How Many Super Bowls Would Ditka’s Bears Have Won with Jay Cutler?

Chicago Bears (Photo by Stacy Revere/Getty Images)
Chicago Bears (Photo by Stacy Revere/Getty Images) /

Dan Hampton says the Chicago Bears would have won four Super Bowls in the 1980s with Jay Cutler at QB. Is he right?

Dan Hampton made some news last weekend when he told the Pro Football Hall of Fame that he and his teammates would have 4 Super Bowl titles if Jay Cutler was the quarterback of those Chicago Bears’ teams.

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You can understand where Hampton is coming from. Despite amazing teams, the QB play in Chicago was not good in those years. Jim McMahon was a very capable quarterback and made some big plays when the game was on the line, but his health was always problematic and because of that, the Bears constantly had guys like Steve Fuller, Mike Tomczak, and Doug Flutie trying to win critical games.

Hampton says Cutler would have helped the team win three more Super Bowls. Is he right? It’s, of course, impossible to know, but let’s re-examine those teams from 1984 to 1991 and see just how much of an impact Jay Cutler could have had on the roster.


The 1984 Bears went 10-6, won the division and knocked off the Washington Redskins on the way to the NFC Championship game. In that game, they squared off against the 15-1 San Francisco 49ers. McMahon only played in 9 games and the Bears went 7-2 in those games. Despite the great record, even if Cutler had an impact on the regular season, he wouldn’t have had enough of an impact to catch the 49ers. With or without Cutler, the Bears win the division and head to San Francisco in the NFC title game.

The 1984 49ers are one of the great teams of all-time. They dispatched the Bears 23-0 in that game. The Bears hung in early and only trailed 6-0. McMahon was injured and Steve Fuller was forced to play in that game and was largely ineffective. If Cutler plays in that game, this game is certainly closer, but can you claim the presence of Cutler would have closed the gap enough to have the Bears go into San Francisco and defeat this team? That answer is no. Cutler could not make a difference with the ’84 Bears.

26 Jan 1986: Quarterback Tony Eason
26 Jan 1986: Quarterback Tony Eason /


Obviously, the ’85 team is arguably the greatest single season team of all-time and that wouldn’t change with Cutler. The question is, could this team have gone undefeated with Cutler? That’s a question that would be fun to debate, but the biggest problem with the loss to the Miami Dolphins wasn’t the offense, but the defense. The game slipped away in the second quarter with a 21-3 Dolphins advantage. The Bears offense couldn’t get much going that quarter, and perhaps Cutler might have cut a touchdown off the board with some more sustained drives, but it’s hard to imagine Cutler’s impact causing enough change to change the impact of this game.

The defense wouldn’t change their game plan and Dan Marino was able to move the ball at will. That was the issue with this game. Cutler’s presence wouldn’t have been enough. The Bears still lose this game, but do indeed go 15-1 and win Super Bowl XX.


The ’86 season is the one that should cause the most debate. The ’86 New York Giants are also considered one of the best teams in NFL history, but what would the 1986 Bears be considered with an actual quarterback? The Bears went 14-2 that year. McMahon only started 6 games, and to be honest, wasn’t great in those games. Cutler definitely would have had an impact on this season. The first impact would have been on Monday Night Football on November 3 when the Bears dropped a home game to the Rams 20-17. Fuller and Tomczak were a combined 11-27 for 130 yards with no TDs and 2 INTs. Cutler almost certainly changes the outcome of that game.

Chicago Bears
Chicago Bears /

Chicago Bears

A win against the Rams raises the Bears record to 15-1. The reason that becomes critical is that the Bears would now have home field advantage throughout the NFC playoffs. Everyone knows the Bears loss to the Washington Redskins in the divisional round was due to quarterback play. Not only would the Bears be in better shape at QB, but they would be playing a less than stellar 49ers team that the Giants dispatched 49-3. You’d have to think the Bears would handle them in a similar fashion. That means the Bears would face off against the Giants in the NFC championship game, but in Chicago, not New York.

While this would have the makings of a classic contest between what would be two all-time great teams (the ’86 Bears were better statistically on defense than the ’85 squad), with the game now in Chicago, the Bears prevail and wouldn’t have had any issues dispatching the Denver Broncos. Jay Cutler wins his second consecutive Super Bowl.


The ’87 Bears would have entered the season as the favorites to win their third straight Super Bowl. The hype around this team would have been massive. Also worth mentioning, this season got butchered in the middle of the season by the strike and the scab players. With so many distractions and issues outside of the Bears control, just how much impact would it have had?

The Bears first loss was a scab player loss, and the other three losses they had on the season were more about defensive lapses than offensive struggles. Perhaps Cutler would have helped the Bears to one more regular season victory, but overall, that is largely irrelevant.

The Bears lost to the Redskins in the divisional round 21-17. McMahon played but was lousy, throwing three interceptions. Would Cutler have pushed the Bears to a victory? The team was not nearly as good as they were the two previous seasons, but if Cutler makes enough of an impact to win this game, the Bears almost certainly beat the Minnesota Vikings at home in the NFC Championship game and would again beat an over-matched Denver Broncos team that overachieved under John Elway.

