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The greatest Chicago Bears of all time
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The greatest Chicago Bears of all time

One of the original NFL franchises, the Chicago Bears have been around for over a century. They've won eight NFL Championships, one Super Bowl, and sent 34 players to the Pro Football Hall of Fame, more than any other team. Their bitter rivalry with the Green Bay Packers is truly the stuff of legends. 

There will be a lot of 1985 Bears on this list, and for good reason. They're (arguably) the best team ever assembled.

This list was created by measuring each player's Approximate Value, a Pro Football Reference statistic that's used to "put a single number on the seasonal value of a player at any position from any year," according to their website. Awards, stats, and records were also considered. Let's get to it!

 
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1. Walter Payton

Walter Payton
Owen C. Shaw/Getty Images

Payton was drafted out of Jackson State and was touted as a generational running back. To put it simply, he proved the analysts right. In 1977, Payton was a one-man wrecking crew and walked away with NFL MVP for leading the league in scrimmage yards and carrying the Bears to the playoffs. After some struggles through Payton's tenure early in his career, the 1985 Bears went 15-1 thanks to their smashmouth offense and all-time great defense. They went on a dominant playoff run and beat the New England Patriots in the Super Bowl, 46-10, cementing their status as the greatest team of all time. 

Payton retired in 1987 as the NFL's all-time leading rusher, and died from bile duct cancer at the age of 46. The Walter Payton NFL Man of the Year award is named in his honor and is his lasting legacy. The highest honor a player can receive, the Walter Payton award is given to a player who excels on the field and gives back to his community off it. 

 
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2. Mike Singletary

Mike Singletary
Malcolm Emmons-USA TODAY Sports

Singletary was the motivational leader of the 1985 Bears defense. Thanks to him, the Monsters of the Midway were back and better than ever. He was passionate about the game of football and demonstrated a high football IQ and determination. In the golden era of the Bears, Singletary was calling the shots on defense. The two-time AP Defensive Player of the Year is remembered as the one of the greatest linebackers of all time. After his playing career ended, he became a coach and had an up-and-down record.

 
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3. Brian Urlacher

Brian Urlacher
Jonathan Daniel-Staff-Getty Images

The Bears have a long lineage of great linebackers throughout their 100-year history. Few were as good as Urlacher. The fact he is the second greatest Bears linebacker says a lot about the team's rich history at the position. 

Urlacher introduced himself to the NFL by winning the 2000 AP Defensive Rookie of the Year award. The eight-time Pro Bowler was a dynamic playmaker who disrupted plays on a down-by-down basis. He was the last player you'd want to get hit by.

Besides Baltimore Ravens linebacker Ray Lewis, no one was better at the position in the mid-2000s. Urlacher won the 2005 AP Defensive Player of the Year award. The following season, he led the Bears to the Super Bowl, where they lost to Peyton Manning's Indianapolis Colts. He also took the team to the 2010 NFC Championship Game, a heartbreaking loss to the Green Bay Packers, their arch nemesis. He retired in 2012 and was a first-ballot Hall of Famer. 

 
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4. Dan Hampton

Dan Hampton
Malcolm Emmons-USA TODAY Sports

A versatile defensive lineman, Hampton could play both defensive end and tackle. He earned a Pro Bowl nod at both positions. The Danimal played the game with heart and hustle. Hampton was instrumental in Buddy Ryan's 4-6 Defense because he had to be accounted for on every play and was double-teamed on a regular basis, which freed others and left them unblocked. He made the 4-6 Defense work and was one of the most intimidating players from the 1985 Bears, which is saying something. After 10 knee surgeries and 82 career sacks, Hampton called it a career in 1990.

 
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5. Lance Briggs

Lance Briggs
Dennis Wierzbicki-USA TODAY Sports

Briggs was drafted to complement Urlacher at Will Linebacker. Together, they formed a monstrous linebacker corps. The Bears defense from the 2000s was feared around the league and featured big names like Charles Tillman, Mike Brown, and many more who came and went. A member of the 2006 Bears squad that went to Super Bowl XLI, he was everything you could ask for from an outside linebacker. Injuries hampered his career and he retired in 2014.

 
6 of 25

6. Steve McMichael

Steve McMichael
Jonathan Daniel-Stringer-Getty Images

McMichael was an All-American with the Texas Longhorns in college. After burning out with the New England Patriots, the eccentric defensive lineman found a home in the Windy City. 

In Chicago, he was a vital member of the 1985 Bears. McMichael let his outgoing personality shine and was quite the character. The two-time Pro Bowler racked up 95 career sacks. After retiring from football, he became a pro wrestler with the Four Horseman stable. The edgy defensive lineman had the perfect personality for pro wrestling.

