Ranking the Top 25 Chicago Cubs Players of All-Time

Baseball, MLB article at Knup Sports

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.

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 25-1):

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.

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.


15 Anthony Rizzo

Anthony Rizzo is the unofficial “Captain” of the current Chicago Cubs, and he played a key role in getting this franchise turned around. Rizzo is one of the best defensive players in the league and has been a consistent slugger in the middle of the Cubs lineup.

Kris Bryant might have won an MVP Award, and Javy Baez is extremely popular, but Rizzo is clearly the heart and soul of the current Cubs team. Rizzo has blasted 228 home runs and driven in 744 runs during his nine seasons in Chicago.

Rizzo was also the player that caught the final out that shattered a 108-year championship drought. There have been other players post better numbers, but Rizzo is a Chicago Cubs legend.

14 Phil Cavarretta

Phil Cavarretta made his debut with the Cubs at just 17 years of age, and went on to star with the team for two decades. Cavarretta won MVP of the National League in 1945, the last time the Cubs had won the pennant since 2016.

Cavarretta was an All Star four different times during his 20 year Cubs career, and was known for his speed and his terrific defense. His 1,927 hits ranks 10th all-time in Cubs history, but he played during an era when offenses were not putting up a ton of runs.

His 1,953 games played with the Cubs is the sixth-most in team history. Cavarretta is another player that emerged before most our of time, but he is one of the best in franchise history.

13 Stan Hack

Hack was a teammate of Cavarretta’s during the 30’s and 40’s, but he was a much better offensive performer. Hack never won an MVP Award during his career, but he is one of the best Cubs’ hitters of all-time.

During his 16-year Cubs career, Hack posted a batting average of .301 and collected 2,193 hits. He is sixth all-time for number of hits, and also ranks in the top ten in runs, doubles, triples, total bases, and at-bats.

Another player that would have looked great at the top of the Cubs order in 2020, Hack made the most of his career, which was entirely spent with the Cubs.

12 Mordecai Brown

Mordecai “Three Finger Brown” began his Cubs career in 1904 and spent 10 season on the North Side during his illustrious career. Some of the numbers are eye-popping when looking at Brown’s career stats, but there is no video evidence to show his dominance.

Brown posted a 188-86 record as a member of the Cubs, and sported a 1.80 earned run average. The game was played a lot differently during his time, but ole “Three Finger” was one of the earliest legends in the game.

The Cubs won a pair of World Series titles in 1907 and 1908 with Brown leading the way. More than 100 years later, he is still regarded as one of the best to ever wear a Cubs uniform.

11 Hack Wilson

Hall of Fame outfielder, Hack Wilson spent just six years with the Chicago Cubs, but put up some monster numbers during that time. Wilson finished in the top-12 in MVP voting four straight seasons from 1926-1929.

Most baseball fans have heard all about the 1927 New York Yankees, but Wilson was doing his own slugging in the Windy City. In 1930, Wilson led the league with 56 homes runs and 191 runs batted in.

During his first give seasons with the Cubs, Wilson averaged 35 home runs and 141 runs batted in. He was one of the most feared hitters of his time, and is often overlooked by baseball historians.

Hack Wilson had ridiculous power, and it’s too bad that those numbers were largely wasted on bad teams. The slugger sits just outside of the top-10 on this list, but he is one of the best to ever play for the Cubs.

10. Frank Chance

Most Cubs fans can recite the famous double-play combination in the early 1900s of Tinkers to Evers to Chance. First baseman Frank Chance was the best of that group and begins the top-10 of this countdown.

Chance is the Cubs’ all-time leader stolen bases with 402, and he is in the top-10 in several other statistical categories. It’s almost impossible for Cubs fans to believe this, but Chance made four World Series appearances with the Cubs, including winning the title in 1907 and 1908.

In 15 seasons with the Cubs, Chance posted an on-base percentage of .394. Chance was inducted into the Baseball Hall of Fame in 1946 by the Old Timers Committee.

9. Gabby Hartnett

Catcher Gabby Hartnett played 19 seasons with the Chicago Cubs and was a perennial All-Star during that time. Hartnett made six consecutive All-Star appearances from 1933-1938 and was named MVP of the National League in 1935.

Hartnett sits inside the top-10 in a number of Cubs offensive and defensive categories and was one of the stars of baseball during the 1930s. Hartnett has seemed to be overlooked by a large majority of Cubs fans, but he lands at number nine on this list.

In 1955, Hartnett was elected to the Hall of Fame, capping off an illustrious career. There have been some solid catchers in the history of the Cubs, but Hartnett was by far the best to ever play that position.

8. Cap Anson

Cap Anson is the only player on this list to have played his entire career in the 1800s, making it hard to compare him to more recent greats. His career numbers are simply too hard to ignore, as is the fact that he spent 22 seasons with the Cubs.

Anson is the Cubs all-time leader in hits (3,012), runs (1,722), runs batted in (1,880), doubles (529) and WAR (84.8). It’s hard to find a top-10 list that doesn’t include the Hall of Fame player that played three different infield positions.

The stats might tell you that Anson was the best to ever wear the uniform, but the game was too different at the time. Anson did have a legendary career with the Chicago Cubs, but there are a few players that simply mattered more to the franchise.

7. Greg Maddux

Greg Maddux is arguably the best player to ever put on a Cubs uniform, but some of his best work was done with the Atlanta Braves. Still, the “Mad-Dog” checks in at number seven on this list.

