Cubs players who have appeared in the most World Series

What Cubs have played in the most World Series?

When talking about the Cubs and the World Series, what comes to mind the most is the 1908 Cubs and the 2016 Cubs. The Cubs players from the 1930s get ignored a lot. The Cubs were in three World Series that decade. Guys like Stan Hack and Gabby Hartnett.

First, the Cubs from the 1908 series. Then we’ll list all the 1930s Cubs players with the most World Series appearances.

That crew from 1908 played in four World Series (1906, 1907, 1908, 1910). There are a ton of players from that span.

  • Johnny Kling (1906, 1907, 1908, 1910)
  • Frank Schulte
  • Jimmy Sheckard
  • Harry Steinfeldt
  • Joe Tinker
  • Frank Chance
  • Mordecai Brown
  • Orval Overall
  • Ed Reulbach
  • Jack Pfiester
  • Ed Reulbach
  • Orval Overall
  • Mordecai Brown

Missing from this list is Johnny Evers of the famous “Tinkers to Evers to Chance” combination. Of the 13 players from this time to appear in all four World Series, you’d think Tinkers, Evers, and Chance would appear in the list. Johnny Evers didn’t play in the 1910 World Series.

On October 21, 1910, just as the season was ending, the Cubs were gearing up to face the Athletics in the World Series when disaster struck during a series with the Cardinals: Johnny Evers fractured his ankle.

The Tribune wrote:

These are the saddest of possible words
“Evers is out of the game.”
Though the Cubs have subs to throw at the birds,
Evers is out of the game.
Deep in the hearts of Cub fans woe doth rankle;
Bender and Coombs have both won, and now Plank’ll
Turn the same trick—why did John break his ankle!—
“Evers is out of the game!”

The Cubs appeared in five World Series from 1929 to 1945.

Three players have appeared in four World Series.

  • Gabby Hartnett (1929, 1932, 1935, 1938)
  • Charlie Root (1929, 1932, 1935, 1938)
  • Stan Hack (1932, 1935, 1938, 1945)

2016 Cubs

Looking at World Series appearances isn’t quite fair to today’s players. In 1945, there were only 16 teams total in both leagues. Today each LEAGUE has 15 teams (for 30 total). Maybe we should count appearances in the National League Championship Series?

No Cub has appeared in four NLCS. The most appearances a Cub has made in the NLCS is three. They are all from 2015, 2016, and 2017.

  • Anthony Rizzo (2015, 2016, 2017)
  • Kris Bryant
  • Javier Baez
  • Pedro Strop
  • Kyle Schwarber
  • Héctor Rondón
  • Tommy La Stella
  • Jon Lester
  • Kyle Hendricks
  • Jake Arrieta

If the Cubs make the NLCS again, Kyle Hendricks has a chance at making Cub history.

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