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Chicago Bears All Quarter-Century Team: Offense Edition

Originally posted on Last Word On Sports
By Zach Jonkman | Last updated Jun 11, 2025 12:13 PM ET

The NFL has been a fascinating story in the 21st century, with a constant influx and outflow of talent throughout the league. In that time, the Chicago Bears have had varying levels of success. The high points have included some all-time level talent that has had some impact on the sport today. Which Bears from the last 25 years of franchise history would make the quarter-century offense team?

Chicago Bears All Quarter-Century Team: Offense Edition

Quarterback, Jay Cutler

Honorable Mentions: Rex Grossman, Mitchell Trubisky, Justin Fields, Caleb Williams

Jay Cutler was one of the most bipolar quarterbacks in NFL history. During his time in Chicago, he would go from leading the league in interceptions one year to leading his team to an NFC Championship game the next.

If not for some major injuries throughout his time in Chicago, he could have seen some more sustained success in the NFL. Given the Bears’ history with quarterbacks, this might be the most lackluster position on the entire team.

Running Back, Matt Forte

HM: David Montgomery, Jordan Howard, Thomas Jones

Matt Forte was the engine behind the Bears’ offense during his time in Chicago. His versatility as an offensive weapon is nearly unmatched.

Forte accumulated over 8,000 rushing yards and over 4,600 receiving yards in his time in the NFL. His dual-threat ability allowed the Bears to use him in many unique ways in the run and pass game that gave defenses fits. That doesn’t even mention his great contact balance and shiftiness to create extra yards after interacting with defenders.

Wide Receiver, Brandon Marshall and Alshon Jeffery

HM: Allen Robinson, Johnny Knox, Marty Booker, D.J. Moore

Brandon Marshall wasn’t with the Bears for very long, but his time there will certainly be remembered. He was the top receiving threat on multiple electric units in Chicago and had many signature performances in his three years on the Bears.

Alshon Jeffrey was Marshall’s main running mate at receiver, and opposing defenses have to keep an eye on him. His ability to stretch the field with his long speed and high-point catching ability allowed other contributors on the offense to succeed with less difficulty.

These two receivers shared some time in Chicago, and it made for some truly explosive fireworks on the offensive side of the ball.

Tight End, Cole Kmet

HM: Martellus Bennett, Greg Olsen, Zach Miller

In a room with lots of promising talent and narratives, Cole Kmet is the pick for the Bears’ best tight end of the last 25 years.

This choice may come off as questionable, but the numbers speak for themselves. He is first in receiving yards and receptions among tight ends, while also working with three different quarterbacks and two coaching regimes.

He isn’t a flashy pick by any means, but he’s a great security blanket that had an 85.5% catch percentage while catching all eight of his red zone targets in 2024. Kmet is a great addition to this offense.

Left Tackle, Charles Leno Jr.

HM: Braxton Jones

Unfortunately for the Bears, there haven’t been many stable left tackles in recent history for this team. Charles Leno Jr. and Braxton Jones are the two clear favorites, but Leno gets the spot because of his longer career to this point.

The two of them have been similar in terms of talent and impact, but Leno’s seven seasons and one Pro Bowl appearance with the Bears, compared to Jones’ three years and zero Pro Bowls, give him the edge.

Left Guard, Cody Whitehair

HM: Teven Jenkins, James Daniels, Josh Sitton, Joe Thuney

Cody Whitehair wasn’t an elite guard, but his versatility and consistency on the interior offensive line earned him this spot.

His Pro Bowl nod in 2018 and eight-year career with the Bears were rather impressive, given how much roster turnover they’ve had recently.

Shoutout Joe Thuney for making the honorable mentions. He hasn’t even played a snap for the Bears, but his resume alone almost snagged the starting spot.

Center, Olin Kreutz

HM: Roberto Garza, Cody Whitehair

Olin Kreutz may go down as one of the most underrated centers in NFL history. He wasn’t only a talented player, but a staple of the Chicago Bears’ offensive line in the 2000s.

Kreutz earned six straight Pro Bowl nods from 2001-2006 and even made the All-Pro First team. He also made the HOF All-2000s Team as a center.

Right Guard, Kyle Long

HM: Roberto Garza

Kyle Long is another easy choice for this offensive line spot. The Bears spent a good amount of time since Long retired trying to find a suitable replacement and will hopefully find some success soon.

Long made three Pro Bowls in the first three years of his short career, but was still a great player the rest of his time in the NFL.

Right Tackle, Darnell Wright

HM: Bobby Massie

Darnell Wright may not have been playing for long, but he’s been very good since entering the league. Wright earned an All-Rookie Team spot for his 2023 season.

He played 100% of snaps in 2023 and 95% of snaps in 2024. Now, under new coach Ben Johnson, Wright has a chance to become one of the elite tackles in the league.

This article first appeared on Last Word On Sports and was syndicated with permission.

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