For the sake of argument, we will give the nod to Cutler and the Bears now become a historic franchise, becoming the only team to win three consecutive Super Bowls.


The 1988 Bears, despite not having a quarterback, managed to go 12-4 earning the best record in the NFC. The Bears dispatched the Philadelphia Eagles in the Fog Bowl before falling to the 49ers 28-3 in Chicago in the NFC Championship game.

The 49ers set the pace early in that game with two touchdowns to Jerry Rice. Montana had the defense’s number that game, throwing for nearly 300 yards and three touchdowns. Knowing how the Bears fell behind early and never could catch up. Cutler certainly would have given the Bears the passing attack to try and get back in the game, but this isn’t coming back against a random team. This was Bill Walsh’s 49ers. Hard to imagine that even Cutler would have changed the outcome of that game.

The Bears historic run ends, the 49ers go on to win the Super Bowl and end the Bears drive for a fourth consecutive title.


The ’89 season was not pretty for Chicago. The Bears offense actually outranked the defense that season. After a 4-0 start, the Bears derailed and lost 10 of their last 12. Cutler’s presence might have pushed the Bears to 8-8, but nothing was going to save this season, not even Joe Montana. There’s not much to say about this except, let’s come back and try again next season.


The Bears rebounded after a rough 1989 season to go 11-5 and win the division. The 49ers went 14-2 and the Giants went 13-3, even with Cutler, the Bears still wouldn’t have managed to avoid the wild card. In the divisional round, the Bears were squashed by the New York Giants 31-3. The Giants completely shutdown the Bears offense that game and the Giants did what they wanted offensively. Cutler or not, nothing changes here.

The writing is on the wall. Only a few of the Bears remain from the dominant teams in the mid 80s. The Bears are now three years removed from their last Super Bowl. The Bears should probably start rebuilding, but they’ll hold out for one more run in 1991.

Jan 26, 1992: Quarterback Mark Rypien of the Washington Redskins holds his daughter after Super Bowl XXVI against the Buffalo Bills at the Hubert Humphrey Metrodome in Minneapolis, Minnesota. The Redskins defeated the Bills 37-24. Mandatory Credit: Rick Ste
Jan 26, 1992: Quarterback Mark Rypien of the Washington Redskins holds his daughter after Super Bowl XXVI against the Buffalo Bills at the Hubert Humphrey Metrodome in Minneapolis, Minnesota. The Redskins defeated the Bills 37-24. Mandatory Credit: Rick Ste /


The defense recovered in 1991. Despite being a long way from the mid 80s dominance, they were still one of the top 5 defensive units in the NFL. The team finished 11-5 but had a couple losses that were due to a lack of offense. Is it impossible to believe a Cutler led offense could have pushed the record to 12-4? If that’s the case, this season potentially could change.

If the Bears win one more game, they would have won the division based on best conference record for the tiebreaker against the Detroit Lions. The Bears would have earned a first round bye and most likely easily dispatched a young Dallas Cowboys team not quite ready for primetime. Sure, the Bears lost to the Cowboys this season in the wild card round, but they lost 17-13 and lost the turnover battle 3-0 thanks to a dreadful Jim Harbaugh performance (2 INTs, 1 fumble lost). With a better QB, this game has a different outcome.

That would put the Bears in the NFC Championship game on the road against a great Washington Redskins team. With the Bears not nearly what they were a few years earlier, it’s hard to make the case for the Bears to go into Washington and defeat a 14-2 squad that dominated opponents much of the year. The Bears would fall to the Redskins and end their run of greatness once and for all.

Wrap Up

Is Dan Hampton right, would the Bears have won 4 Super Bowls? That’s hard to imagine. It’s very tough to make the case that better QB play would have helped the team win Super Bowls in 1984, 1989, 1990 or 1991. That means Hampton is arguing that the Bears would have won 4 straight championships. As it turns out, that’s close to an impossibility in professional sports, especially in football where injuries are unpredictable and play such a prominent role in games.

However, there’s no question that better quarterback play could have greatly impacted the Bears. The Bears arguably would have won three Super Bowls and been in the NFC Championship another three times. That’s a ridiculous stretch over 8 years. That’s the type of stretch that would be argued as one of the great dynasties in NFL history.

I will say, the 1987 Super Bowl title that the Bears ‘won’ with Cutler is a questionable one. That team was definitely not as strong as the ’85 or ’86 squads and you could argue the ’88 squad was better. It could definitely be argued that the Bears wouldn’t have won in ’87, but despite the greatness of the ’86 New York Giants, it is a very strong likelihood that the Bears win in 1986.

Four Super Bowls with Cutler? Definitely not, but the argument can be had for 3, and it’s hard to imagine that Cutler wouldn’t have gotten the Bears over the hump and won at least one more title and fortified the greatness of the 80s Chicago Bears.