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Last Updated: February 15, 2021

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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

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