The Chicago Cubs are by far one of the most storied franchises in all of baseball. The franchise was founded in 1876, but they were referred to as the White Stockings, then the Colts, and finally the Orphans before their current name was introduced in 1902. The current name comes from when a local reporter used the term “Cubs” in an article about the team’s youth. The name stuck and they have been known as the Cubs ever since.
In previous years, an article like this might begin with a knock on the Cubs and how they are in the midst of a 100-plus year World Series drought. Of course, the Cubs put that narrative to bed when they won the 2016 World Series, their first since 1908. While it had looked as if they were building a dynasty, the team ended up trading away many of their star players during the 2021 trade deadline. Hopefully, they will soon have a new crop of players breaking franchise records, but for now, here is Chicago’s best 26-man roster of all time.
Make sure to check out all of our other All-Time Rosters.
Starting Nine
Gabby Hartnett, C
People may forget about Hartnett, which is understandable seeing as he last played for the Cubs in 1940. Nevertheless, he is still the all-time leader for Cubs backstops in runs, hits, doubles, triples, home runs, RBIs, and walks. In his 19 years with the Cubs, Hartnett was a six-time All-Star and the MVP of the 1935 season. Hartnett surely would have had more All-Star appearances, but the inaugural game did not occur until his twelfth season in the league. The Hall of Famer finished his Cubs career slashing .297/.370/.490 with 231 home runs and 1,153 RBIs.
Anthony Rizzo, 1B
Admittedly, Rizzo does not have the best all-around stats out of Cubs’ first baseman. However, he is by far the greatest to ever play the position in Chicago. In early 2012, the Cubs acquired Rizzo from the San Diego Padres in exchange for right-handed pitcher Andrew Cashner. In parts of 10 seasons with the Cubs, Rizzo was a three-time All-Star, four-time Gold Glove winner, one-time Silver Slugger, and one-time Platinum Glove winner. Most notably, Rizzo was the face of the 2016 Cubs team that won the World Series, ending their 108-year championship drought. The Cubs’ all-time leader in home runs at first base, Rizzo slashed .272/.372/.489 during his tenure. On top of that, he was a staple in the Chicago community due to his charitable work.
Ryne Sandberg, 2B
The Cubs acquired their best second baseman of all time in a 1982 preseason trade with the Philadelphia Phillies. Sandberg had a very productive first two seasons in Chicago but truly came into his own during the 1984 season. The Hall of Famer hit .314/.367/.520, along with 32 stolen bases, and a league-best 114 runs scored and 19 triples. To no surprise, he was named the league MVP. In total across 15 years on the Cubs, Sandberg amassed 10 All-Star Games, nine Gold Gloves, seven Silver Sluggers, and of course the 1984 MVP. He had an amazing mix of great speed and great power in Chicago, totaling 282 home runs and 344 stolen bases with the team.
Ron Santo, 3B
The Cubs’ second-highest WAR leader of all time, Santo was a fixture in the Chicago lineup for 14 years. Santo signed with the Cubs in 1959 and later made his debut with the team in 1960. Santo cemented himself as a Cub legend by earning a spot on nine All-Star teams, winning five Gold Gloves, and slashing .279/.366/.472 across 2,126 games. The Hall of Famer added to his legacy by leading the league in walks four times, smashing 337 home runs, and driving in 1,290 runs. Santo was widely considered one of the best at his position during his era, and likewise one of the best Cubs of all time.
Ernie Banks, SS
There is no debate for the best Cubs shortstop of all time. The man famously nicknamed “Mr. Cub” played 19 years in the Major Leagues, all in Chicago. Banks left the Negro Leagues in 1953 to join the Cubs and became the first African American player in team history. Across his Hall of Fame career, Banks was a 14-time All-Star, two-time MVP, and a one-time Gold Glove winner. Winning the award in 1958 and 1959, Banks is just one of thirteen players to ever win back-to-back MVP awards. Banks has the most games played in the history of the Cubs with 2,528, the second-most home runs in club history with 512, and most total bases at 4,706. Mr. Cub concluded his career with a .274/.330/.500 slash line.
