head coach of the CFL’s Montreal Alouettes. Trestman was seen as a “QB guru” of sorts, improving Jake Plummer and Rich Gannon in his previous NFL offensive coordinator stops with the Cardinals and Raiders. The idea was he could revolutionize Cutler and the Bears offense.

The offense was not the problem for the 2013 Bears, to his credit. In addition to Marshall putting up another great year, the emergence of second-year wide receiver Alshon Jeffrey as a perfect compliment to Marshall played a huge role. Jeffrey’s 1,421 receiving yards were second-best in a single season in franchise history, trailing just Marshall’s 2012.

Marshall still excelled, with 1,295 receiving yards and 11 touchdown receptions, making him the second player in Bears history to have double-digit touchdown receptions in multiple seasons.

Cutler likely would have finally become the first Bears quarterback to throw more than 30 touchdown passes in a single season if not for a groin injury costing him five games of the season. In 11 games, Cutler threw for 2,621 yards and 19 touchdown passes to 12 interceptions.

McCown, who had re-joined the team as Cutler’s backup, started the five games Cutler missed and went 3-2 as the starter. Remarkably, McCown turned into one of the best quarterbacks in the NFL in his five games of action, throwing for 1,829 yards, 13 touchdowns, and just one interception, leading to a bit of controversy when Cutler returned from injury and regained the starting job.

For as good as the Bears’ offense was in 2013, that’s how bad the defense was. Defensive coordinator Mel Tucker’s first season was a disaster, with Chicago’s defense placing dead last in both yards and points allowed, with the rush defense being terrible. The days of the ferocious defense and sputtering offense that past Bears teams had vanished, but it overcorrected itself in such a big way that the team went 8-8.

Their final two losses of the season came in a pair of win-and-in games, first losing 54-11 to the Philadelphia Eagles on Sunday Night Football, then losing 33-28 in a heartbreaking season finale to the Packers that featured Aaron Rodgers throwing a go-ahead 48-yard touchdown to Randall Cobb on 4th-and-8 with less than a minute to play. 

It didn’t take long for the rest of the NFL to realize that if you can contain the Bears’ offense, you’ll be able to score at will against their defense. The 2014 season wound up being a glaring example of this. Cutler was all over the place in the 5-11 season. He threw for 3,812 yards and 28 touchdowns, both second-best in franchise history. He also threw an NFL-worst 18 interceptions.

Tucker’s defense, though, was still a problem. It was most evident midway through the season when the Bears lost 51-27 to the Patriots to fall to 3-5 going into the bye week. They returned from the bye week by losing 55-21 to the Packers. By that point, even just a season and a half into his coaching tenure, it was clear things wouldn’t work out for Trestman.

After the 2014 season, Trestman was fired, as was general manager Phil Emery. Ryan Pace replaced Emery, becoming the youngest GM in the NFL at just 37 years old. He hired John Fox, who parted ways with Denver after four seasons, each featuring a playoff appearance. Fox brought Adam Gase and Vic Fangio in as his coordinators, the latter of whom was vital in attempting to rebuild the defense after years of success under Harbaugh with the 49ers.

Pace also traded Marshall to the New York Jets early in the offseason and decided to stick with Cutler, who was 32 years old, instead of starting over with a new quarterback in the draft.

After the Bears traded Marshall, they used the seventh pick in the 2015 NFL Draft to select West Virginia wide receiver Kevin White, presumably to pair with Jeffrey for the immediate future. Marred by injuries, White would wind up playing just 14 games for the Bears over the next three seasons after missing all of 2015. 

Despite a 6-10 record, both the offense and defense wound up closer to the middle of the pack in the league instead of one being in the top five and one being in the bottom five, as was the case in both of Trestman’s seasons. Cutler stayed healthy and had another strong year, 3,659 passing yards, 21 touchdowns, and 11 interceptions.

