Surely, based on the title alone, you get the gist of what you’re about to read here. Since we’re closing in on the end of the first quarter of the 21st century, you’ve likely been bombarded with quarter-century content over the last few months, and that won’t stop until the calendar turns from 2025 to 2026. Today, it’s time for the Chicago Bears to step into this quarter-century spotlight.
Unlike many lists of this nature, I’m not just picking players who had most exemplary playing careers for the Chicago Bears. Using a wine term — which I’m completely qualified to do since my knowledge of wine rivals Michael Scott’s — I’m picking the best vintage of each of these 53 players… a specific version to best represent the Quarter-Century Chicago Bears.
Quarterbacks (3)
Starter: Mitchell Trubisky (2018)
Backups: Jay Cutler (2010), Caleb Williams (2024)
That’s right, just like Mitch still has soft spot for the city of Chicago and the Bears organization, I still have a soft spot for him too, and that’s quite a surprise given where I was at mentally when the Bears traded up to select Trubisky with the 2nd overall pick in the 2017 NFL Draft. But to this day, I’ll maintain that Trubisky’s 2018 season was the best of any Bears quarterback of the last 25 years, and yes, the numbers do back it up.
Mitchell Trubisky, 2018 – 3,223 passing yards (sixth-most of any Bears quarterback since 2000), 24 passing touchdowns (3rd), 95.4 passer rating (best among all Bears quarterbacks with at least 300 pass attempts in a season), 421 rushing yards (second-most among all Bears quarterbacks since 2000 not named Justin Fields).
And then there’s this… when the Bears gave up the lead in the 2018 NFC Wild Card Round versus the Philadelphia Eagles, Trubisky led Chicago down the field to give the Bears a chance to win the game and advance to the Divisional Round of the Playoffs. Of course, we all know how things worked out once Cody Parkey ran onto the field, but I’ll forever appreciate the fact that Mitch did his job and got the Bears in field goal range.
Running Backs (4)
Starter: Matt Forte (2013)
Backups: Thomas Jones (2006), Tarik Cohen (2018), Anthony Thomas (2001)
Make a list of the most underrated football players of the last quarter-century, and it’s only relevant if Matt Forte is included on it. Forte never got the shine that many of his contemporaries did, but there’s a compelling case you could make that the former Tulane standout was one of the most complete running backs of his era.
Forte hauled in 102 receptions during the 2014 season, the most ever by a running back at the time, and the second-most ever by any Chicago Bear. The year prior — the Forte vintage I chose, by the way — he rushed for 1,339 yards and 9 touchdowns. The only other running back in Chicago Bears history to reach those numbers in a single season was Walter Payton, who did so six times.
Wide Receivers (6)
Starters: Brandon Marshall (2012), DJ Moore (2023), Alshon Jeffery (2013)
Backups: Allen Robinson (2020), Marty Booker (2001), Muhsin Muhammad (2006)
A surprisingly deeper pool of players than I expected to choose from, I tried my best to get unsung pass-catchers such as Johnny Knox (2010 – 51 catches, 960 yards, 5 touchdowns) or Bernard Berrian (2007 – 71 catches, 951 yards, 5 touchdowns) on the roster, but couldn’t do it with these six wideouts ahead of them. Knox was an especially hard cut. I had a soft spot for him and was irrationally upset when he suffered one of the most gruesome injuries in Bears history.
Brandon Marshall, Alshon Jeffery and DJ Moore were easy selections, and they would theoretically work quite well together on the field. Although the production wasn’t quite as prolific as you’d remember, Allen Robinson needed to be on the roster. He may have the best set of hands of any Bears receiver I’ve seen.
Marty Booker notched back to back 1,000 yard seasons when the Bears were trotting out Jim Miller and Shane Matthews at quarterback, and Muhsin Muhammad had it even worse with a Kyle Orton, Rex Grossman and Brian Griese trifecta.
Tight Ends (3)
Starter: Martellus Bennett (2014)
Backups: Greg Olsen (2009), Cole Kmet (2023)
There’s a world where the Bears never trade Greg Olsen, re-sign him at the conclusion of his rookie contract, and he becomes a three-time Pro Bowler in Chicago instead of in Carolina, and frankly, that’s a world I wish we lived in. Even still, his 2009 season was good enough to earn him a roster spot along with Martellus Bennett — whose 2014 season was the most prolific of any Bears tight end not named Mike Ditka — and Cole Kmet, whose spot on this roster and the 2025 Bears depth chart, will likely be overtaken at some point by Colston Loveland.