Billy Williams, LF
One of the best all-around hitters in franchise history, Williams spent 16 years on the Cubs. In his first full season in 1961, Williams made a tremendous impression by winning Rookie of the Year honors. He was additionally voted to six All-Star teams, won the 1972 batting title, and of course, was voted into the Hall of Fame in 1987. In Chicago, Williams accumulated 2,510 hits, 392 home runs, and hit .296/.364/.503. He twice was the runner-up for the league MVP award and also finished three seasons with over 200 hits. Williams is third all-time in Cubs history with a 64.5 oWAR.
Hack Wilson, CF
Wilson only played six seasons for the Cubs, but it was an extraordinary dominant stretch. From 1926-1931, Wilson patrolled center field for Chicago, but he was best known for his bat. As a Cub, Wilson slashed .322/.412/.590 with 190 home runs and 185 doubles across just 850 games. The National League did not issue an MVP award in 1930 due to financial constraints, but Wilson certainly made a strong case. He slugged 56 home runs, drew 105 walks, slashed .356/.454/.723, and recorded an MLB record 191 RBIs. Wilson led the league in home runs four out of six seasons while in Chicago and also led in RBIs twice. While he only ended up playing 12 seasons in the Major Leagues, his stint on the Cubs was a huge factor in Wilson’s election to the Hall of Fame in 1979.
Sammy Sosa, RF
The best power hitter in franchise history, Sosa came to the Cubs from the Chicago White Sox in a trade before the 1992 season. In his 13 seasons on the Cubs, Sosa was a seven-time All-Star, six-time Silver Slugger, and the MVP of the 1998 season. His historic 1998 season was a part of the legendary home run race between himself and Mark McGwire of the St. Louis Cardinals. Sosa clubbed 545 home runs, drove in 1,414 runs, and slashed .284/.358/.569 during his time as a Cub. Based on these stats alone, Sosa should be a Hall of Famer. However, his questionable link to PED usage in the early 2000s has led voters to leave him off the ballot. Nevertheless, this does not take away from the fact that Sosa is the best right fielder in franchise history.
Andre Dawson, DH
Dawson gets the nod as the designated hitter due to his stellar six-year stint with the club. At 32 years old, Dawson joined the Cubs via free agency before the 1987 season. He made a tremendous first impression in 1987, winning the league MVP, a Gold Glove, a Silver Slugger, and an All-Star appearance. In total, Dawson was a five-time All-Star, two-time Gold Glove winner, and a one-time Silver Slugger recipient during his tenure in Chicago. The Hall of Famer hit .285/.327/.507, drove in 587 runs, and smashed 174 home runs as a Cub.
Starting Rotation
Fergie Jenkins RHP
The franchise leader in pitching WAR, Jenkins is without a doubt the best starter in Cub history. Jenkins came to Chicago via a trade with the Phillies during the 1966 season. During 10 seasons in Chicago, he was named to three All-Star teams and was the winner of the 1971 Cy Young Award. In this magnificent Cy Young campaign, Jenkins went 24-13, threw 30 complete games, and posted a 2.77 ERA. Across two separate stints with the Cubs, Jenkins compiled a 3.20 ERA, a 167-132 record, and 2,038 strikeouts. The Hall of Famer also led the league in games started three times and complete games three times while playing for the Cubs.
Mordecai Brown, RHP
Brown was best known for the insane movement that he was able to harness on his pitches. The reason behind this of course is that Brown lost part of his right index finger in a farming accident as a child. Although he began his career with St. Louis, he was traded to the Cubs before the 1904 campaign. In parts of 10 seasons with Chicago, Brown compiled a record of 188-86, logged 2,329 innings, and posted just a 1.80 ERA. Brown appeared in four World Series for the Cubs between 1906-1910, winning two of them. In these games, the Hall of Famer threw 57 ⅔ and pitched to a 2.97 ERA. To this day Brown is still the franchise leader in shutouts and WHIP.