After a three-game losing streak in December, Fox benched Cutler for Jimmy Clausen, but Cutler returned and started the season’s final game after Clausen suffered a concussion. The first year under Fox was an improvement over Trestman’s last year, but there was still work to be done. Unfortunately, 2016 would prove to be another step back.

The mid-2010s were an exciting time for Chicago sports. The Chicago Blackhawks had just won their third Stanley Cup in six seasons in 2015, and the Chicago Cubs finally had their tanking efforts pay off. Their young elite prospects were ready, leading them to three straight NLCS appearances, a pennant, and a World Series victory. 

Then you had the Bears. After just one season as offensive coordinator, Gase departed to take the Miami Dolphins head coaching job, leading to Dowell Loggains being promoted from quarterbacks coach to offensive coordinator.

The offense was a disaster, whether Fox, Loggains, Cutler or a mix of all three were to blame. Cutler played just five games, and a thumb and shoulder injury limited his availability throughout the season.

He went 1-4 in those five games, threw five interceptions, and was sacked 17 times. Of the 11 games Cutler didn’t start, five went to Brian Hoyer, who threw for 1,445 yards, six touchdowns, no interceptions, and took just four sacks in five games before breaking his arm and missing the rest of the season.

The other six games went to former USC quarterback Matt Barkley, who had just 50 NFL pass attempts in his career coming into the season. Barkley struggled, particularly with turnovers, throwing for 1,611 yards, eight touchdowns, and 14 interceptions. The Bears went 3-13 on the season and each quarterback won just one game.

On March 9, 2017, the Bears released Cutler, ending his eight-season run with the team. He remains the franchise leader in passing yards (23,433) and touchdowns (154). He also dubiously leads the team in sacks taken, with a likely unbreakable 259 sacks over his eight seasons in Chicago. In 102 starts with the Bears, Cutler went 51-51. He would briefly retire, then unretire to reunite with Gase in Miami after Ryan Tannehill got injured in training camp, playing one season and then retiring again.

With the third overall pick in the upcoming NFL Draft and Cutler in the rearview mirror, the Bears again had a chance to find a franchise quarterback. Unfortunately, they’d screw it up again. Only this time, it was significantly worse than before.

Mitchell Trubisky, Mike Glennon, Nick Foles


Understandably, the Bears didn’t want to move on from Fox and Pace yet. While neither had proven to be particularly effective, they were just two years into the job, and it wasn’t Trestman-level bad. The Bears were terrible under Fox but weren’t regularly getting blown out.

With the benefit of hindsight, it’s apparent that retaining Fox and Pace for the 2017 season set the franchise back significantly. 

Shortly after releasing Cutler, the Bears signed Mike Glennon, who showed promise as a rookie in 2013 but was ultimately replaced by Josh McCown the following year. Tampa ultimately went 2-14 in that 2014 season and drafted Jameis Winston. The promise Glennon showed in his rookie season led to the Bears giving him $45 million over three years in 2017.

The idea was that they’d be drafting a quarterback, and Glennon could serve as a stopgap until the quarterback was ready, then transition to a backup role.

Everything was going according to plan. The Bears even traded up from No. 3 to No. 2, sending their third and fourth-round picks to San Francisco to move up and ensure they’d get whichever quarterback they wanted. Would they go with Deshaun Watson, the Heisman Trophy winner from Clemson? How about Patrick Mahomes, the Texas Tech standout who led the nation in passing yards in 2016? Or maybe Mitchell Trubisky, the one-year starter at North Carolina?

Of course, you know by now that they took Trubisky, a questionable pick at the time that has aged as well as a gallon of milk in the middle of the desert and continues to get worse with each Mahomes Super Bowl victory and MVP award. 

So, the Bears had their quarterbacks in place. Glennon would be the starter going into the season, and then Trubisky would take over when Fox and the coaching staff felt he was ready. Glennon started the first four games, going 1-3, and threw for 833 yards, four touchdowns, five interceptions, and lost three fumbles.

