Top 50 Chicago Cubs

When it comes to iconic sports teams in North America, few can come close to the Chicago Cubs.

The Cubs first came into existence in 1870 as the Chicago White Stockings would join the National League in 1876.  Before 1900, Chicago was one of the most successful teams.  Led by Cap Anson, Chicago would win the National League Pennant in 1876, 1880, 1881, 1882, 1885 & 1886.  They would go through a couple of name changes to the Colts, Orphans and would officially adopt the name of the Cubs in 1903.

The Cubs did well in the first decade of the 1900s where with stars like Joe Tinker, Johnny Evers, Frank Chance, and Three Finger Brown and would win the World Series in 1907 and 1908.  That would begin the longest championship drought in sports.

You know the story.  The alleged curse of the goat.  Steve Bartman. 

It would take until 2016 when they would win the World Series again, although they did win the National League Pennant multiple times between them (1910, 1918, 1929, 1932, 1935, 1938 & 1945).  They also had Hall of Famers at that time, like Ernie Banks and Ryne Sandberg.

As of this writing, three World Series Championships is not very many for a team that has been around since the beginning, but again, how many organizations are as well known as the Cubbies!


Not too many!

This list is up to the end of the 2019 season.

Note: Baseball lists are based on an amalgamation of tenure, traditional statistics, advanced statistics, playoff statistics, and post-season accolades.

1. Cap Anson

1. Cap Anson
Top 50 Chicago Cubs
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Arguably the first superstar in baseball history, Cap Anson joined the then named Chicago White Stockings in 1876 and would become one of the greatest hitters of the game for years.  In the 22 years he played in Chicago, Anson batted over .300 in 19 of them including a 15-year streak (1876 to 1890), and he would win three Batting Titles and four second place finishes in that stretch.  Anson would find other ways to get on base as the superstar was also a three-time leader in On Base Percentage and finished second in that statistic four times.  His hits…
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2. Ernie Banks

2. Ernie Banks
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In terms of overall iconic status at Wrigley Field, Ernie Banks would be number 1.  Of course, he would!  He is "Mister Cub" after all!
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3. Ryne Sandberg

3. Ryne Sandberg
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Ryne Sandberg arrived in Chicago via one of the most lopsided trades in baseball history as the future Hall of Fame arrived with Larry Bowa for Ivan DeJesus.  Sandberg was converted to an infielder, and after playing only six games in the Majors with Philadelphia, he would be converted from Outfield to Third Base (he would then move to Second a year after)
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4. Ron Santo

4. Ron Santo
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Ron Santo would crack the Majors with the Cubs in 1960, and the Third Baseman would quickly establish himself as one of the premier men at the hot corner, both with his bat and glove over the next decade-plus.  Santo would tabulate an impressive 2,171 Hits as a Cub and even more impressively knew the art of getting on base.  Santo led the NL in Walks four times and was a two-time leader in On Base Percentage.
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5. Billy Williams

5. Billy Williams
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Billy Williams played the first 14 of his 16 seasons with the Chicago Cubs, where he quickly established himself as one of the best hitting Leftfielders in the game.  Williams would win the Rookie of the Year Award in 1961 with a 25 Home Run season.  Power would be a big part of his game, as he blasted 20 or more taters the next 12 seasons and a career-high of 42 in 1970.  That year, the six-time All-Star would lead the NL with 205 Hits, and 137 Runs Scored, and Willians would have a .322 Batting Average, and he was…
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6. Sammy Sosa

6. Sammy Sosa
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The Cubs fleeced their cross-town rival White Sox when they acquired Sammy Sosa for George Bell as Sosa would become one of the best offensive players of his day while Bell was on his way out of the game.
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7. Ferguson Jenkins

7. Ferguson Jenkins
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The greatest Pitcher in Chicago Cubs history, Ferguson Jenkins arrived in what turned out to be a lopsided trade from the Philadelphia Phillies.  The Canadian born Jenkins would break out in his first full season (1967) with the Cubs where he would be named an All-Star, win 20 Games, and was the runner-up for the Cy Young.
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8. Mordecai Brown

