Top 10 List: The Greatest Chicago Cubs of All Time

The Top Ten Greatest Chicago Cubs of All Time Introduction 10.) Mark Grace Mark Grace played for the Chicago Cubs and the Arizona Diamondbacks. 3 Time MLB All – Star (1993, 1995, 1997) World Series Champion (2001) 4 Time Gold Glove Award (1992, 1993, 1995, 1996) 9.) Andre Dawson Andre...

April 16, 2026 • 7:14 AM

The Top Ten Greatest Chicago Cubs of All Time

Introduction

10.) Mark Grace

Mark Grace played for the Chicago Cubs and the Arizona Diamondbacks.

3 Time MLB All – Star (1993, 1995, 1997)

World Series Champion (2001)

4 Time Gold Glove Award (1992, 1993, 1995, 1996)

9.) Andre Dawson

Andre Dawson played for the Montreal Expos, the Chicago Cubs, the Boston Red Sox, and the Florida Marlins.

8 Time MLB All – Star (1981, 1982, 1983, 1987, 1988, 1989, 1990, 1991)

National League MVP (1987)

National League Rookie of the Year (1977)

8 Time Gold Glove Award (1980, 1981, 1982, 1983, 1984, 1985, 1987, 1988)

4 Time Silver Slugger Award (1980, 1981, 1983, 1987)

National League Home Run Leader (1987)

National League RBI Leader (1987)

Montreal Expos Number 10 Retired

8.) Fergie Jenkins

Fergie Jenkins played for the Philadelphia Phillies, the Chicago Cubs, the Texas Rangers, and the Boston Red Sox.

3 Time MLB All – Star (1967, 1971, 1972)

National League Cy Young Award (1971)

2 Time Wins Leader (1971, 1974)

National League Strikeout Leader (1969)

Chicago Cubs Number 31 Retired

Texas Rangers Hall of Fame

7.) Sammy Sosa

Sammy Sosa played for the Texas Rangers, the Chicago White Sox, the Chicago Cubs, and the Baltimore Orioles.

7 Time MLB All – Star (1995, 1998, 1999, 2000, 2001, 2002, 2004)

National League MVP (1998)

6 Time Silver Slugger Award (1995, 1998, 1999, 2000, 2001, 2002)

National League Hank Aaron Award (1999)

Roberto Clemente Award (1998)

2 Time National League Home Run Leader (2000, 2002)

2 Time National League RBI Leader (1998, 2001)

6.) Greg Maddux

Greg Maddux played for the Chicago Cubs, the Atlanta Braves, the Los Angeles Dodgers, and the San Diego Padres.

8 Time MLB All – Star (1988, 1992, 1994, 1995, 1996, 1997, 1998, 2000)

World Series Champion (1995)

4 Time National League Cy Young Award (1992, 1993, 1994, 1995)

18 Time Gold Glove Award (1990, 1991, 1992, 1993, 1994, 1995, 1996, 1997, 1998, 1999, 2000, 2001, 2002, 2004, 2005, 2006, 2007, 2008)

3 Time MLB Wins Leader (1992, 1994, 1995)

4 Time MLB ERA Leader (1993, 1994, 1995, 1998)

Chicago Cubs Number 31 Retired

Atlanta Braves Number 31 Retired

Braves Hall of Fame

5.) Cap Anson

Cap Anson played for the Rockford Forest Citys, the Philadelphia Athletics, and the Chicago White Stockings / Colts.

2 Time National League Batting Champion (1881, 1888)

8 Time National League RBI Leader (1880, 1881, 1882, 1884, 1885, 1886, 1888, 1891)

6 Time National League Pennant (1876, 1880, 1881, 1882, 1885, 1886)

4.) Billy Williams

Billy Williams played for the Chicago Cubs and the Oakland Athletics.

6 Time MLB All – Star (1962, 1964, 1965, 1968, 1972, 1973)

National League Rookie of the Year (1961)

National League Batting Champion (1972)

Chicago Cubs Number 26 Retired

3.) Ron Santo

Ron Santo played for the Chicago Cubs and the Chicago White Sox.

9 Time MLB All – Star (1963, 1964, 1965, 1966, 1968, 1969, 1971, 1972, 1973)

5 Time Gold Glove Award (1964, 1965, 1966, 1967, 1968)

Chicago Cubs Number 10 Retired

2.) Ryne Sandberg

Ryne Sandberg played for the Philadelphia Phillies and the Chicago Cubs.

10 Time MLB All – Star (1984, 1985, 1986, 1987, 1988, 1989, 1990, 1991, 1992, 1993)

National League MVP (1984)

9 Time Gold Glove Award (1983, 1984, 1985, 1986, 1987, 1988, 1989, 1990, 1991)

7 Time Silver Slugger Award (1984, 1985, 1988, 1989, 1990, 1991, 1992)

National League Home Run Leader (1990)

Chicago Cubs Number 23 Retired

1.) Ernie Banks

Ernie Banks played for the Kansas City Monarchs and the Chicago Cubs.

14 Time MLB All – Star (1955, 1956, 1957, 1958, 1959, 1960², 1961², 1962², 1965, 1967, 1969)

2 Time National League MVP (1958, 1959)

Gold Glove Award (1960)

2 Time National League Home Run Leader (1958, 1960)

2 Time National League RBI Leader (1958, 1959)

Chicago Cubs Number 14 Retired

Major League Baseball All – Century Team