Maddux spent just 10 of his 23 seasons with the Chicago Cubs, and you won’t see his name in the top-10 in all-time Cubs stats leaders. Still, Maddux was an 8x All-Star, 4x Cy Young winner, 18x Gold Glover winner, and won the ERA title four times during his career.

He won his first of four-straight CY Young Awards in 1992, and had 47 complete games with the Cubs in 10 seasons. Maddux received 97 percent of the vote in his first time on the Hall of Fame ballot.

Maddux is wearing a Braves cap in Cooperstown, but Cubs fans consider him one of their own. Watching Maddux carve up opposing lineups will never get old.

6. Ron Santo

Your grandparents might tell you that Ron Santo was their favorite player, and others will tell you about his work on Cubs radio broadcasts. Santo is beloved by Cubs fans, and he is the sixth-best player in Cubs history.

The Hall of Fame third baseman was a nine-time All-Star as a member of the Chicago Cubs and also won five Gold Glove Awards. Santo ranks second in Cubs history with a positional player WAR of 72.1

Santo collected 2,171 hits as a member of the Chicago Cubs and his 337 home runs are fourth-most in team history. Unfortunately for Santo and his teammates, the Cubs never made the playoffs during his career.

His number is retired with the Chicago Cubs, an honor that will become a theme with some other names coming up on the list. Santo was beloved for a reason, as he was one of the best to ever play at the “Hot Corner.”

5. Sammy Sosa

Let’s get this out of the way right now: Sammy Sosa “allegedly” used performance-enhancing drugs, and was also caught using a corked bat. “Slammin’ Sammy” was still one of the best players to ever play in Chicago, and was the best player in baseball for a short period of time.

Sosa is the Cubs’ all-time leader in home runs with 545 blasts, a majority of which traveled onto Waveland Avenue. Sosa ranks in the top-10 in several other statistical categories, and his love for the game and for the city of Chicago was second to none.

The slugger hit at least 49 home runs in each season from 1998-2002 and blasted 66 long balls and drove in 158 runs en route to a league MVP Award in 1998. His home run chase with Mark McGwire saved the game of baseball, and it turned the fortunes of the franchise around.

Sosa’s career with the Cubs ended on a bad note, and he still has not been forgiven by the organization. This man deserves to have his number retired by the team, and he deserves to be honored as the true legend that he was.

4. Fergie Jenkins

Hall of Fame pitcher Fergie Jenkins spent 10 seasons with the Chicago Cubs and is the best pitcher in team history. Jenkins bounced around a ton throughout his career, but his best work came with the Cubs.

Jenkins won the Cy Young Award in 1971, a season in which he completed 30 of his 39 starts that season. The right hander went 167-132 as a member of the Cubs, and had a 3.20 earned run average.

Fergie was inducted into the Hall of Fame in 1991 and has his jersey number retired by the Cubs. The Cubs have had some terrific starting pitchers toe the rubber at Wrigley Field, but Fergie Jenkins was the best.

3. Billy Williams

“Sweet Swingin” Billy Williams checks in at number three on the list, and his offense did all of the talking. The Hall of Fame outfielder posted some huge offensive numbers as a member of the Cubs during his 16-year stint with the team.

Williams had 881 extra-base hits as a member of the Cubs, which is second all-time. The left-handed slugger is also high on plenty of other offensive lists and was Rookie of the Year in 1961.

In his 16 years with the Cubs, Williams posted a .296 batting average with 392 home runs and 1,353 runs batted in. Williams might not have had monster offensive seasons during his career, but he was extremely consistent and a leader in the clubhouse.

The sweet swing of Billy Williams is hard to ignore and was hard for opposing pitchers to figure out. Williams remains a fan-favorite in Chicago and is one of the few remaining players from the famed 1969 team.

2. Ryne Sandberg

Second baseman Ryne Sandberg was traded to the Chicago Cubs after playing just 13 games with the Philadelphia Phillies, and he ended up becoming a legend in the Windy City. In 15 season with the Chicago Cubs, Sanberg was a 10x All-Star, 9x Gold Glove winner, 7x Silver Slugger, and was MVP of the National League in 1984.

“Ryno” is widely considered one of the best second basemen of all-time, and was inducted into the Baseball Hall of Fame in 2005. His famous number “23” is retired by the Chicago Cubs, and he remains one of the most popular players in franchise history.

Sandberg is in the top-5 in a number of offensive and defensive categories with the Chicago Cubs, and he was a constant force in the middle of the lineup. Ryno was one of the best to ever do it at second base, and Cubs fans got to watch it take place in the Friendly Confines.

1. Ernie Banks

Many players on this list could be shuffled around or replaced, but naming the best player in Chicago Cubs history was an easy choice. Ernie Banks, “Mr. Cub” is the greatest player to ever suit up for the team, and the numbers speak for themselves.

The Hall of Fame infielder played all 19 of his seasons with the Chicago Cubs and was an All-Star 14 times during his career. Banks won back-to-back MVP Awards in 1958 and 1959 and is one of the best players in Major League history as well.

Banks played in 2,528 games with the Cubs, which is the most all-time. Number 14 also holds the franchise record for most at-bats, most plate appearances, most total bases, and most extra-base hits.

The only knock on his career was that he never played in the postseason, but Banks always did his part. When you think of the Chicago Cubs, Mr. Cub should be the first thing that comes to mind.

Share on facebook Facebook Share on twitter Twitter

To Top