By Ty Bronicel 
Introduction
In the world of sports, few accolades carry the weight and significance of having your jersey number retired by a team. This gesture honors the remarkable achievements and lasting legacy of athletes who have left an indelible mark on their sport. This article explores the legacies of iconic players from Chicago teams whose numbers have been retired, celebrating their extraordinary contributions to basketball, baseball, and football. The Chicago Bulls will retire former NBA MVP Derrick Rose’s No. 1 jersey during the 2025–26 NBA season.
1. Michael Jordan – Chicago Bulls, No. 23
Michael Jordan, widely regarded as the greatest basketball player of all time, led the Chicago Bulls to six NBA championships (1991–93, 1996–98). He was a five-time NBA MVP and six-time NBA Finals MVP. Jordan’s iconic No. 23 jersey was retired by the Bulls in 1998, honoring his unparalleled legacy.
2. Greg Maddux – Chicago Cubs, No. 31
Greg Maddux, a legendary pitcher, spent 10 seasons with the Chicago Cubs, earning a 186-104 record with a 3.12 ERA. Maddux won four Cy Young Awards and was an eight-time All-Star. His jersey number 31 was retired by the Cubs in 2009, honoring his remarkable career achievements.
3. Walter Payton – Chicago Bears, No. 34
Walter Payton, nicknamed “Sweetness,” is widely regarded as one of the greatest football players of all time. A nine-time Pro Bowl selection, Payton is the second-leading rusher in NFL history (16,726) and fifth all-time in rushing touchdowns (110). He led the Chicago Bears to a Super Bowl XX victory in 1985 and was inducted into the Pro Football Hall of Fame in 1993. His jersey number, 34, was retired by the Bears in honor of his incredible contributions to the team.
4. Ernie Banks – Chicago Cubs, No. 14
Ernie Banks, known as “Mr. Cub,” played 19 seasons with the Chicago Cubs from 1953 to 1971. A two-time NL MVP and 11-time All-Star, Banks hit 512 home runs and had 1,636 RBIs. His jersey number 14 was retired by the Cubs in 1982. Banks was inducted into the Baseball Hall of Fame in 1977.
5. Gale Sayers – Chicago Bears, No. 40
Gale Sayers, known as “The Kansas Comet,” was a legendary running back for the Chicago Bears. He played from 1965 to 1971, earning four Pro Bowl appearances and five first-team All-Pro selections. Sayers set numerous records, including scoring 22 touchdowns in his rookie season and tying the record for six touchdowns in a single game. His jersey number 40 was retired by the Bears in recognition of his outstanding contributions to the team.
6. Ryne Sandberg – Chicago Cubs, No. 23
Ryne Sandberg, a Hall of Fame second baseman, played 16 seasons with the Chicago Cubs. He won nine Gold Glove Awards and was named the 1984 NL MVP. Sandberg led the Cubs to their first postseason appearance since 1945 and holds multiple records for second basemen, including most Gold Glove Awards and consecutive errorless games. His jersey number 23 was retired by the Cubs in 2005, the same year he was inducted into the Baseball Hall of Fame.
7. Dick Butkus – Chicago Bears, No. 51
Dick Butkus, a legendary linebacker, played for the Chicago Bears from 1965 to 1973. Renowned for his fierce tackling and relentless effort, he was a five-time first-team All-Pro and eight-time Pro Bowl selection. Butkus recovered 27 fumbles and intercepted 22 passes, earning him the title of the NFL’s most feared tackler. His jersey number 51 was retired by the Chicago Bears in recognition of his outstanding contributions to the team.
8. Fergie Jenkins – Chicago Cubs, No. 31
Fergie Jenkins, a Hall of Fame pitcher, played for the Chicago Cubs from 1966 to 1973 and again in 1982-1983. He won 167 games with the Cubs, including six consecutive 20-win seasons from 1967 to 1972. Jenkins was the first Canadian to win the Cy Young Award in 1971.
9. Billy Williams – Chicago Cubs, No. 26
Billy Williams, a six-time All-Star, played for the Chicago Cubs from 1959 to 1974. He holds numerous team records for left-handed hitters, including 392 home runs and 2,510 hits. Williams’ career statistics include a .290 batting average, 2,711 hits, 426 home runs, and 1,475 RBIs. His number 26 was retired by the Cubs in 1987, following his induction into the National Baseball Hall of Fame.
10. Brian Piccolo – Chicago Bears, No. 41
Brian Piccolo, a running back for the Chicago Bears, had his jersey number 41 retired in his honor. Despite his short career, Piccolo made a lasting impact, rushing for 927 yards and scoring 5 touchdowns from 1966-1969. His courageous battle with cancer at age 26 cemented his legacy as a symbol of courage and friendship.
Conclusion
Reflecting on the careers of these legendary athletes, it’s clear that their impact extends far beyond the sports they played. Their retired numbers symbolize not only personal accomplishments but also the lasting inspiration they provide to fans and future generations. These icons have not only defined the standards of greatness in their respective sports but have also solidified their places in sports history.