George Halas was one of the most polarizing figures of the early NFL. He was a player, coach, general manager and owner of the Chicago Bears, and he was the only person involved with each of the league’s first 60 seasons. Halas was good at wearing down other owners and players to accept deals and contracts, although he was not shy about spending money in the right places. Since he was the owner until his death in 1983, he was responsible for the first seven trades on this list, which brought the Bears six Hall of Fame players and four titles (a fifth would come a little more than two years after Halas died). 

One trade that did not make the cut was the Draft-day deal three years ago, in which Chicago sent first-, third- and fourth-round picks in 2017 and a third-rounder in 2018 to San Francisco in order to move up one spot and draft North Carolina quarterback Mitchell Trubisky second overall in 2017. The 49ers followed by drafting defensive tackle Solomon Thomas and also took linebacker Fred Warner the following year. San Francisco traded the 2017 third-round pick to New Orleans (running back Alvin Kamara) and the fourth-rounder to Seattle (safety Tedric Thompson). 

1. August 16, 1938:

Bears acquired: A first-round pick in the 1939 NFL Draft

Pittsburgh Pirates acquired: WR/End Edgar “Eggs” Manske

The pick the Bears acquired in the trade, Columbia quarterback Sid Luckman, paid immediate dividends, leading Chicago to four championships overall and three in his first four years in the Windy City. In his 12 NFL seasons, Luckman led the league in passing yards and touchdowns three times each, including 1943, when he won the Joe F. Carr Trophy as MVP after totaling 2,194 yards and a career-high 28 scores. The 1965 Hall of Famer was also a five-time All-Pro and a three-time Pro Bowler. Luckman ranks second in team history with 14,686 yards and 137 touchdowns. 

The Pittsburgh Pirates began play in 1933 and were awful for their first seven seasons before changing their name to the Steelers in 1940. Typical of those early Pittsburgh teams, the Pirates had the second pick in the 1939 draft, which they traded to the Bears to acquire Manske in an attempt to bolster their receiving corps. After two solid seasons with the Eagles, Manske had two more decent years with the Bears, but he lasted just six games in Pittsburgh. He was released after the 1938 season and returned to Chicago for two more seasons, retiring after making his lone Pro Bowl in 1940. Manske totaled 70 receptions, 1,467 yards, and 11 touchdowns in six years. 

Assessment: This deal is one of the most lopsided in NFL history. Luckman was one of the league’s stars throughout the 1940s, while Manske played just six games in Pittsburgh before returning to Chicago. The entire trade was indicative of the early days of the Steelers franchise. Trading away a top pick for no long-term help is certainly one of the reasons why Pittsburgh made the playoffs just once in its first 37 seasons of existence. BEARS

2. December 11, 1939:

Bears acquired: RB George McAfee

Eagles acquired: T Russ Thompson and T Milt Trost

Luckman was the main reason the Bears became the class of the NFL in the 1940s, but he certainly was not the team’s only star. McAfee was selected by the Eagles with the second overall pick in the 1940 Draft. The speedy Duke graduate was given the nickname “One-Play” by fans and reporters because he was capable of scoring every time he had the ball in his hands. The 1966 Pro Football Hall of Famer was a Pro Bowler and an All-Pro in 1941, when he scored five touchdowns. McAfee was a member of three championship teams and totaled 1,685 yards and 21 scores in eight seasons. He would have had more if he hadn’t missed three years while serving in the Navy during World War II.

Chicago had a knack for finding stellar offensive linemen in its early years, with Joe Stydahar and George Connor manning the left tackle position in the 1940s, making Thompson and Trost expendable. Both retired after playing just one season in Philadelphia, with Thompson starting five games and Trost two in 1940.

Assessment: Here is an example of a team trading from a position of strength to improve a weaker part of its roster. McAfee teamed with Luckman and star receiver Ken Kavanaugh to create a formidable offense that won three championships (both McAfee and Kavanaugh missed the fourth title Chicago won during World War II). BEARS

3. July 11, 1955:

Bears acquired: DE Doug Atkins and S Ken Gorgal

Browns acquired: Third- and sixth-round picks in the 1956 NFL Draft

Atkins was another in the long-line of Hall of Famers to don the blue and orange Bears uniform. A first-round pick in the 1953 NFL Draft, Atkins played just 20 games in two seasons with the Browns before the trade. In Chicago, he made eight Pro Bowls in 12 years and was an All-Pro in 1963. Atkins played in two NFL Championship Games with the Bears. He was a reserve in a 47-7 loss to the Giants in 1956 and a starter in a 14-10 win against New York in 1963 that was the team’s last title until Super Bowl XX in 1985. Gorgal had six interceptions in 1955, but feuded with Bears owner George Halas and was released midway through the following season. He signed with the Packers and had two picks before retiring in 1957. 

The third-round pick was University of Denver’s end/receiver Larry Ross, who never played in the NFL. Ross was one of the last stars from Denver to be drafted, since the university ended its football program in 1960. The sixth-round pick was Sherman Plunkett, an offensive tackle from Maryland State (now called Maryland-Eastern Shore). He never played for the Browns, instead, he spent two years in the U. S. Army after being drafted in 1956. Following his military service, Plunkett signed with the Colts and won two titles in his first three seasons, including the 1958 title game against the Giants, known as the “Greatest Game Ever Played.” He spent the rest of his career in the AFL, playing two seasons with the Chargers and earning two Pro Bowl selections in five years with the Jets before retiring in 1967. 

