Bears All-Quarter Century Team: Quarterbacks

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Twenty-five years of Chicago Bears football are in the books since the turn of the century. Since the calendar turned over to 2000, the Bears have seen some success, but also plenty of woeful stretches. Early on, Chicago became a defensive force, claiming four division titles and reaching only their second Super Bowl in franchise history from 2000 to 2010. Since then, however, a 14-year playoff victory drought that is still ongoing and a one-sided fight with their rival Green Bay Packers have taken the spotlight.
For all the ups and downs the Bears have seen, however, they had plenty of talent over the years across offense and defense. Multiple former Bears players are already in the Hall of Fame, while many more provided years of incredible play in the navy and orange.
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Here at Bears Wire, we're celebrating the best Bears players at each position over the last 25 years. We're going position by position to name the Bears' All-Quarter Century Team for those who played from 2000 through 2024. Up first are quarterbacks, a position that the Bears have historically struggled to develop but still had stretches of productivity.
Jay Cutler
2009 - 2016
23,443 passing yards, 154 passing touchdowns, 109 interceptions, 85.2 passer rating; 6 rushing touchdowns
CHICAGO, IL - OCTOBER 31: Jay Cutler #6 of the Chicago Bears looks to throw a pass during the first half against the Minnesota Vikings at Soldier Field on October 31, 2016 in Chicago, Illinois. (Photo by)
It's no secret that the quarterback position has been a liability for the Bears over the last 25 years. Even as the league has shifted to more of a passing focus, the Bears are still the only team without a 4,000-yard passer. They got close a couple times with Jay Cutler, though, who holds the team record for most passing yards (23,443) and touchdowns (154) in franchise history.
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Cutler never reached the heights many believed he would when the Bears landed him in a blockbuster trade with the Denver Broncos in 2009. He had stretches of brilliance thanks to his rocket arm and above-average athleticism, but his decision-making wound up costing the Bears more often than not. Cutler has the most 3,000-yard passing seasons in Bears history with five and led Chicago to their last playoff victory during the 2010 season.
Despite his flaws, no other Bears quarterback comes close to his production over the last 25 years. Nearly 10 years after he last put on a Bears uniform, you will still find plenty of highlights circulating social media with fans marveling at Cutler's talent.
Mitchell Trubisky
2017 - 2020
10,609 passing yards, 64 passing touchdowns, 37 interceptions, 87.2 passer rating; 8 rushing touchdowns
CHICAGO, ILLINOIS - JANUARY 06: Mitchell Trubisky #10 of the Chicago Bears looks to pass against the Philadelphia Eagles in the second quarter of the NFC Wild Card Playoff game at Soldier Field on January 06, 2019 in Chicago, Illinois. (Photo by)
Behind Cutler is Mitchell Trubisky, a polarizing player, but one who stands out as the second-best passer of the last 25 years. Trubisky is the only quarterback to have led the Bears to multiple postseason berths this century and has the highest passer rating of any Bears quarterback with more than 5,000 career passing yards, with 87.2. Trubisky was never a turnover machine and had efficient games during his four seasons as the primary starter. His six-touchdown performance against the Tampa Buccaneers in 2018 still lives in Bears lore.
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Trubisky was limited in what he could do on the field, though, and never became more than an average starter at best. The former No. 2 overall pick was never as bad on the field as some made him out to be, but his flaws were magnified given the superstar play of Patrick Mahomes, whom the Bears passed up on in favor of Trubisky. With respect to Kyle Orton's ability to manage a game, Rex Grossman's postseason success, and Justin Fields' electrifying runs, Trubisky provided the most consistency at the position for an extended period of time since 2000.
Honorable mention: Caleb Williams
Bears All-Quarter Century Team
6/22: Quarterbacks
6/22: Running backs
6/23: Wide receivers
6/23: Tight ends
6/24: Offensive line
6/24: Defensive tackles
6/25: Defensive ends
6/25: Linebackers
6/26: Cornerbacks
6/26: Safeties
6/27: Specialists
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This article originally appeared on Bears Wire: Bears All-Quarter Century Team: Quarterbacks