Offensive Line (8)
Starters: Olin Kreutz (2005), Kyle Long (2014), Cody Whitehair (2021), James Williams (2001), Charles Leno (2018)
Backups: Ruben Brown (2006), Roberto Garza (2009), John Tait (2005)
Save for Olin Kreutz, there isn’t another perennial All-Pro or potential Hall of Fame candidate on this unit, but at the very least, this group of eight is going to hold up very well against any other team’s quarter-century defensive line, and that’s all we can ask for.
Defensive Line (9)
Starters: Khalil Mack (2018), Tommie Harris (2005), Akiem Hicks (2018), Julius Peppers (2010)
Backups: Robert Quinn (2021), Montez Sweat (2023), Alex Brown (2005), Adewale Ogunleye (2007), Ted Washington (2001)
This is arguably the strength of the entire roster; a group that can absolutely wreck shop and make life a whole heck of a lot easier on our linebackers and defensive backs. The acquisition of Khalil Mack and his subsequent 2018 season remains one of the bright spots of the last quarter-century for the Bears. Robert Quinn may have notched more sacks in 2021 than Mack did in any of his years with the Bears, but Mack is the single most dominant edge rusher in modern Chicago Bears history.
As a result, the signing of Julius Peppers in 2010 has actually become underrated. Peppers was a 1st Team All-Pro in 2010, and he may have been the best player on a team that went to the NFC Championship Game that season. Tommie Harris and Akiem Hicks are bonafide game-wreckers in the middle, and we’ve got a lot of depth in this group as well.
Linebackers (5)
Starters: Brian Urlacher (2001), Lance Briggs (2009)
Backups: Roquan Smith (2021), Danny Trevathan (2018), Rosevelt Colvin (2001)
Picking out our Brian Urlacher vintage was one of the more difficult roster choices I had to make, but in the end, I went with the 2001 version — a younger, faster, and more disruptive presence who was a tackling machine, an effective pass rusher and the league’s best linebacker in pass coverage — instead of the 2005 (Defensive Player of the Year), 2006 (the should’ve been back-to-back Defensive Player of the Year) or 2010 (the last great Urlacher year) versions.
This Urlacher decision is admittedly partially selfish in nature. As a 9-year-old kid who was playing linebacker in youth football, the 2001 version of Brian Urlacher was the first guy I can remember watching with an eye on what I wanted to be as a football player.
After we get Peanut Tillman in the Hall of Fame, it’s time we start getting the train rolling full steam ahead for Lance Briggs, who along with Kreutz and Peanut is the most underrated Bears player from the Lovie Smith era. Hey, speaking of Peanut Tillman…
Cornerbacks (6)
Starters: Charles Tillman (2012), Jaylon Johnson (2023), Kyle Fuller (2018)
Backups: Tim Jennings (2012), Nathan Vasher (2005), R.W. McQuarters (2001)
10 of Peanut Tillman’s 44 career forced fumbles came during the 2012 season, and four of those came in one single game against the Tennessee Titans, highlighted in my 10 Most Memorable Bears Wins of the Quarter-Century column earlier this week. Tillman also picked off three passes, and returned all three for touchdowns during the 2012 season. Put some damn respect on the man’s name, NFL! He should be Canton-bound!
Hopefully Jaylon Johnson will someday be Canton-bound as well. He established himself as one of the league’s stickiest and most skilled cover corners in 2023 and got paid accordingly for his efforts. Although Kyle Fuller never cashed in like Jaylon Johnson did, he did lead the league in interceptions in 2018.
Safeties (4)
Starters: Eddie Jackson (2018), Mike Brown (2001)
Backups: Chris Harris (2010), Danieal Manning (2009)
I want my safety group to be aggressive and opportunistic, and in Eddie Jackson and Mike Brown, we’ve got exactly that. Brown is the only player in NFL history who has scored interception returned touchdowns in back-to-back overtime games, and Eddie Jackson may hold the unofficial record for most defensive touchdowns called back by post-pick penalties. Either way, we’re turning defense into offense rounding out our starting group with these two.
Special Teams (5)
Robbie Gould (2011), Tory Taylor (2024), Patrick Mannelly (2006), Devin Hester (2006), Cordarrelle Patterson (2020)
Solid special teams have been a Bears trademark when the Monsters of the Midway have been at their scariest in the 21st century, and with this group of special teams contributors, I have no doubt we’ll be at our best. Robbie Gould was arguably never better than he was during a forgettable 2011 season, going 28-of-32 on field goal attempts and a perfect 6-for-6 on kicks from 50+ yards out. Tory Taylor may have only been a rookie, but I gave him the nod over Brad Maynard and Pat O’Donnell.
Devin Hester will be handling kick and punt return duties, but Cordarrelle Patterson deserves some recognition for his contributions in Chicago as well. And don’t forget about long snapper Patrick Mannelly. He played in a franchise record 245 games in his career.
Chicago Bears Quarter-Century 53-Man Roster