Assessment: Although Plunkett had a solid professional career, he did not play with the Browns. Atkins was a Hall of Famer who gave Chicago more than a decade of stellar play and appeared in two NFL Championship Games. BEARS

4. December 2, 1963:

Bears acquired: A first-round pick in the 1965 NFL Draft

Steelers acquired: Second- and fourth-rounders in 1964

The Bears certainly seem to get the better of all of these trades, especially the ones with the Pittsburgh franchise. This was just supposed to be a simple deal that gave the Steelers more picks now for a big one later. However, that early draft pick ended up REALLY big. Dick Butkus was a two-time All-American at Illinois, earned Pro Bowl honors in his first eight NFL seasons, and was also a five-time All-Pro. Known for his fierceness and intimidation, Butkus is also Chicago’s all-time leader with 27 fumble recoveries and amassed 22 career interceptions. The 1979 Pro Football Hall of Famer also has his name on the award that has been given to the best linebacker in high school, college and the NFL since 1985. 

Pittsburgh’s first pick from this deal was Jim Kelly (no relation to the Bills’ Hall of Fame quarterback), a Notre Dame graduate who converted from wide receiver to tight end in the NFL. He spurned the AFL’s Patriots, who drafted him early in the second round in 1964, but played just one season with the Steelers. Kelly signed with the Eagles, totaling 345 yards and four touchdowns in 1967 before retiring. This fourth-round pick was Jackson State defensive end, Ben McGee. He chose to play with the Steelers instead of the Jets, who drafted him in the fifth round of the AFL Draft. McGee played nine seasons with the Steelers, earning Pro Bowl selections in 1966 and ’68, but retired before Pittsburgh unveiled its “Steel Curtain” defense. His final game was the Steelers’ loss to the perfect Dolphins in the 1972 AFC Championship Game. Once his playing career ended, McGee turned to coaching, and he spent four years leading Arkansas-Pine Bluff in the early 1980s. 

Assessment: McGee was a solid player, but Butkus’ hard-nosed style of play made him one of the NFL’s stars during the early Super Bowl era. BEARS

5. May 3, 1977:

Bears acquired: QB Mike Phipps

Browns acquired: A fourth-round pick in the 1977 NFL Draft and a first-round selection in 1978

Phipps was a major piece in another memorable trade, when he went from Miami to Cleveland for Hall of Fame wide receiver Paul Warfield. Phipps was inconsistent with the Browns, leading them to a 10-3 record in 1972, but managing just a 24-25-2 mark overall in seven seasons with Cleveland. After the trade to Chicago, he was a reserve for the first two years. Phipps led the Bears to a 9-1 record in 10 starts in 1979, but Chicago lost to Philadelphia in the Division Round. He retired in 1981 after coming off the bench for two more seasons. 

The 1977 fourth-round pick was Robert “Mickey” Sims, a defensive tackle from South Carolina State. He played 43 games with the Browns in three seasons before retiring in 1979 to become a park ranger and police officer. Sims died of a heart attack in 2006. His son, Rob Jr., played nine seasons in the NFL with the Seahawks and Lions. Cleveland traded the 1978 first-rounder, enabling the Los Angeles Rams to move up three spots and draft Oklahoma running back Elvis Peacock. In exchange, the Browns received two picks, including fourth-rounder Pete Pullara, a guard from Tennessee-Chattanooga who never played in the NFL. The first-round pick in the deal turned into Alabama tight end Ozzie Newsome, who became a Browns icon. The 1999 Hall of Famer was a three-time Pro Bowler and an All-Pro in 1984. 

Assessment: Chicago finally ends up on the wrong end of one of these deals, thanks to Cleveland’s shrewd Draft-day trade. BROWNS

6. April 12, 1978:

Bears acquired: A first-round pick in the 1979 NFL Draft and a player to be named later

Buccaneers acquired: DT Wally Chambers

In the same draft that the Bills acquired the first overall pick from the 49ers for O. J. Simpson, the Bears moved up and took Arkansas defensive lineman Dan Hampton at the fourth spot. Hampton spent 12 seasons in Chicago, starting at both end and tackle on a Bears defense that was one of the best in NFL history. “Danimal” was a four-time Pro Bowler and an All-Pro in 1984 when he had a career-high 11½ sacks. Hampton posted a sack and a fumble recovery in the Bears’ 46-10 blowout win over the Patriots in Super Bowl XX, and his 57 sacks rank third in team history. He retired in 1990 after having undergone ten knee surgeries in his career. Hampton was inducted into the Pro Football Hall of Fame in 2002. The player to be named was tight end Bob Moore, who totaled 114 catches, 1,262 yards and seven touchdowns in eight seasons with the Raiders, Buccaneers, and Broncos. He was cut by Chicago during training came in 1978 and did not have a catch in eight games that year with Denver before retiring. 