Hippo Vaughn, LHP
Vaughn easily has been the best left-handed pitcher to pitch for an extended period with the Cubs. Vaughn is the club’s leader in WAR, wins, games started, complete games, strikeouts, and innings for a left-handed starting pitcher. After stints with the New York Highlanders and the Washington Senators, Vaughn was sent to Chicago for the 1913 season. He went on to pitch nine seasons with the Cubs, posting a 151-105 record with a 2.33 ERA over 2,216 ⅓ innings. Vaughn ended up winning the National League triple crown in 1918 by leading the league in wins, ERA, and strikeouts.
Greg Maddux, RHP
Maddux may best be remembered by his time on the Atlanta Braves, but he did pitch parts of 10 seasons in Chicago. The Cubs drafted Maddux in the second round of the 1984 draft and he was already pitching in the majors by 1986. The Hall of Famer would end up winning 133 games, striking out 1,305 batters, and totaling a 33.7 WAR while with the Cubs. This included five Gold Gloves, two All-Star appearances, and the 1992 Cy Young Award for the ballclub. Maddux additionally famously returned to play for the Cubs after 11 years on the Braves, winning his 300th game and getting his 3,000th strikeout with the team that drafted him.
Jon Lester, LHP
In parts of six seasons with the Cubs, Lester logged 1,002 ⅔ innings, struck out 940 batters, had an ERA of 3.64, and a record of 77-44. Similar to the case for Rizzo, Lester may not have had as great cumulative stats as some other pitchers, but his time in Chicago meant much more to the franchise. The Cubs went out and spent $155 million on Lester before the 2015 season to show the baseball world that they were ready to compete. They did just that, winning the 2016 World Series in large part due to Lester’s work on the mound. Lester came in second in Cy Young voting that year, going 19-5 with a 2.44 ERA over 202 ⅔ innings. He was additionally the co-MVP of the 2016 NLCS, appeared in three 2016 World Series games, and was a two-time All-Star on the Cubs.
Bullpen
Lee Smith, RHP (Closer)
Smith is no surprise on this list, seeing as he is one of the top closers in baseball history. The Hall of Famer’s 180 saves as a Cub are the most in franchise history and his 478 career saves are the third-most in MLB history. Chicago drafted Smith as a starter in the 1975 draft but transitioned him to the bullpen by the time he made it to the majors. Smith holds the club record for games finished, is second all-time in reliever strikeouts, and made it to two All-Star Games with the Cubs. He is famous for pitching multiple relief innings per game, tossing 681 ⅓ innings across just 458 games for Chicago.
Bruce Sutter, RHP
Another Hall of Fame closer, Sutter spent his first five seasons in Chicago. During that stretch, he was a four-time All-Star and the winner of the 1979 Cy Young Award. In his Cy Young campaign, he finished 56 games, had a league-best 37 saves, logged 101 ⅓ innings, and finished with a 2.22 ERA. As a Cub, he appeared in 300 games, struck out 494 batters over 493 innings, and posted a 2.39 ERA.
Carlos Marmol, RHP
The club’s all-time leader in strikeouts per nine innings, Marmol was a staple of the late-2000s and early 2010s Chicago bullpens. Marmol ended up pitching in eight seasons for the Cubs. Across these seasons he finished with a 3.50 ERA, 117 saves, and 703 strikeouts in only 542 ⅓ innings. The Dominican Republic native finished a league-best 70 games in 2010 and was also named to the 2008 All-Star Game.
Pedro Strop, RHP
Perhaps the best setup man in the history of the Cubs, Strop was acquired via a trade with the Baltimore Orioles during the 2013 season. He has gone on to pitch in parts of eight seasons with Chicago and holds the franchise record for holds. In 413 games for the Cubs, Strop pitched to a 2.88 ERA with 428 strikeouts over 375 innings. Strop was additionally a part of the 2016 World Series champion team, tossing three scoreless appearances.
