For more than 100 years, the Chicago Cubs were not a respected franchise. In fact, they spent more time as the butt of jokes around the league. The Chicago team changed its name to the Cubs in 1903, and they won back-to-back World Series in 1907 and 1908. It looked like this would be one of the great franchises in baseball.
Whether it was a billy goat, a black cat, a Gatorade glove, or Steve Bartman, the Cubs have more curses than World Series titles. They were stuck on those two until the turn of the century. Finally, in 2016, the Cubs broke the curse.
However, despite the broken seal of a title, there were dozens of all-time greats who spent time in Chicago’s North Side. Wrigley Field is legendary because of the men who took the field there. That’s why many of the more recent Cubs, including some of the stars on that 2016 team, didn’t make the cut for the All-Time lineup. So, who did make the cut?
First Base
Mark Grace
1988-2000
Mark Grace is still one of the most underrated players of his era. He has a ton of hits and played incredibly well for the Chicago Cubs during an era fans aren’t exactly celebrating. Grace joined the Cubs in 1988 as a rookie, and he finished second in National League Rookie of the Year voting. He had a consistent statline basically until he went to Arizona in 2001.
Grace was very reliable to play 90 percent of the season, and he was good for a batting average between .295 and .330. He would get home runs here and there, but he never hit 20 in a season in his career. He was a guy who was getting on base with consistency. He finished three different seasons with a .400 on-base percentage or higher.
Grace finished his Cubs career as a three-time All-Star and a four-time Gold Glove winner. He was the epitome of a fan favorite. He was on a team that desperately needed what he brought to the table. He was selfless and put the ball where it needed to go at the time. In his 13 years in Chicago, he only went to the postseason twice. The first time he was there, he did everything he could to get them past the first round. He hit .647 for the series (11 for 17), and he added three doubles, a triple, and a home run. Grace had eight RBIs in five games, but it wasn’t enough to keep them going towards a World Series title.
Second Base
Ryne Sandberg
1982-1997
Ryne Sandberg is another player who is underrated, but unlike Grace, that has come with time. During his era, Sandberg was considered one of the best second basemen in the history of the baseball.
Sandberg led all of baseball in home runs. That was unheard of from a second baseman. He hit 40 homers in 1990. Nobody displayed power at that position. He’s one of 10 players to win MVP at second base, taking home the trophy in 1984 after recording 200 hits, a .314 batting average, 19 home runs, 84 RBIs, and a league-leading 19 triples. Sandberg added 32 steals (which jumped to 52 stolen bases the next season), which helped his MVP case.
Like Grace, Sandberg didn’t get to show his value to the league on the biggest stage. He only played in 10 postseason games in his career, which was entirely played with the Cubs. He did hit .385 during those 10 games. We would have loved to pick someone who had a long history of postseason glory, but there’s not a lot of that in Chicago, and there’s no way this list would have validity if it didn’t include Sandberg in some capacity.
Short Stop
Ernie Banks
1953-1971
Ernie Banks is often considered the best Chicago Cubs player of all time. Banks started his career playing in the Negro Leagues, but he joined the Cubs in 1953. He immediately made an impact, coming in second for Rookie of the Year in 1954. He would go on to be a 14-time All-Star and two-time MVP. What’s even more impressive was Banks won those MVPs while the Cubs finished both those seasons as fifth-place finishers. It’s hard to deny a guy playing in the 1950s National League who hits a combined 92 home runs and 272 RBIs over those two seasons.
He finished as a member of the 500 Home Run Club, a Gold Glove winner, and a first-ballot Hall of Famer. Banks is the Pride of the Chicago Cubs. He is everything we want players to emulate today. He used his speed and power exactly to his advantage in the batter’s box, and he made it a point to do everything the Cubs needed to win games. It didn’t always work out in his favor, and Banks definitely deserved more, but fans will remember the heroics and his loyalty most of all.
Of course, as Banks got older, he started to fall off. He was moved to first base to make up for his lack of mobility, and his hitting had become a little more inconsistent. He was still a good player, and he was eventually named a player-coach towards the end of his career.