 
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7. Richard Dent

Richard Dent
RVR Photos-USA TODAY Sports

Nicknamed the Sackman for his knack at getting to the quarterback, Dent knew when to peak at the right time. He led the 1985 Bears in sacks, as well as the entire league, and was named Super Bowl MVP after wrecking havoc all game. That season was the crowning achievement of his career. 

The speedy pass rusher won another ring with the 49ers in 1994 and also played for the Colts and Eagles as a rotational player on both teams. He retired as the Bears' all-time leader in sacks and is a Hall of Famer. 

 
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8. Dıck Butkus

Dıck Butkus
Tony Tomsic-USA TODAY Sports

Butkus was a terrifying player to go up against. The linebacker was one of the hardest hitters in NFL history and struck fear into anyone who came to the Midway to play football. 

Butkus was born in Chicago, went to high school there, played college football at Illinois and played nine seasons with the Bears. A true Chicagoan! An all-time great linebacker, he's in the Hall of Fame and was named to the All-Century Team. 

 
9 of 25

9. Gary Fencik

Gary Fencik
Herb Weitman-USA TODAY Sports

A hometown kid from Chicago, Fencik played wide receiver at Yale and was drafted by the Miami Dolphins, but was cut after training camp. He came back to Chicago and was signed by the Bears. They moved him from wide receiver to safety and he thrived in the new position, earning two Pro Bowl nods. A member of the 1985 Bears, he was the hard-hitting safety of the 4-6 Defense. He retired as the Bears all-time interceptions leader and went into finance after his football career.

 
10 of 25

10. Jay Hilgenberg

Jay Hilgenberg
Manny Rubio-USA TODAY Sports

When the 1985 Bears dominated their way into the history books, Hilgenberg was at the center of it all. As the team's starting center, he paved the way for their rushing attack led by Payton. The seven-time Pro Bowler was one of the best at his position in his heyday. He also played for the Browns and Saints, becoming teammates with his brother, Joel, in New Orleans. Now, he's a renowned Chicago sports radio host. 

 
11 of 25

11. Matt Forte

Matt Forte
Dennis Wierzbicki-USA TODAY Sports

Forte was a dual-threat running back for the Bears in the 2010s. He was the centerpiece of a great offense that also featured Jay Cutler, Brandon Marshall, Martellus Bennett and Alshon Jeffrey. The Bears didn't win a lot when he was there, but he gave Bears fans a lot to cheer for every season. He accumulated five 1,000 yard seasons and made just one playoff trip with the Bears in 2010.

 
12 of 25

12. Olin Kreutz

Olin Kreutz
Jonathan Daniel-Staff-Getty Images

Kreutz shined as a football player at his high school in Hawaii and at the University of Washington. He started 183 games for the Bears and was the Iron Man of the offensive line during four playoff trips. He was the starting enter for the 2006 NFC champion Bears that lost the Super Bowl to Peyton Manning's Colts. As a center, one of the most grueling positions in football, he managed to play 13 seasons and was one of the best centers of his era. He also rocked the half-cage facemask, so you have to like him.

 
13 of 25

13. Doug Buffone

Doug Buffone
Manny Rubio-USA TODAY Sports

The kid from rural Pennsylvania was a great outside linebacker for the Bears. A maestro at tackling, he led the Bears to two playoff trips. The longtime Bear played a whopping 186 games for the Windy City. When he hung up his cleats in 1979, he was the last Bear to play for legendary Bears head coach George Halas. 

 
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14. Jim Osborne

Jim Osborne
Darryl Norenberg-USA TODAY Sports

After a standout career at Southern University, an HBCU in Louisiana, Osborne balled for the Bears. Born in Sylvania, Georgia, he was country strong. The do-it-all defensive lineman retired in 1984. If he had only stayed on the team for one more season, he could've been a Super Bowl champion.

 
15 of 25

15. Mike Hartenstine

Mike Hartenstine
Manny Rubio-USA TODAY Sports

A Penn State alum, Hartenstine made the Pro Football Writers Association All-Rookie Team in 1975. At 32 years old, he won the Super Bowl with the 1985 Bears. He made the 4-6 Defense work like so many other great defensive lineman on the team.

 
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16. Richie Petitbon

Richie Petitbon
Green Bay Press-Gazette-USA TODAY NETWORK

Petitbon was a winner. He won the 1963 NFL Championship with the Bears; it was George Halas' last ring. The hard-hitting safety had 48 interceptions and three pick-sixes, including a 101-yarder in 1962. The four-time Pro Bowler retired in 1972. He won three Super Bowls as the Washington's defensive coordinator in the 1980s and 1990s and was head coach Joe Gibbs' right-hand man.

 
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17. Keith Van Horne

Keith Van Horne
Manny Rubio-USA TODAY Sports

Van Horne was the 1985 Bears' starting right tackle, and he helped paved the way for the Bears' victory in Super Bowl XX. His contributions to the run game were indispensable as he blocked for Payton during some of his best seasons.

