Ranking the Top 25 Chicago Cubs Players of All-Time: Numbers 20-16


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.

All-Time Cubs Numbers 25-21

And without further ado, here are the greatest players in Chicago Cubs history (Numbers 20-16):

20: Derrek Lee

After helping to rip the hearts out of Cubs fans in 2003, first baseman Derrek Lee came over to Chicago from the Florida Marlins. Lee would go on to deliver plenty of big moments for the Cubs and turn the heartbreak into happiness.

In seven seasons with the Cubs, Lee hit 179 home runs, drove in 574 runs, and had a batting average of .298. Lee also saved plenty of bad throws from his infielders, winning the Gold Glove three times during his Cubs tenure.

In 2005, Lee led the National League with 199 hits, 50 doubles, and a .335 batting average. The Cubs won two division titles with Lee in the middle of the lineup.

19: Kerry Wood

May 6, 1998 is a date that every Cubs fan older than 25 will remember. On this date, Kerry Wood announced his presence with a 20-strikeout performance in what is arguably the greatest game ever pitched.

“Kid K” would go on to the win Rookie of the Year Award that season, and helped push the Cubs to a playoff berth. Despite some arm injuries throughout his career, Wood was one of the best pitchers in Cubs history.

In 2003, Wood went 2-0 in the NLDS against the Atlanta Braves, including winning Game 5 of that series. He would later transition to the bullpen and helped lead the team to back-to-back NL Central titles in 2007 and 2008.

Kerry Wood is a legend in Chicago and remains one of the most beloved players of all-time.

18: Bruce Sutter

Hall of Fame closer Bruce Sutter is next on the list, even though he is wearing a St. Louis Cardinals cap in Cooperstown. Sutter picked up 133 saves as a member of the Chicago Cubs, and many of them were multi-inning appearances.

Sutter spent just five seasons with the Cubs, but was an All-Star four straight seasons. In 1979, Sutter was named Cy Young in the National League after posting 37 saves and a 2.22 earned run average.

His career with the Cubs was not long enough for Cubs fans, but he is without a doubt one of the best to ever wear that uniform.

17: Aramis Ramirez

The Cubs were looking for an offensive spark in 2003, and they found it in a trade with the Pittsburgh Pirates. Landing third baseman Aramis Ramirez not only delivered a NL Central title that season, A-Ram became one of the best to ever wear the uniform.

Ramirez played just nine seasons with the Cubs, but put up some monster offensive numbers during that time. Ramirez blasted 232 home runs in Chicago, which is sixth best in franchise history.

Ramirez was also a huge part of two other division titles with the Cubs in 2007 and 2008. Cubs fans will remember Ramirez as a clutch performer that always seemed to deliver a big hit.

16: Jon Lester

Current Cubs fans know that the path to the 2016 World Series began when Jon Lester signed on as a free agent. Since that time, all Lester has done has delivered in big games when it has mattered most.

In six seasons with the Cubs, Lester has gone 77-44 with a 3.64 earned run average. Lester is a two-time All Star with the Cubs and finished in second place in the Cy Young race in 2016.

Numbers don’t tell the whole story with Lester, and he will be most remembered for what he brought to this organization. The Lovable Losers became a force to be reckoned with when Jon Lester put on that Cubs uniform for the first time.

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About Ryan Burks 112 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