Chambers was the 1973 Defensive Rookie of the Year, made three Pro Bowls and earned All-Pro honors in 1976. After the trade, he started 18 of 28 games with the Buccaneers before he retired in 1979. 

Assessment: Chicago got the best years out of Chambers, then traded him and drafted Hampton, who was one of the stars of a Super Bowl-winning defense. BEARS

7. April 28, 1981:

Bears acquired: A second-round pick in the 1981 NFL Draft

49ers acquired: Second- and fifth-round picks in 1981

Speaking of defensive stars in the 1980s, the second-round pick the Bears acquired in this deal became their Super Bowl centerpiece. Linebacker Mike Singletary was a two-time All-American and a two-time Southwest Conference Player of the Year with Baylor. In Chicago, he was a two-time Defensive Player of the Year while joining Bill George and Dick Butkus as legendary Bears middle linebackers. “Samurai” went to 10 straight Pro Bowls, earned seven All-Pro selections and was named the NFL’s Man of the Year in 1990. Singletary recovered two fumbles in Super Bowl XX and was inducted into the Pro Football Hall of Fame in 1998. 

San Francisco used the second-round pick on Missouri cornerback Eric Wright, who played on four Super Bowl winners, starting in two of those victories. He picked off a career-high seven passes in 1983 and earned Pro Bowl selections the following two years. Wright was an All-Pro in 1985, but missed most of the next two seasons with a pulled groin and chipped bone. He returned in a reserve role as San Francisco won two straight titles in Super Bowls XXIII and XXIV. The fifth-rounder was Arrington Jones, a running back from Winston-Salem State. Jones had 43 yards on three kickoff returns in his only game with the 49ers in 1981. He signed with the Washington Federals of the United States Football League in 1983, but was cut before the team’s first game. Jones became a college coach in 1986 and most recently served as offensive coordinator at Delaware State. 

Assessment: Wright was on his way to becoming a star in San Francisco before his injuries, but Singletary’s presence and production gave Chicago a title and the edge in this trade. BEARS

8. February 18, 1997:

Bears acquired: QB Rick Mirer and a fourth-round pick in the 1997 NFL Draft

Seahawks acquired: A first-round pick in 1997

Mirer was a high school All-American and a talented player at Notre Dame who was billed as the “next Joe Montana.” So what did Seattle get out of the second overall pick in 1993? In four seasons, Mirer amassed 9,094 yards, 41 touchdowns, 56 interceptions, and posted a paltry 20-31 record. He lasted just one year in Chicago after the trade, with an 0-3 record and six picks and no touchdowns. Mirer lost his starting job to Erik Kramer and was released after the 1997 season. He played one year with the Jets and two each with the 49ers and Raiders before he retired in 2004. The fourth-round pick was Northwestern running back Darnell Autry, who finished fourth in the 1995 Heisman Trophy voting (won by Ohio State running back and future Tennessee Titans star Eddie George). Autry had 319 yards and one touchdown in 1997 with the Bears, but he did not play again until 2000, when he signed with the Eagles and totaled 609 yards and four scores in his final season. 

The Seahawks sent the acquired pick (which became Nebraska cornerback Michael Booker) along with three others to the Falcons for the two draft choices. Shawn Springs was an All-American cornerback with Ohio State in 1996. The third overall pick in 1997, Springs had 20 interceptions in seven years with Seattle, including seven in 1998, when he made his only Pro Bowl. Springs signed with the Redskins in 2004 and had 12 picks in five years with Washington. He spent one final year with New England before retiring in 2009. The second pick acquired from Atlanta was sent to Tampa Bay in a deal that included the pick that became Warrick Dunn in exchange for the sixth overall selection in 1997. With that pick, Seattle took Florida State tackle Walter Jones, who was a nine-time Pro Bowler and a four-time All-Pro. He started 10 playoff games, including a loss to the Steelers in Super Bowl XL. Jones was selected to the Pro Football Hall of Fame in 2004. 

Assessment: No matter what player Seattle got, they would have won this trade. Selecting a solid starting cornerback AND a Hall of Fame lineman that helped the team reach a Super Bowl turned out to be a wise use of resources. SEAHAWKS

9. April 17, 1999:

Bears acquired: First-, third-, fourth- and fifth-round picks in the 1999 NFL Draft and a third-rounder in 2000

Redskins acquired: A first-round pick in 1999

You would think that at least one of the five players Chicago acquired in this deal would have been a solid NFL performer, but that wasn’t the case. The Bears’ first pick was Cade McNown, a 1998 All-American and Heisman Trophy finalist in 1998. However, he never was able to get on track in the NFL, posting a 3-12 record in two seasons. His poor play and attitude caused him to be traded to the Dolphins in 2001 and then to the 49ers the following year, but he did not appear in a game for either team and retired in 2003. The 12th spot where McCown was selected originally belonged to the Saints, but was one of eight picks New Orleans sent to Washington in order to move up and draft Texas running back (and ’98 Heisman winner), Ricky Williams. The third-rounder also came from the Saints deal and was used on D’Wayne Bates, a star wide receiver at Northwestern. Bates is still the Wildcats’ all-time leader in receptions, yards, and touchdowns, but he started just two games in three seasons with the Bears. He had one good season with the Vikings in 2002, but was out of the NFL two years later. 