By Week 5, Fox had seen enough and named Trubisky the starter. The Bears played it very safe with Trubisky, letting him use the rest of the season to get his feet wet and get familiar with the NFL. Trubisky and the Bears went just 4-8 over the final 12 weeks to finish 5-11, and the rookie quarterback mainly was fine. He threw for 2,193 yards and seven touchdowns, along with seven interceptions.

After the season, Pace corrected his mistake from the previous offseason and fired Fox and replaced him with Andy Reid disciple and Kansas City Chiefs offensive coordinator, Matt Nagy.

Nagy was just 39 years old when he was hired, continuing the trend of NFL head coaches skewing younger than ever. The offensive-minded head coach also retained Fangio, who was pivotal for the defense. Pace improved the defense quickly shortly before the season started, acquiring former Defensive Player of the Year Khalil Mack from the Raiders for a pair of first-round picks and immediately signing Mack to a six-year contract extension.

Heading into the year looking strong on defense, it fell on Nagy and Trubisky to get the offense moving in the right direction. 

To their credit, they did! After a season-opening loss to the Packers, the Bears won three in a row heading into the bye week. The third win was a 48-10 defeat of the Bucs at Soldier Field. Trubisky threw six touchdowns in the game, finishing just one shy of Sid Luckman’s franchise record of seven. Trubisky kept rolling through the season. Despite a shoulder injury that cost him two games in November, leading to career backup Chase Daniel to be thrust into the starting role for two games, which the Bears split.

By the end of the season, the Bears boasted a 12-4 record, and Trubisky threw for 3,223 yards, 24 touchdowns, and 12 interceptions. The yardage made for the seventh-best season in franchise history, while the touchdowns were fifth-best.

Trubisky threw for a franchise playoff record 303 yards in the Wild Card Round against the Eagles. Still, the Bears would go on to lose in heartbreaking fashion when a potential game-winning field goal by kicker Cody Parkey hit off of the upright and crossbar before falling into the end zone.

The theme of the Bears rarely finding success in back-to-back years once again emerged in 2019 when the team went 8-8 and failed to make the playoffs. Trubisky took a step back, throwing for 3,138 yards and 17 touchdowns to 10 interceptions, and overall, the offense had problems executing, scoring 21 points or fewer in 12 of the 16 games. The team went 8-8 and finished third in the NFC North.

After the season, the Bears fired offensive coordinator Mark Helfrich, the former Oregon Ducks head coach, despite Helfrich not having playcalling duties. Former Dolphins and Bengals offensive coordinator Bill Lazor was hired as Helfrich’s replacement, and seemingly unconvinced that Trubisky was the guy after his stilted 2019 performance, the Bears traded for former Super Bowl MVP Nick Foles, leading to an open competition. 

In May, the competition was heated up when the Bears declined Trubisky’s fifth-year option, meaning he would be a free agent at the end of the season. A lot was on the line for the quarterback, who won the starting job out of training camp.

Trubisky started the first three games of the year, and they were each very weird.

The season opener saw the Bears pull off a 21-point fourth-quarter comeback to defeat the Detroit Lions, 27-23, behind three Trubisky touchdown passes. Week 2 saw the team get out to a 17-0 halftime lead on the New York Giants and, instead of adding to it, sat on it and played not to lose, resulting in a narrow 17-13 win that ended with an incompletion from Giants quarterback Daniel Jones to wide receiver Golden Tate from the Bears’ 10-yard line as time expired.

The Bears’ Week 3 win over the Atlanta Falcons was perhaps the most bizarre. An uninspiring first half combined with a 26-10 deficit led to Nagy pulling Trubisky for Foles midway through the third quarter. Foles rallied the team with three fourth-quarter touchdown passes, just like Trubisky two weeks earlier against Detroit. The Bears ended with a 30-26 win, and Foles was named the starter.