Third Base
Ron Santo
1960-1973
There are few people who have a solid lock on the top spot at a position than Ron Santo had at third base for the Cubs. There is no player who is particularly close in the history of the Cubs. Meanwhile, Santo was a devastating player in the box. He crushed 30+ home runs for four consecutive seasons from 1964 to 1967. Santo was fantastic in the batter’s box and in the field, finishing his career as a five-time Gold Glove Award winner. There’s nothing Santo couldn’t do to help the Cubs.
Santo was a nine-time All-Star and finished in the top five in National League MVP Award balloting twice. His final stat line was amazing for his era (337 homers, 353 doubles, 1,290 RBIs, 1,109 runs scored, and 2,171 hits). He was also way ahead of his time, prioritizing getting on base before it was cool to do so. Santo led the NL in walks four times in his career.
Santo even led the NL in WAR in 1967. His ridiculous 9.8 WAR didn’t even warrant him an All-Star nod. It shows the disrespect for the Cubs' talent during this time. While the Yankees and Dodgers got all the credit, the Cubs were putting out stars. Santo also did well to help the Cubs have a force in the lineup while Ernie Banks saw his star diminish. It was a great passing of the torch at Wrigley Field.
Catcher
Gabby Hartnett
1922-1940
The man behind the “Homer in the Gloamin” is also the best catcher in Chicago Cubs history. Gabby Hartnett was amazing for the Cubs in the 1920s and 1930s. He has all the accolades. He was a six-time All-Star and was elected to the Hall of Fame in 1955. He played more than 1,700 games at catcher, which is a grind in of itself. Only 14 players in the history of baseball have played more games at the catcher position than Hartnett.
His best season came in 1935, when he won his only NL MVP. He became this insanely proficient hitter that season. He sacrificed power for impact, hitting .344 and slugging just 13 home runs but still getting 91 RBIs. He had a .404 on-base percentage, giving the lineup around him more and more chances to deliver. That’s an interesting MVP case, but it was clear it was one of his most impactful seasons since he had his third-highest career WAR that season at 4.9.
The difference between Hartnett and some of the others on this list is that Hartnett had plenty of opportunities to deliver in the playoffs. He’s played in the World Series on four different occasions (although he lost every time). He wasn’t great in the championship series, putting up just three RBIs in 54 World Series at-bats, but he did get plenty of hits in the 1932 and 1935 World Series.
Right Field
Sammy Sosa
1992-2004
Sammy Sosa will always be a controversial figure when it comes to the history of baseball. He was someone who was watching his career go down as a member of the Chicago White Sox. He went across town, and Sosa revitalized his career. Yes, there are some extracurriculars that helped him along the way, but the impact Sosa had on baseball in the late 1990s is impossible to ignore on this list.
Sosa was one of the best players in the league for close to a decade. His home run chase with Mark McGwire in 1998 saved baseball. The sport was getting some juice from a New York Yankees dynasty that got them past the 1994 players’ strike, but it was the home run chase that pulled them out of it. ESPN would cut out of current programming to see Sosa at bats in 1998. He finished the season with 66 home runs and won the MVP that season.
He passed Ernie Banks for most home runs as a member of the Cubs with 545. He trails Banks in RBIs (and technically Cap Anson, but he was playing for the Chicago White Stockings) with 1,414. He had 873 extra base hits, trailing Banks and Billy Williams. Sosa led the NL in runs three times, home runs two times, and RBIs twice as well. Sosa was a fantastic player, even considering how he became an all-timer.
Center Field
Hack Wilson
1926-1931
When looking at unbeatable records, many point to Cy Young’s 511 wins and Joe DiMaggio’s 56-game hitting streak, but not many point to Hack Wilson’s 191 RBIs in 1930. It’s an MLB record that hasn’t been touched. The closest anyone has gotten to it in 75 years is Manny Ramirez putting up 165 RBIs in 1999. In the 21st century, Sosa’s 160 in 2001 was the closest anyone got. That’s still 31 RBIs away from the record. Wilson wasn’t with the Cubs very long, but he was incredible when he was there.