Chicago selected Texas A&M linebacker Warrick Holdman in the fourth round. Holdman had 3½ sacks and 351 tackles in five seasons with the Bears, then spent one year with the Browns and two with the Redskins. He signed with the Broncos in 2008, but did not appear in a game with Denver and retired the following year. The fifth-round selection was Jerry Wisne, a high school All-American at offensive tackle who played in college at Notre Dame. Wisne appeared in seven games with the Bears as a rookie, but was relegated to the team’s practice squad the following season. After a year on Minnesota’s practice squad, he signed with Green Bay and played two games in 2002. He retired after failing to appear in a game with the Packers the next season. The third-rounder in 2000 was Dustin Lyman, a linebacker at Wake Forest who converted to tight in the NFL. Lyman had just 37 catches and three touchdowns in five seasons with the Bears before retiring in 2004. He became a business executive after his playing career, eventually rising to CEO of the Famous Brands International food company in 2016. 

The Redskins used the seventh overall pick to select Roland “Champ” Bailey, who was a 1998 All-American at cornerback with Georgia. He spent his first five seasons in Washington, amassing 18 interceptions while earning All-Rookie Team honors and four Pro Bowl selections. In 2004, Bailey was traded to Denver along with a draft pick for another star in running back Clinton Portis. 

Assessment: As stated at the beginning of this breakdown, none of the five Bears acquisitions amounted to much in the NFL, while Bailey earned four Pro Bowl nods and was on his way to a Hall of Fame career. REDSKINS

10. September 1, 2018:

Bears acquired: LB Khalil Mack along with second- and seventh-round picks in the 2020 NFL Draft

Raiders acquired: First- and sixth-round picks in 2019 and first- and third-round picks in 2020

Although several of the players in this trade have not played a game yet in the NFL, Mack has been a star in two seasons with the Bears. Oakland traded him to cut salary, and Mack has been to a pair of Pro Bowls with Chicago and was named an All-Pro in 2019 after posting 12½ sacks. He also has made 94 tackles and forced 11 fumbles the past two years. The Bears may have found another gem in former Notre Dame tight end Cole Kmet, who was taken in the second round in this year’s draft. The only issue with Kmet is a broken collarbone that caused him to miss three games as a junior in 2019. The seventh-round pick was Arlington Hambright, an offensive tackle from Colorado. 

Mack is a fantastic player, but he Raiders by no means got fleeced by this deal. The 2019 first-rounder was running back Josh Jacobs, who was part of Alabama’s National Championship team in 2017. Jacobs made the Pro Football Writers of America All-Rookie Team last season after leading all first-year players with 1,150 yards and seven rushing touchdowns. The sixth-round pick was part of a complicated web of trades in the 2019 Draft that included separate deals with six other teams. In the end, Oakland ended up with the following players: Second-rounder Trayvon Mullen, a two-time National Champion with Clemson who started 10 games for the Raiders at cornerback in 2019; fourth-round pick Isaiah Johnson, a University of Houston product who played five games as a reserve safety; another fourth-rounder, former LSU tight end Foster Moreau, who had 21 catches and five touchdowns as a rookie; fifth-round pick Hunter Renfrow was a teammate of Mullen’s with Clemson and ranked third in the Raiders with 605 yards and four scores in 2019; finally, seventh-rounder Quinton Bell was a defensive end from Prairie View A&M who was cut in training camp and spent the season on Tampa Bay’s practice squad. The 2020 picks were Ohio State cornerback Damon Arnette, who was taken in the first round and third-rounder Bryan Edwards, a wideout who holds South Carolina records for catches and receiving yards.

Assessment: Five years from now, this trade assessment could look quite a bit different, since most of these players are still being evaluated based on potential, rather than production. Jacobs and Renfrow could be stars in the making and will definitely lead the youth movement in Las Vegas, but Mack is the only fully proven commodity so far in this trade, giving Chicago the edge. BEARS

All NFL statistics and awards courtesy of https://www.pro-football-reference.com/

Next: Cincinnati Bengals

Writer

-By: Kevin Rakas

Thanks to the coaching of George Halas and one of the most balanced teams in NFL history, the Chicago Bears won seven titles in 10 NFL Championship Game appearances over their first 27 years of existence. The franchise has played in just four title games since 1947, winning twice, including a dominating performance against the Patriots in Super Bowl XX. Many of Chicago’s best draft picks have come from one of those two eras, although some of the best players graced Soldier Field during the lean years in the 1960s and ’70s. 

BEST

10. (tie) Dan Hampton, DE (Round 1, Pick 4 in 1979) and Jim Covert, T (Round 1, Pick 6 in 1983) - These two were stars on their respective lines during the 1980s. Hampton was an All-American and the Southwest Conference Defensive Player of the Year at Arkansas in 1978. He was scouted by future Bears head coach Mike Ditka, who was an assistant coach with the Cowboys at the time, but Chicago grabbed him early and he was a member of the All-Rookie Team. The following year, he unofficially recorded 11½ sacks and made his first Pro Bowl. Hampton went to four Pro Bowls overall, and tied his career-high with 11½ sacks in 1984, when he also earned his only All-Pro selection. Known for his fierce play, “Danimal” ranks third in Bears history with 57 sacks, and he added eight more in the postseason, including one in Super Bowl XX. The 2002 Pro Football Hall of Famer currently hosts a show for Pro Football Weekly. 