Foles started the next seven games for the Bears, going 2-5 and throwing for 1,852 yards, seven touchdowns, and seven interceptions before suffering a hip injury in the team’s Week 10 loss to the Vikings, leaving Nagy with no choice but to hand the keys back over to Trubisky, who would play some of the best football of his Bears career down the stretch, shaking off a pair of losses to fire off three straight wins to get the team to 8-7.

Despite losing their season finale, 8-8 was good enough for the Bears to capture a Wild Card, which brought them to New Orleans for a meeting with the Saints. Bears fans will likely remember the 21-9 loss for two things. Firstly, it was the first NFL game to be broadcast on Nickelodeon, and Trubisky was named the Nickelodeon Valuable Player (NVP) in the loss, joining his 2018 Pro Bowl appearance as the two accolades he attained in a Bears uniform.

The other thing the game will be remembered for was late in the first quarter when Trubisky threw perhaps the best pass of his career, a 50-yard strike to Javon Wims that would have tied the game and possibly given the Bears some momentum had Wims, who beat the defender by multiple steps, didn’t let the ball bounce off his hands and fall to the turf. Trubisky’s Bears career came to a close after four seasons. 

Trubisky signed with the Bills shortly after the offseason began, bringing his Bears career to a close after four seasons. He went 29-21 in 50 starts for the team, totaling 10,609 yards, 64 touchdowns, and 37 interceptions. The Bears were again in a position where they needed to acquire a quarterback. After trying and failing to pry Russell Wilson away from the Seattle Seahawks, it became clear that the Bears would be drafting one. 

Pace drafted Trubisky and it didn’t work out. Surely, they wouldn’t let him draft another quarterback, right?


Justin Fields, Andy Dalton, Tyson Bagent


Justin Fields was supposed to change everything. 

When the Bears traded up from the No. 20 to No. 11, sending multiple picks, including their 2022 first-rounder, to the New York Giants to select the former Ohio State standout, the reaction from the fanbase was resoundingly positive. The Bears signed Andy Dalton in the offseason to do something similar to what they did with Glennon and Trubisky.

Dalton started the first game, a 34-14 loss to the Los Angeles Rams, though the Bears ran a package for Fields in that game, resulting in the quarterback’s first career touchdown, a five-yard rushing score. Dalton got hurt in the next game, and it was suddenly time to go full speed ahead with Fields.

The rookie quarterback was welcomed to the NFL immediately, losing 26-6 to the Cleveland Browns in his first career start and being sacked nine times. He went just 6-for-20 as Cleveland’s vaunted defense applied pressure on nearly every play. The Bears made sure to ease Fields into the NFL, almost to a fault. They didn’t ask the rookie quarterback to do too much, but it nearly came off as them coddling him. He would remain the starter until a rib injury in Week 11 against the Baltimore Ravens.

Dalton replaced him for two weeks before Fields was healed up and ready to play, but an ankle injury and positive COVID-19 test saw him appear in just two more games during his rookie season. Fields ended the year having started ten games for the 4-9 Bears, throwing for 1,870 yards, seven touchdowns, and ten interceptions. He added 420 rushing yards and a pair of touchdowns.

After the season, both Nagy and Pace were fired, once again leading many to wonder why Pace was able to draft another quarterback as a lame-duck general manager with a lame-duck head coach. They were replaced by Matt Eberflus, a defensive-minded head coach after the offensive-minded Nagy didn’t work out, and Ryan Poles, who had spent the past 15 years in the Chiefs’ front office. 

With Dalton out of the picture for the 2022 season, it was clear that Fields would be the definitive starter. His first season under Eberflus was bizarre.

Fields started 15 of Chicago’s 17 games but threw for just 2,242 yards and 17 touchdowns. Fields, however, was unleashed as a running quarterback, and his 1,143 rushing yards were second-most by a quarterback in NFL history, trailing just Lamar Jackson’s 1,206 yards in 2019. He also broke Michael Vick’s single-game record when he rushed for 178 yards in Chicago’s Week 10 loss to the Detroit Lions. The Bears went 3-14 on the season and wound up with the first overall pick in the 2023 NFL Draft.

