Ranking the Top 25 Chicago Cubs Players of All-Time: Numbers 25-21

Chicago Cubs

Ranking the top 25 Chicago Cubs players of all-time is a tall task, considering the franchise dates back more than 140 years. The Cubs have not been one of the most successful franchises in baseball history, but there have been some great players that have worn the Cubbie blue.

Some of these Cubs legends played well before television was invented, but the numbers still speak for themselves. Others helped the Cubs break the longest curse in professional sports history, earning them a permanent space in Cubs lore.

Each day I will break down five of the best to ever put on the Cubs uniform, and give my biased opinion on why they are ranked in that spot. This wasn’t easy, and leaving off some of my favorite current players was not an easy decision to make, but it simply had to be done.

And without further ado, here are the greatest players in Chicago Cubs history (Numbers 25-21):

25: Mark Grace

First baseman Mark Grace played for the Cubs from 1988-2000 and was, unfortunately, a part of some bad teams. Grace was arguably the best player on a number of those Cubs teams but was overshadowed by another star when the team started to improve.

Grace was known for his slick-fielding, and for his ability to spray the ball all over the field. Grace batted in the middle of the lineup for the Cubs and was a huge part of the Cubs Wild Card winning team in 1998.

Mark Grace is in the top-10 for a number of statistical categories including on-base percentage, doubles, walks, and runs batted in. If you were a Cubs fan in the 1990s, there is a good chance that Grace was your favorite player.

The big first baseman would go on to win a World Series with the Arizona Diamondbacks in 2001.

24: Kyle Hendricks

“The Professor” is the nickname given to Kyle Hendricks for his ability to carve up opposing offenses. The current starting pitcher for the Chicago Cubs has already become a legend, and there is still time for him to climb up the rankings.

Hendricks has been a member of the Cubs since 2014 and has already pitched in some of the biggest games in franchise history. The Professor was the winning pitcher in Game 7 of the NLCS in 2016, and also started Game 7 of the World Series that season.

In 2016, Hendricks led the National League with a 2.13 earned run average, and was third in the Cy Young voting that season. Hendricks is still outside of the top-10 in most categories in Cubs history, but there is no doubt that he is one of the best pitchers the team has ever had.

23: Andre Dawson

Andrew Dawson, “The Hawk,” is one of the best players to ever put on a Cubs uniform, but unfortunately spent just six years in Chicago. Dawson is famous for giving the Cubs a blank check and letting them pay him whatever the team wanted.

In 1987, “The Hawk,” won the MVP Award of the National League, despite playing for the last-place Chicago Cubs. Dawson was named to five straight All-Star teams as a member of the Cubs and was eventually enshrined in Cooperstown.

Dawson was a powerful hitter at the plate but was most known for his defense and exceptional throwing arm. Right field bleacher bums adored Dawson, and he is still a huge fan favorite.

22: Lee Smith

Hall of Famer Lee Smith spent the first eight years of his 18-year career with the Chicago Cubs, and is the best closer in franchise history. Smith recorded 180 saves during his career with the Cubs and averaged more than 8.5 strikeouts per nine innings.

Smith made just one postseason appearance with the Cubs in 1984, and unfortunately, things did not go well for the closer. That small blemish does not take away from the great career Smith had that started on the North Side.

The hard-throwing right-hander finished his career with a 3.03 earned run average to go along with 478 career saves.

21: Rick Sutcliffe

Sutcliffe cemented his place in Cubs lore in 1984 when he promptly when 16-1 after being traded from the Cleveland Indians. Sutcliffe would go on to win the National League Cy Young Award that season after helping to lead the Cubs to a division title.

The current ESPN broadcaster went 82-65 over eight seasons with the Cubs, and went 1-1 with a 3.72 ERA in the postseason. Sutcliffe continues to work with the team in Spring Training, and the older generation of Cubs fans will tell you about how dominant he was during that magical run in 1984.

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About Ryan Burks 110 Articles
Ryan has been writing sports betting content and industry news pieces for more than 3 years. He stays on top of all of the latest industry news as well as providing sports betting strategy articles and opinion pieces. Ryan is a former college basketball player and someone that continues to participate in sports to this day. He is a die-hard fan of the Chicago Cubs and Chicago Blackhawks and also roots for the Fighting Illini. Ryan currently resides in Illinois