A 1982 All-American at Pittsburgh, Covert started immediately at left tackle with the Bears. He was both a Pro Bowler and an All-Pro in 1985 and ’86, and he was part of Chicago’s Super Bowl XX-winning squad. Covert started 15 games in 1990, but retired after missing all of the 1991 seasons due to back surgery. He was selected to the Pro Football Hall of Fame as part of the NFL100 Centennial Class this year. Covert has worked in healthcare sales and marketing since leaving the NFL. 

9. (tie) Joe Stydahar, T (Round 1, Pick 6 in 1936), Danny Fortmann, G (Round 9, Pick 78 in 1936), Clyde Turner, C (Round 1, Pick 7 in 1940) and Stan Jones, G (Round 5, Pick 55 in 1953) - Like many youths who grew up in West Virginia during the early part of the 20th century, Stydahar joined his father working in coal mines. He was known for being one of the best tacklers in college football while at West Virginia, and he soon brought his vicious style of play to Chicago. Stydahar was the Bears’ first-ever draft pick, and he earned four Pro Bowl and four All-Pro selections during a nine-year career that included a two-year hiatus in which he served as a lieutenant in the U. S. Navy during World War II. Chicago went to six NFL Championship Games during Stydahar’s tenure and won four, including 1946, which was his final game. After his playing career, the 1967 Hall of Famer was a head coach with the Cardinals and Rams. He passed away in 1977. 

Selected eight rounds after Stydahar, Fortmann stayed with the Bears after coach and owner George Halas gave him money so he could attend medical school during his playing career. Fortmann was selected to six All-Pro teams and three Pro Bowls in eight NFL seasons. He played in five championship games with the Bears, and retired after winning his third title in 1943. Fortmann later earned his medical degree, became a lieutenant with the Navy Medical Corps during World War II and worked as a surgeon in Los Angeles for nearly 40 years. The 1965 Pro Football Hall of Famer was later diagnosed with Alzheimer’s disease and died in 1995 at age 79. 

Turner went from weighing 175 pounds as a freshman at Hardin-Simmons University in Texas to a 235-pound star who was given the nickname “Bulldog” by his teammates. After the Lions were fined for trying to persuade Turner to play for them as a pro by paying for his dental work in college, the Bears drafted him and signed him to a three-year contract. In 13 NFL seasons, Turner, who played at both center and linebacker, was selected to seven All-Pro teams and four Pro Bowls. Chicago won four titles in five attempts during his career, and he had 17 interceptions, including a league-leading eight in 1942. Turner coached the New York Titans in 1962, the final season before they became the Jets, and he was inducted into the Pro Football Hall of Fame in 1966. He died from lung cancer in 1998.

The fourth of Chicago’s unsung offensive linemen at this spot is Jones, an All-American during Maryland’s National Championship season in 1953. He started his pro career at the tackle spot, but split time at guard as well. During his 12-year tenure in Chicago, Jones was selected to seven Pro Bowls, three All-Pro teams and appeared in two championship games, winning a title with the Bears in 1963. He signed with the Redskins, where he spent his final season before retiring. Jones was an avid weightlifter, and was one of the first players to use that as part of football conditioning. Another Pro Football Hall of Fame inductee, Jones served as a defensive line and strength and conditioning coach in the NFL for nearly 25 years. He passed away in 2010. 

8. Bill George, LB (Round 2, Pick 23 in 1951) - Through the years, the Bears have been blessed with four of the greatest middle linebackers in NFL history, and all of them are on this list. George, a Wake Forest product, started his pro career in the middle guard spot, which was part of the five-man defensive front that was common in the NFL during the early 1950s. After being moved to linebacker, George became a star. He was selected to eight straight Pro Bowls (1954-61) and was an eight-time All-Pro in 14 years with Chicago. George posted 18 interceptions, 17 fumble recoveries and was one of the team’s leaders during the 1963 championship season. The man some call the “meanest Bear ever” retired after spending the 1966 season with the Rams. He died in an automobile accident in 1982.

7. Sid Luckman, QB (Round 1, Pick 2 in 1939) - The Bears have been unlucky at the quarterback position, but Luckman is the exception. A Brooklyn native, Luckman attended nearby Columbia University, where he finished third in the 1938 Heisman Trophy voting. Halas used Luckman in the T-formation, in which the quarterback is under center with three running backs behind. The system worked, with Luckman leading the Bears to five NFL Championship Games and four titles in 12 seasons. He was a five-time All-Pro, a three-time Pro Bowler and he won the Joe F. Carr MVP Award after leading the NFL with 2,194 yards and 28 touchdowns in 1943. He ranks second in Bears history with 14,686 yards and 137 scoring passes, and he led the league in each category three times. After retiring as a player in 1950, Luckman was vice president and quarterbacks coach with Chicago, and he was also the president of a cellophane products company. He died in 1998. 