Randy Myers, LHP
Myers makes for a perfect left-handed relief option out of this bullpen. He may have only played for the Cubs for three seasons, but he remarkably ranks fourth in team history in saves. Between 1993 and 1995, Myers compiled 112 saves, 150 games finished, and 177 strikeouts across 171 ⅓ innings. He was an All-Star in two of his three seasons in Chicago, but surprisingly not the year he led the league with 53 saves.
Charlie Root, RHP (Swing Man)
Root pitched his final 16 out of 17 professional seasons as a member of the Cubs, spending time in both the bullpen and as a starter. Originally joining the club in 1926, he would go on to win the most games, throw the most innings, and appear in the most games in franchise history. Root finished his Cub career with 605 games played (339 starts), 3,137 ⅓ innings pitched, 171 games finished, and an ERA of 3.55. He pitched in four World Series for the Cubs and was the pitcher on the mound when Babe Ruth of the New York Yankees iconically “called his shot” in the 1932 World Series.
Bench
Mark Grace, 1B
The left-handed-hitting first baseman spent 13 years in a Cubs uniform, beginning his tenure with the ballclub in 1988. He would go on to become a three-time All-Star and four-time Gold Glove winner while in Chicago. In terms of Cubs’ first baseman in the modern era, he is first all-time in hits, runs, doubles, RBIs, and walks. As a Cub, he slashed .308/.386/.455, smacked 456 doubles, and drove in 1,004 runs in 1,910 games.
Kris Bryant, 3B, OF, 1B
Another member of the magical 2016 World Series champion team, Bryant is the only Cub to ever win both the Rookie of the Year and MVP awards. Seeing as Bryant’s MVP season was in 2016, he played a huge role in ending Chicago’s infamous 108-year championship drought. A former number two overall draft pick by the Cubs, Bryant hit .279/.378/.508 with a 27.6 WAR in parts of seven seasons. Before he was traded at the 2021 trade deadline, Bryant was named to four All-Star Games to go along with his major awards.
Bill Nicholson, RF
During his 10 seasons in Chicago, Nicholson proved to be one of the more consistent sluggers of the 1940’s. For the Cubs, the left-handed-hitting slugger ended up belting 205 home runs, smashing 245 doubles, driving in 833 runs, and hitting .272/.368/.471. All of this while sporting a 38.5 WAR. The 1944 campaign was arguably his best in Chicago as he led the league in home runs with 33, RBIs with 122, and runs scored with 116. Nicholson was named to the All-Star Game four times with the Cubs.
Stan Hack, 3B
Hack spent all 16 of his professional years playing third base for the Cubs. He made his Major League debut in 1932 but began to come into his own during the 1934 season. Hack was named to five All-Star Games and led the league in hits and stolen bases twice each. The left-handed hitter excelled in the four World Series he was able to play in. Here he slashed .348/.408/.449 in 18 games. Hack finished his career with 2,193 hits, 1,239 runs scored, a .301/.394/.397 line, and a 55.5 WAR.
Willson Contreras, C
Unlike many of his 2016 World Series champion teammates, Contreras was not traded away at the 2021 trade deadline. Through the 2021 season, the backstop has spent all six years of his career in Chicago. He has been named to two All-Star Games, started 621 games, spent two seasons in the top 10 for defensive WAR in the majors, and has averaged 4.4 WAR per season thus far. Contreras will likely only stick on this list in the future if he stays with the Cubs long term.
Cap Anson, 1B
Purely statistically speaking, a list of Chicago greats would not be complete without Anson. Despite not having played since 1897, his 84.8 WAR throughout 22 seasons with Chicago is still a club record. Anson additionally leads the franchise all-time in hits, singles, doubles, and RBIs. He was baseball’s original superstar throughout the late 1800s, earning him a spot in the Hall of Fame. However, he had well-documented character flaws that severely detract from the ability to praise his work on the field.
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