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.

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. Rounding out the offense is the offensive line, a group led by one of the best centers in NFL history.

Offensive tackleJames “Big Cat” WilliamsJohn TaitCharles Leno

Offensive tackle hasn’t exactly been a position of strength for the Bears over the last 25 years, but they have had some studs put together stellar seasons, beginning with James “Big Cat” Williams, a player who didn’t even begin his NFL career as an offensive tackle. Though the majority of his career took place in the 1990s, Williams ended his Bears tenure strong at the turn of the century. He helped pave the way for running back Anthony Thomas in 2001, earning Pro Bowl and Second-Team All-Pro honors as the Bears captured a division title.

A few years following Williams’ retirement, the Bears had big holes to fill at both tackle spots. They took a big swing to fill one of them with John Tait, and the move paid off. Chicago signed Tait to a six-year deal in 2004 away from the Kansas City Chiefs, and he immediately provided stability up front. Tait played both sides on the line but primarily lined up at left tackle. He played in 73 games across five seasons and was a critical piece of the 2006 Super Bowl team that featured a powerful rushing attack. Though he never received any Pro Bowl accolades, Tait was one of the best and most important signings of the Jerry Angelo era.

In the 2010s, the Bears found a gem in the seventh round of the 2014 NFL Draft when they selected Charles Leno Jr. out of Boise State. What seemed to be a borderline practice squad player turned into a reliable starting left tackle within just one season. Leno took hold of the left tackle job in Week 4 of the 2015 season and never missed a start for the rest of his Bears career. While Leno earned a Pro Bowl nod in 2018, he was never a star protector in the league. Still, the Bears had a revolving door at left tackle for a long time, and Leno was the solution.

Honorable mention: Fred Miller

Offensive guardKyle LongRoberto GarzaRuben Brown

In 2013, then-general manager Phil Emery shocked Bears fans by selecting a 25-year-old guard with their first-round pick. It turned out to be a great decision. Kyle Long became the Bears’ best lineman in the 2010s as he settled into the right guard position, starting as a rookie. Long quickly became one of the league’s best young offensive linemen, earning Pro Bowl nods in each of his first three seasons. He was a stud on the interior, and while he and the Bears experimented with him playing right tackle, guard was his best spot. Unfortunately, injuries took their toll, and Long’s career didn’t last as long as expected, but his prime was the best we have seen from a Bears guard this century.

While Long was a successful draft pick, these next two players were successful veteran signings. The Bears took a flyer on Roberto Garza, who signed a one-year deal in 2005 as a backup offensive lineman and potential stopgap. His stint wound up being a decade, as Garza’s solid play and versatility were a welcome addition in Chicago. Garza primarily played right guard in the 2000s but filled in on the left side as well. He was a key member of three playoff squads and wound up taking over at center following Olin Kreutz’s departure after the Bears couldn’t find a suitable outside replacement. Garza was a consummate pro and a team leader, something they needed during that time.

Prior to finding Garza, the Bears made a bigger splash with Ruben Brown, one of the best guards from the 1990s and someone who still had enough gas left in the tank during the 2000s when he signed a three-year deal. Brown made eight straight Pro Bowls with the Buffalo Bills and signed in Chicago in 2004. Though injuries limited him to just 45 games over four years, Brown was dominant when healthy and made the Pro Bowl in 2006 during his healthiest season in Chicago.

Honorable mention: Chris Villarrial

CenterOlin KreutzCody Whitehair

There is no debate as to who the Bears’ best center of the last 25 years has been. Olin Kreutz was the heart and soul of the team for the vast majority of his career. His leadership and stellar play were a key reason why Chicago became a winning franchise in the mid-2000s. Kreutz anchored the interior of the line for all four of the Bears’ playoff appearances in the 2000s, earning First-Team All-Pro honors twice in 2005 and 2006, and making the Pro Bowl six years in a row from 2001 through 2006. He was also named to the NFL’s 2000s All-Decade Team. Kreutz was arguably the best and most important player on offense since the turn of the century.

Though there’s a sizeable gap between Kreutz and the next-best center, the Bears found a good one when they drafted Cody Whitehair in 2016. Whitehair wound up filling it at center due to injuries and became a fixture at the position. While he also played guard in the back half of his career, Whitehair started at center in every game for his first three years, earning Pro Bowl honors in 2018. Whitehair did everything that was asked of him and did it well. He, like Leno, wasn’t a star player on the line, but he brought consistency and reliability.

Honorable mention: Roberto Garza

Bears All-Quarter Century Team

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