6. (tie) Olin Kreutz, C (Round 3, Pick 64 in 1998), Brian Urlacher, LB (Round 1, Pick 9 in 2000) and Lance Briggs, LB (Round 3, Pick 68 in 2003) - Three players who appeared in Super Bowl XLI are at this spot. Kreutz was an All-American and Morris Trophy recipient (one of two awards given to the best on both the offensive and defensive lines in the Pac-10) at Washington in 1997. Throughout his 13 years in Chicago, Kreutz went to six straight Pro Bowls (2001-06) and was an All-Pro in 2006. The season ended with the Bears appearing in the first Super Bowl in 21 years. He signed with the Saints for one season and retired in 2011. Kreutz currently works with Bears local radio and television coverage.

Urlacher is another of the wildly successful middle linebackers to have donned a Bears jersey. He was an All-American with New Mexico in 1999, and went on to play 13 seasons in Chicago. Urlacher earned eight Pro Bowl and four All-Pro selections, including both honors during the 2006 Super Bowl XLI season. He also was the NFL Defensive Rookie of the Year in 2000 and Defensive Player of the Year in 2005. Urlacher is the team’s all-time leader with 1,361 tackles, ranks seventh with 41½ sacks and is tied for sixth with 11 forced fumbles. He retired after the 2012 season and was inducted into the Pro Football Hall of Fame in 2018. 

Briggs joined Urlacher in making life miserable for opposing offenses throughout the early 2000s. The Arizona product ranks second in Bears history with 1,181 tackles, tied for third with 16 forced fumbles and also returned five of his 16 interceptions for scores. The seven-time Pro Bowler and 2005 All-Pro made 13 tackles in a loss to the Colts in Super Bowl XLI. He currently works as a Bears analyst on NBC Sports Chicago, along with former teammates Kreutz, Matt Forte, and Alex Brown. 

5. Richard Dent, DE (Round 8, Pick 203 in 1983) - Dent might not have had the personality of fellow “Super Bowl Shuffle” video stars William “The Refrigerator” Perry or Jim McMahon, but he was the most productive player on the defense that dominated the NFL in 1985 and routed the Patriots in Super Bowl XX. Dent is the franchise’s all-time leader with 124½ sacks, and he had 10 or more in eight of his 12 seasons with Chicago. The Tennessee State product was selected to four Pro Bowls and was an All-Pro in 1985, when he led the NFL with 17 sacks. Dent also ranks second in Bears history with 34 forced fumbles, including leading the league twice. He also spent one season each with the 49ers, Colts and Eagles, winning a title with San Francisco in 1994. Dent had a falling out with the team after his playing career ended, and he took any mention of former Bears coach Mike Ditka out of his 2011 Hall of Fame induction speech. 

4. Mike Singletary, LB (Round 2, Pick 38 in 1981) - One of the most intimidating players in the history of the NFL was drafted by the Bears after earning All-American and Southwest Conference Player of the Year honors in 1979 and ’80. From 1983-92, Singletary was selected to 10 straight Pro Bowls, seven All-Pro teams and won Defensive Player of the Year honors in 1985 and ’88. “Samurai Mike” finished his 12-year NFL career with 19 sacks, 12 fumble recoveries and seven interceptions. Although tackles were not an official statistic during his playing career, Singletary is unofficially credited with 1,488 stops. He retired in 1992, and began coaching in 2003. He had an 18-22 record in parts of three seasons as head coach with the 49ers before he was fired in 2010. The 1998 Pro Football Hall of Famer is now a motivational speaker and has co-authored four books. 

3. Gale Sayers, RB (Round 1, Pick 4 in 1965) - Sayers was a track star in high school who became a two-time All-American rusher at Kansas. He chose Chicago over Kansas City, who selected him fifth overall in the AFL Draft. As a rookie, Sayers scored a league-record 22 touchdowns (an NFL-high 14 rushing, six receiving, one kick return and one punt return). He was an All-Pro his first five seasons, and was selected to four Pro Bowls. The “Kansas Comet” led the league in rushing yards twice (1966 and ’69) and he still holds 20 Bears records. Sayers also ranks fifth in club history with 4,956 rushing yards, 39 touchdowns on the ground and 2,781 kickoff return yards, and he holds the team’s all-time record with six kick return scores. Unfortunately, knee injuries hampered Sayers late in his career: He tore several ligaments in his right knee in 1968, and a 1970 injury resulted in two surgeries on his left knee and ultimately led to his retirement before the 1972 season. Sayers is also known for his friendship with fellow running back Brian Piccolo, which was the inspiration for the movie Brian’s Song. The two were the first interracial roommates in the NFL, and Sayers was present during Piccolo’s battle with a rare form of cancer that claimed his life in 1970. After his career, Sayers was an athletic director at Southern Illinois and ran a computer supply company. Like many players in his era, Sayers has dealt with issues from previous concussions, and he was diagnosed with dementia in 2013. 

