The Greatest Chicago Bears of All Time…

The Chicago Bears are one of the most storied franchises in NFL history. Established in 1920, they have a legacy of greatness that spans over a century, defined by eight NFL Championships, one Super Bowl title, and an unmatched 34 players inducted into the Pro Football Hall of Fame. The Bears have built their identity around toughness, defense, and a culture of winning. Their rivalry with the Green Bay Packers, which dates back to the league’s earliest days, remains one of the fiercest in all of sports.

Determining the greatest Chicago Bears of all time is no small task. From the bruising players of the 1940s to the legendary 1985 Bears arguably the best team ever assembled this list showcases players who not only defined their eras but also set standards for excellence that resonate across generations. Using Pro Football Reference’s Approximate Value (AV), which quantifies a player’s overall impact on the field, alongside awards, records, and personal accolades, here’s a look at the best Bears to ever don the navy blue and burnt orange.

 

1. Walter Payton – Running Back (1975–1987)

It’s impossible to talk about the Chicago Bears without mentioning Walter Payton, affectionately known as “Sweetness.” Widely regarded as one of the greatest football players of all time, Payton combined power, speed, agility, and durability like no other.

Payton’s career highlights are staggering:

NFL MVP (1977)

Super Bowl Champion (XX)

Nine Pro Bowl Selections

Retired as the NFL’s All-Time Leading Rusher (16,726 yards)

Payton’s relentless work ethic and ability to dominate games made him the heart and soul of the franchise for over a decade. His toughness extended off the field as well, where his charity work and humility made him a beloved figure far beyond Chicago.

 

2. Dick Butkus – Linebacker (1965–1973)

Dick Butkus epitomized the “Monsters of the Midway.” As one of the fiercest linebackers in NFL history, Butkus was a relentless force on the field. Known for his devastating hits and ability to intimidate opponents, Butkus was the prototype for the modern linebacker.

In his nine-year career, Butkus was:

An Eight-Time Pro Bowl Selection

Two-Time Defensive Player of the Year (1969, 1970)

Even though the Bears struggled during his tenure, Butkus’s impact on the game and his reputation as a ferocious competitor have solidified his place in NFL lore.

3. Gale Sayers – Running Back (1965–1971)

Gale Sayers’ career was tragically cut short due to injuries, but his brilliance during his seven seasons in the league remains unmatched. Known as the “Kansas Comet,” Sayers was an electrifying playmaker who could score from anywhere on the field.

Highlights of Sayers’ legendary career include:

Four Pro Bowl Selections

Two-Time Rushing Leader (1966, 1969)

Youngest Player Inducted into the Hall of Fame (Age 34)

His rookie season in 1965 remains one of the best in history, as he scored 22 touchdowns, including an iconic six-touchdown performance in a single game against the San Francisco 49ers.

 

4. Mike Singletary – Linebacker (1981–1992)

The defensive leader of the legendary 1985 Bears, Mike Singletary embodied intensity and focus. “Samurai Mike” was the heart of the defense that allowed just 198 points during the regular season a feat still considered one of the greatest defensive performances in NFL history.

Singletary’s accolades include:

Two-Time Defensive Player of the Year (1985, 1988)

Ten-Time Pro Bowl Selection

Super Bowl XX Champion

Singletary’s sideline leadership, work ethic, and intelligence made him the anchor of arguably the best defense ever assembled.

5. Sid Luckman – Quarterback (1939–1950)

The Chicago Bears have long been associated with tough defense and strong running games, but Sid Luckman was the exception a quarterback who revolutionized the game during his era. Luckman thrived in George Halas’s T-formation offense, leading the Bears to four NFL Championships.

Career highlights include:

NFL MVP (1943)

Three-Time All-Pro Selection

Most Passing Touchdowns in a Game (7)

Luckman’s legacy as one of the first great quarterbacks in NFL history remains intact, and he’s still considered one of the best signal-callers in team history.

6. Brian Urlacher – Linebacker (2000 2012)

Brian Urlacher carried the mantle of great Bears linebackers into the modern era. As the leader of the defense during the 2000s, Urlacher was a versatile and athletic player who could stop the run, drop into coverage, and rush the passer.

Urlacher’s impressive résumé includes:

NFL Defensive Player of the Year (2005)

Eight Pro Bowl Selections

Member of the Pro Football Hall of Fame

Urlacher’s combination of physicality and athleticism made him the face of the Bears for over a decade.

7. Richard Dent – Defensive End (1983 1993, 1995)

As the dominant pass rusher on the 1985 Bears defense, Richard Dent wreaked havoc on opposing quarterbacks. His ability to pressure the passer was a key component of the Bears’ success that year, capped by his MVP performance in Super Bowl XX.

Dent’s career stats and honors include:

137.5 Career Sacks

Four-Time Pro Bowl Selection

Super Bowl XX MVP

Dent’s impact was felt far beyond the 1985 season, as he consistently delivered as one of the league’s premier edge rushers.

8. Bronko Nagurski  Fullback/Linebacker (1930–1937, 1943)

Bronko Nagurski was a two-way player whose strength and power became legendary in the early days of the NFL. A bruising fullback and a dominant linebacker, Nagurski helped lay the foundation for the Bears’ success in the 1930s.

Career highlights include:

Three NFL Championships

Inducted into the Pro Football Hall of Fame (Class of 1963)

Nagurski’s name remains synonymous with toughness, and he’s remembered as one of the sport’s earliest superstars.

9. Devin Hester – Return Specialist/Wide Receiver (2006–2013)

Devin Hester changed the way the NFL viewed special teams. As the most electrifying returner in NFL history, Hester’s ability to score every time he touched the ball was unparalleled.

Career highlights include:

NFL Record for Most Return Touchdowns (20)

Four-Time Pro Bowl Selection

Super Bowl XLI Kickoff Return Touchdown

Hester’s impact on field position and momentum made him a game-changer in an era when special teams often flew under the radar.

10. George Halas – Player Coach Owner (1920–1983)

While George Halas played only briefly, his influence on the Chicago Bears transcends the playing field. Known as “Papa Bear,” Halas was the founder, owner, and longtime coach of the team. Under his leadership, the Bears became one of the most successful franchises in NFL history.

Halas’s coaching achievements include:

Six NFL Championships

318 Career Wins as Head Coach

Without Halas, the Chicago Bears might not exist as we know them. His contributions to the team and the league as a whole are immeasurable.

Honorable Mentions

Dan Hampton: A dominant defensive lineman and a key member of the 1985 Bears.

Charles Tillman: Known for his “Peanut Punch,” Tillman was one of the best cornerbacks of his era.

Olin Kreutz: A stalwart center who anchored the offensive line for over a decade.

The Chicago Bears’ history is rich with legends, from early pioneers to modern-day stars. Their tradition of greatness, particularly on the defensive side of the ball, continues to define their identity as one of the NFL’s premier franchises. While the game has evolved over the decades, the legacies of these players remain timeless, a testament to the enduring spirit of the Chicago Bears.