8. Mordecai Brown
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If you didn't agree that Fergie Jenkins was the best Pitching Chicago Cub, then we guess that it was Mordecai "Three Finger" Brown that you would give that title too.
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9. Gabby Hartnett

9. Gabby Hartnett
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Gabby Hartnett was considered the best Catcher in the National League (maybe all of baseball) for a decade, and why wouldn't he be?
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10. Stan Hack

10. Stan Hack
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An upper-tier Third Baseman and longtime leadoff man, “Smilin" Stan Hack would play all 1,938 of his Major League games with the Chicago Cubs.  Hack cracked the Cubs roster in 1932, and in 1934 he was affixed as the permanent player at the hot corner.  As the team's leadoff man, he would display consistent hitting with a lifetime Batting Average of .301 and five top ten finishes in that metric.  He did not just hit is way on base as he was a patient batter who knew how to work the count.  He had an excellent On-Base Percentage of .394,…
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11. Hippo Vaughn

11. Hippo Vaughn
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James “Hippo” Vaughn was a journeyman who bounced around from the minors to the majors from team to team for a few years before he found a home in Chicago in 1913.  He broke out with a 21 Win season in 1914 and had 20 Wins in 1915, and in 1917 he would have a career-high 23 Wins and an ERA of 2.01.  In '16 and '17, he was third among Pitchers in bWAR, but in 1918 he would have one of the best years that a hurler ever had as a Cub.  Vaughn would lead the National League in…
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12. Pete Alexander

12. Pete Alexander
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Grover Cleveland "Old Pete" Alexander far and away had a much better career earlier when he was with the Philadelphia Phillies, where he had won the Pitcher's Triple Crown twice. Still, the Phillies needed the money and sold his contract to the Chicago Cubs.
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13. Charlie Root

13. Charlie Root
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Many great Pitchers have toiled on the mound for the Chicago Cubs, but none of them have recorded more Wins than Charlie Root, who brought the “W” 201 times.
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14. Frank Chance

14. Frank Chance
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One third of the famed Cubs infield of Tinker to Evers to Chance, Frank Chance was the final cog of that triumvirate playing at First Base. 
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15. Rick Reuschel

15. Rick Reuschel
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Nicknamed “Big Daddy” for his portly physique, Rick Reuschel is now viewed as a sabermetric star, and most of those accomplishments took place as a Chicago Cub.
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16. Billy Herman

16. Billy Herman
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A multi-time All-Star, Billy Herman helped the Chicago Cubs reach the World Series three times.  Chicago may not have won any of the Fall Classics, but he was a vital cog in the machine that brought excitement to Wrigley Field for a decade.
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17. Joe Tinker

17. Joe Tinker
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It began with Joe Tinker, at least that is how the poem goes of Tinker to Evers to Chance in regards to turning double plays for the Chicago Cubs in the 1900s.
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18. Bill Nicholson

18. Bill Nicholson
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This is as good a time as any to remind everyone that we don't put substantial penalties those who put up their best statistics during World War II when many of the game's greats were serving in the military.  It does play a bit when we focus on intangibles, but it is about what they do on the diamond and not what is going on around them, which is paramount in our eyes.
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19. John Clarkson

19. John Clarkson
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Cap Anson was the player/manager for the Chicago White Stockings, and he saw future greatness in John Clarkson, who was playing for Saginaw in the Northwest League, and he would urge Chicago ownership to purchase his contract.  Clarkson won 10 games for the team in what was left of the season, and he would become the elite Pitcher of the National League in 1885 leading the league in Wins (53), Innings Pitched (623.0), bWAR (12.9) and posting an ERA of 1.85.  He would go 36 and 17 in 1886, and in 1887 his 38 Wins would again lead the NL…
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