2. Dick Butkus, LB (Round 1, Pick 3 in 1965) - There are some names that, when you hear them, you know they belong to a hard-nosed football player. Eagles great Chuck Bednarik is one, and Butkus is certainly another. The two-time All-American at Illinois chose the Bears over the Broncos, who selected him in the AFL Draft. In his nine-year career, Butkus was selected to eight Pro Bowls and five All-Pro teams. He is the Bears all-time leader with 27 fumble recoveries, and also had 22 interceptions. “The Animal” earned his nickname in a 1969 game against the Steelers, when he recorded a safety and made a ridiculous 25 tackles. A lingering right knee injury forced him to retire after the 1973 season. The Bears tried to cut him out of his contract, which included paying for needed medical expenses and care, so Butkus sued the team and the sides settled out of court.  Butkus became a broadcaster and actor after his playing career, and he also runs a charitable foundation. The Hall of Famer and NFL100 member also has an award named after him, given to the best linebacker in high school, college and the NFL. 

1. Walter Payton, RB (Round 1, Pick 4 in 1975) - A Jackson State graduate, Payton was seen as the next coming of Sayers, who had retired four years earlier, and he certainly met those expectations. . Payton retired 13 years later as the NFL’s all-time leading rusher after passing Jim Brown for the top spot in 1984. “Sweetness” was a nine-time Pro Bowler and a five-time All-Pro, who also earned MVP and Offensive Player of the Year honors after leading the league with 1,852 yards and 14 touchdowns in 1977. Payton had 10 seasons with at least 1,200 yards, and reached double-digit touchdowns five times. Despite being on the downside of his career, he totaled 1,551 yards and nine scores in the Super Bowl XX season in 1985. After splitting carries with Neal Anderson in 1987, Payton retired after the season with Bears records of 16,726 yards and 110 touchdowns, with his rushing mark standing until Emmitt Smith topped it in 2002. After his playing career, Payton owned an IndyCar racing team and an Illinois restaurant chain. He was diagnosed with primary sclerosing cholangitis, a rare liver disease that led to bile duct cancer and claimed his life in 1999. One of the most beloved figures in Chicago sports history, Payton has had several tributes throughout the city, including his name on a high school and on the hill where he used to train. Also, the city created a special sticker and license plate in his honor. Payton’s name is now on Jackson State’s training center, and he even has an asteroid named after him. The NFL also renamed their honor for playing excellence, volunteer and charity work the Walter Payton NFL Man of the Year Award. 

WORST

10. Rex Grossman, QB (Round 1, Pick 22 in 2003) - Grossman had a distinguished career, both in high school and college, but could not match that production in the NFL. USA Today named him Indiana Player of the Year in 1998 as a high school senior, and Grossman then redshirted in his first year at Florida in 1999. He was an All-American and the SEC Player of the Year in 2001, and he also finished second behind Eric Crouch in the Heisman Trophy voting. But Grossman spent most of his first three professional seasons on the bench thanks to knee and ankle injuries, as well as erratic play. Despite another inconsistent season in 2006, he started every game as the Bears rode their defense to Super Bowl XLI, where Grossman threw for 165 yards, one touchdown and two interceptions in a loss to the Colts. After two more seasons in Chicago, he signed with the Texans. He totaled 10,232 yards and 56 touchdowns in 10 seasons with Chicago, Houston, and Washington before retiring in 2012. 

9. Marc Colombo, T (Round 1, Pick 29 in 2002) - Colombo earned All-Big East honors with Boston College in 2001. His 6-foot-8, 320-pound frame would have been a big help to Chicago’s offense, but he could not stay healthy. Colombo suffered a dislocated patella and femoral nerve damage in November of his rookie year, and he also missed the entire 2003 season and half of 2004. The Bears released him after one game in 2005, and he latched on with the Cowboys, where he started 72 games over the next six years. After one season in Miami, Colombo retired in 2011, and was recently hired as the Giants’ offensive line coach. 

8. (tie) Alonzo Spellman, DE (Round 1, Pick 22 in 1992), John Thierry, DE (Round 1, Pick 11 in 1994) and Michael Haynes, DE (Round 1, Pick 14 in 2003) - Spellman was a USA Today All-American and the New Jersey Player of the Year as a high school senior in 1988. He then moved from linebacker to defensive end at Ohio State, and earned All-Big Ten honors in 1991. Once drafted, Spellman took over for Richard Dent in Chicago and performed fairly well, amassing 32 sacks in six years. However, his time with the Bears was marked by erratic behavior that led to a diagnosis of bipolar disorder. He refused to take his medication, instead relying on alcohol and illicit drugs, which led to Chicago releasing him in 1997. The Cowboys signed him two years later and got him to take his medication, but he retired in 2001. After his career, Spellman got involved with mixed martial arts.

Thierry was a linebacker at Alcorn State before being converted to a defensive end in Chicago. He started just 28 games in five seasons with the Bears, registering 12½ sacks and 88 tackles. Thierry played for the Browns, Packers and Falcons over his final four years, totaling 21 sacks in that time. He died of a heart attack in 2017. 