 
18 of 25

18. Joe Fortunato

Joe Fortunato
Robert Riger-Contributor-Getty Images

An All-American fullback at Mississippi State University, Fortunato was a great linebacker from the 1950s and 1960s. He won the 1963 NFL Championship with the Bears, Halas' last ring. He's a member of the 1950s All-Decade Team. Fortunato played next to Dıck Butkus toward the end of his career and showed the all-time great how it's done.

 
19 of 25

19. Mark Bortz

Mark Bortz
Manny Rubio-USA TODAY Sports

Bortz was a good luck charm for the Bears. The left guard was part of eight playoff trips, earning them all. The two-time Pro Bowler was a great run blocker for the Bears' smashmouth offense. A stalwart on the offensive line, he rarely missed a game and was a starter on the 1985 Bears. 

 
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20. Charles Tillman

Charles Tillman
Brad Mills-USA TODAY Sports

Tillman was the shutdown cornerback of the great Bears defenses of the 2000s. He covered the opposing team's best players as the Bears clawed their way to a Super Bowl appearance in 2006 and a trip to the NFC Championship Game in 2010. His battles with Detroit Lions wide receiver Calvin Johnson were legendary. His best ability was his knack for causing forced fumbles. The Peanut Punch, as it came to be known, was his signature move. In 2012, he led the league in forced fumbles with 10.

He won the Walter Payton NFL Man of the Year award in 2013, one of the only Bears to win this award. In 2015, he signed with the Carolina Panthers, who went 15-1 and lost to Peyton Manning in Super Bowl 50. Both of Tillman's Super Bowl losses were to Peyton Manning.

 
21 of 25

21. Doug Atkins

Doug Atkins
Malcolm Emmons-USA TODAY Sports

The Hall of Fame defensive end won two NFL Championships. He won it all with the Cleveland Browns in 1954 and again with the Bears in 1963. At 6-foot-8, he was a giant — one of the biggest players from his era. He was the best end of his time and helped defined the modern defensive end along with fellow Hall of Famer Gino Marchetti, who played for the Baltimore Colts.

 
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22. Jay Cutler

Jay Cutler
Kim Klement-USA TODAY Sports

When the Bears traded for Cutler in 2009, he was hailed as the savior of their long-standing quarterback problem. The Bears were armed with one of the best defenses in football, and Cutler felt like the missing piece to a Super Bowl squad. The Bears were contenders in the early going with Cutler. 

A knee injury kept him out of the second half of the 2010 NFC Championship Game against the Green Bay Packers. With Cutler sidelined due to injury, the Packers won the game and then the Super Bowl that year. Chicago never forgave Cutler for declining to play the conference championship game and questioned his toughness. While he's the best quarterback in franchise history, he never won the Big Game and the team regressed every season he was there. 

After football, he became a reality TV show star. He has the distinction of sharing the same name as four-time Mr. Olympia-winning bodybuilder Jay Cutler. It's hilarious they share the same name because they couldn't be any different.

 
23 of 25

23. Rosey Taylor

Rosey Taylor
Herb Weitman-USA TODAY Sports

Taylor racked up many standout seasons over his pro career. None were better than 1963, when he led the league in interceptions with nine and helped the Bears win the NFL Championship. The two-time pro Bowler was a ballhawk for the Bears. He also played for the 49ers and Commanders.

 
24 of 25

24. Neal Anderson

Neal Anderson
RVR Photos-USA TODAY Sports

After an exceptional college career with the Florida Gators, Anderson was drafted to be Payton's backup. He played this role for two seasons. When Payton retired, Anderson was thrown into the starting lineup and given the impossible task of succeeding Sweetness. Anderson did a great job as his replacement. He rushed for three 1,000-yard seasons and carried the offense to many playoff trips — just like Payton before him. The four-time Pro Bowler made the Windy City proud.

 
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25. James Williams

James Williams
Peter Brouillet-USA TODAY Sports

Williams played college ball at Cheyney University, a small HBCU in Pennsylvania. He's the best player their football program ever produced. He joined the team as a defensive lineman and switched to right tackle, where he shined. He made the Pro Bowl in 2001 and was a mainstay on the line, starting in 143 games and not missing a single game from 1995-2002. He was also skilled at blocking field goals on special teams. 

David J. Hunt is a freelance writer based out of Philadelphia. He ran cross country at Penn State, became a volunteer firefighter during COVID-19, and is a self taught journalist. He's a diehard Philly sports fan. When he isn't watching sports, he enjoys working out, fishing, and traveling. You can find more of his writing at The Chestnut Hill Local and The Temple News. You can follow him on Twitter at @dave_hunt44.

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