Poles, seemingly not enamored with any quarterback in the 2023 draft, plus having three more seasons of Fields under team control, decided to trade the first overall pick to Carolina, resulting in what could go down as one of the most lopsided trades in NFL history.

Carolina received the first overall pick, which they used to draft quarterback Bryce Young, and sent the Bears two first-round picks, the second of which was their 2024 pick, which wound up being first overall and allowed the Bears to select Caleb Williams, along with wide receiver D.J. Moore (who Poles signed to a long-term extension after acquiring) and their 2023 and 2025 second-round picks. 

Fields’ third season would be make or break for the quarterback. He had proven himself as a runner but not yet as a passer. Moore was brought in to be the missing piece and help Fields break through. To Moore’s credit, he did just that, racking up a career-high 1,364 receiving yards and eight touchdowns. 

The Bears lost their first four games of the season, as the defense gave up an average of 34 points per game in the losses.

Fields came alive in the fourth of the four losses, a 31-28 loss to the Broncos where the defense blew a big lead. Fields threw four touchdowns in the game and went 28-for-35, completing 80% of his passes. He followed it up with another four-touchdown performance, securing the team’s first win of the season with a 40-20 beatdown of the Washington Commanders. Three of the four touchdowns went to Moore, and it seemed like things were finally clicking.

Then, in the next game, a 19-13 loss to the Vikings, Fields dislocated his thumb and shoulder, putting him on the shelf until Week 11, and saw undrafted free agent Tyler Bagent start for a month, leading the team to a pair of wins but throwing six interceptions and just three touchdowns. By the time Fields returned, the Bears were 3-8 and unlikely to be playoff-bound.

They finished the year 7-10, and Fields ended his third season with a career-high in passing yards (2,562) and a career-low in interceptions with nine. He also finished with 16 touchdown passes so that he would have set a new career-high in touchdown passes had he not missed a month of action.

If the Bears didn’t have the first overall pick, they would likely have run it back with Fields, maybe drafting him another receiver or more offensive line help. Instead, Carolina was the worst team in the league, making Williams available for the Bears, and in March, they traded Fields to the Steelers for a late-round pick. 

Did the Bears give Fields a roster and coaching staff that he needed to succeed? Arguably not. Before getting Moore, the wide receiving options were thin, and the offensive line constantly needed help. But did Fields contribute to the struggles on his own? Of course. He regularly held the ball too long and made bad decisions. There will be plenty of blame to go around, especially if he figures it out with the Steelers.

Caleb Williams


Caleb Williams has a chance to change everything. The 2022 Heisman Trophy winner checked all the boxes in his college career to make him a worthy first-overall pick. As noted plenty of times throughout this writing, the Bears have had plenty of opportunities to draft a quarterback and drafted the wrong one.

The beauty of having the first overall pick is that you have your choice. It was clear early on Williams would be their guy, leading other quarterbacks in the draft, like Drake Maye, Jayden Daniels, and J.J. McCarthy, to be lumped together as a slightly lower tier than Williams.

It’s impossible to gauge if Williams will be the right pick, but he’s certainly the right pick right now. He’s walking into an offense that features Moore, fellow 2024 first-round pick Rome Odunze, Keenan Allen, D’Andre Swift, Cole Kmet, and plenty of other talents. Defensively, the Bears have looked strong, too, and they’ll be playing a last-place schedule in Williams’ rookie season. 

The pieces are all there. It’s up to Williams and Eberflus to put them together and keep them together for as long as possible. It’s been a long time since Super Bowl XX. The fanbase is desperate not only for another Super Bowl but for a sustained period of success. 

Welcome to Chicago, Caleb.