While at Penn State, Haynes was named Big Ten co-Defensive Player of the Year in 2002 (along with Ohio State safety Mike Doss). Selected eight picks before Grossman, Haynes lasted just three seasons with Chicago, starting four of 43 games and posting only 5½ sacks. After the Bears traded for star defensive end Adewale Ogunleye from the Dolphins, Haynes bulked up and tried to make an impact as a defensive tackle, to no avail. The Bears released him before the 2006 season, and he did not sign with another team despite tryouts with the Saints and Jets. After his playing career ended, Haynes has been a high school coach, a manager with USA Football and an owner of his own consulting company. 

7. Rashaan Salaam, RB (Round 1, Pick 21 in 1995) - Salaam’s 1994 season at Colorado was one of the most productive campaigns in recent memory. He ran for 2,055 yards and 24 touchdowns (both school records), while also winning the Heisman Trophy and earning All-American honors. While he ran for 1,074 yards and 10 scores as a rookie with Chicago, his NFL career did not have the same success thanks to concussion issues and marijuana use. He finished with 1,682 yards in three seasons with the Bears, missed the 1998 season after failing his physical and played just two games with the Browns the following year. Salaam played with the XFL’s Memphis Maniax in 2001, but his tryout with the 49ers the next season was unsuccessful. Salaam was found dead in a Colorado park in 2016, which was ruled a suicide. Although he had alcohol and THC in his system, he had also struggled with depression stemming from head trauma sustained during his football career, though his family refused tests to determine if he had a CTE-related injury.

6. Stan Thomas T (Round 1, Pick 22 in 1991) - With several players from the Super Bowl XX era starting to retire, the Bears needed to revamp their offensive line. However, the 1991 Draft proved to be a poor year for linemen. Only one offensive lineman drafted that year made the Pro Bowl (tackle Erik Williams, who the Cowboys drafted in the third round). Thomas lasted just two years in Chicago, where he clashed with head coach Mike Ditka, got arrested for a DUI and refused to enter rehab, which resulted in a trade to the Falcons. He was then shipped to the Oilers, where he played two more years before he was out of the NFL after the 1994 season. Thomas was arrested after sexually assaulting a woman in 2004. 

5. David Terrell, WR (Round 1, Pick 8 in 2001) - Terrell was an All-American in high school in Virginia (1997) and college (2000 at Michigan). His NFL career lasted just four seasons, and his totals of 128 catches, 1,602 yards and nine touchdowns did not match his potential coming out of college. Terrell signed with Denver and lasted just one game in 2005. He was acquitted of drug charges in 2013, but was arrested the following year after assaulting his ex-girlfriend. 

4. Kevin White, WR (Round 1, Pick 7 in 2015) - White earned All-Big 12 honors after a 1,447-yard, 10-touchdown season at West Virginia in 2014. However, he missed his rookie season after suffering a shin injury that required the insertion of a steel rod into his left leg. He then suffered a fractured tibia after playing four games in 2016, and appeared in just one game the following season due to a fractured left shoulder blade. White played nine games in 2018, but finished his Bears career with just 25 receptions for 285 yards. He signed with Arizona in 2019, but was cut in training camp due to a hamstring injury. 

3. Cedric Benson, RB (Round 1, Pick 4 in 2005) - Benson was a two-time All-Big 12 recipient and an All-American in 2004. He ran for 5,540 yards and 64 touchdowns in four years at Texas. Benson began his Bears career backing up Thomas Jones before ascending to the starting role in 2007. But head coach Lovie Smith again turned to Jones during the playoffs, although Benson did have 60 yards and a touchdown in Super Bowl XLI before leaving the game with a knee injury. He also had problems with alcohol, and the Bears released him in 2008 after he was arrested twice in a little more than a month. Benson signed with the Bengals, where he ran for at least 1,000 yards in three of his four seasons. He was arrested twice while he was with Cincinnati, and was released again in 2011. He retired after spending one season with the Packers. Benson was arrested for DWI in 2017. He and a female passenger died in August 2019 when his motorcycle struck a minivan on a Texas roadway. 

2. Cade McNown, QB (Round 1, Pick 12 in 1999) - McNown was a 1998 All-American and Heisman Trophy finalist (won by Texas running back Ricky Williams), and he still holds quite a few UCLA passing records. But he was inconsistent throughout his two seasons with Chicago, compiling a 3-12 record and posting a 16-19 touchdown-to-interception ratio. McNown was traded to Miami in 2001, and he spent the season as the third-string quarterback. The Dolphins sent him to the 49ers, but he had shoulder surgery and never played in the NFL again. Since his retirement in 2002, McNown has held positions at banks and investment firms.  

1. Curtis Enis, RB (Round 1, Pick 5 in 1998) - While at Penn State, Enis was a Big Ten co-Freshman of the Year in 1995 (with Michigan defensive back Charles Woodson) and both an All-American and Big Ten co-Offensive Player of the Year in 1997 (with Iowa running back Tavian Banks). He held out after the Bears drafted him, but he had a decent rookie season (497 yards) before tearing his ACL. Enis posted a career-high 916 yards and three touchdowns in 1999, but a degenerative knee injury caused him to retire two years later. Even worse, the Bears could have had Fred Taylor or Randy Moss at this spot. 

All NFL statistics and awards courtesy of https://www.pro-football-reference.com/ and college football statistics and awards courtesy of https://www.sports-reference.com/cfb/

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-By: Kevin Rakas

Writer