From 1926 until 1930, Wilson never had a WAR less than 5.0. He led the league in home runs in four of those five seasons. He was the best player in baseball at the time. He dominated at the plate, hitting for power unlike anyone in the league at the time.
Wilson was not built like your typical athlete, and he probably wouldn’t have even been given the opportunity to play today. He stood at just 5’6 and had a big belly. He broke his leg when coming up while playing in Martinsburg, West Virginia, which forced him to move from catcher to center field. He also had a big fight with alcoholism, which is why his star only shone for five seasons. If he had a different journey, Wilson might be in the same conversation with the game’s best of all time, but he’ll have to settle for center field on the all-time Cubs lineup.
Left Field
Billy Williams
1959-1974
Billy Williams is one of the best left-handed hitters of his era. He played 16 of his 18 seasons with the Cubs, and he is all over their “all-time” list. Consistency was key for Williams, who once played more than 1,100 games in a row and had 20 or more home runs for 13-straight seasons. That’s how he accumulated so many great numbers, including more than 400 home runs and missing 3,000 hits by about two seasons.
Williams is the quintessential “play the game the right way” player. There wasn’t a lot of flash to his game, but fans and his teammates knew that he was going to do exactly what he was supposed to do when he was in the outfield and in the batter’s box. Consistency was key. Nobody was complaining about Williams. He did what he needed to do to contribute for the Cubs.
It’s unfortunate that Williams was never able to get the right pieces around him to get the Cubs to the World Series. He didn’t play in the playoffs until he joined the Athletics when he was 37 years old. He also just missed out on the MVP award in 1970, coming in second despite leading all of baseball in hits and runs.
Designated Hitter
Kris Bryant
2015-2021
It was incredibly hard to keep Andre Dawson off this list, but we can’t ignore the sheer impact Kris Bryant had on the Cubs in his time there. Some might be looking at his career a little differently with how he’s struggled with the Colorado Rockies, but he was undeniable with the Cubs.
Bryant started his career off with a bang, quite literally. He won the Rookie of the Year in his first season, putting up 26 home runs and 99 RBIs upon his arrival in 2015. The very next year of his career, Bryant won the NL MVP. He finished the year with 39 home runs and 102 RBIs. He also led the NL in runs and WAR, and he was named to his second of four All-Star teams.
Bryant was a huge proponent for the Cubs in ending their curse and finally winning the World Series in 2016. He hit over .300 for the playoffs and added five doubles and three home runs. He added nine walks in 17 games, showing how he was becoming one of the smartest players in the game. It was a perfect season from Bryant. His success was relatively short, as he was traded to the San Francisco Giants in 2021, but that six-year run is as good as the Cubs have seen in a long time, and it led to a World Series title.
Starting Pitcher
Fergie Jenkins
1966-1973, 1982-1983
There are so many creative places we could go with the Cubs starting pitcher. Do we want to prioritize top-level play, like Mark Prior and Kerry Wood in 2003? Could we go with the best pitcher who played with the Cubs (Greg Maddux)? We went with the best of all worlds. Ferguson Jenkins, best known as Fergie, was a really good pitcher for the Cubs in the late 60s and early 70s.
Jenkins was an absolute workhorse. He led the league in starts three times while with the Cubs, and he was the complete games leader for all of baseball three times, as well. He won the NL Cy Young in 1971, leading the league in innings pitched and walks per nine. He had more than seven strikeouts for every walk he gave up. Jenkins was dominant with amazing control.
It’s funny how the Cubs actually saved his career by taking him out of the bullpen. He struggled with the Philadelphia Phillies before the Cubs took him on based on talent and got themselves a star. His superstar performance came at the 1967 All-Star Game, when he dominated an American League lineup with the best of the best of all time, including Mickey Mantle, Harmon Killebrew, and Rod Carew. He’s also the first Canadian to win the Cy Young.
Relief Pitcher
Lee Smith
1980-1987
While starting pitcher is not an easy one to pick for the Cubs, relief pitcher is probably the easiest choice on this list. Lee Smith was one of the best relief pitchers in the history of baseball. He had the league lead in saves all-time for a long time until Trevor Hoffman and, eventually, Mariano Rivera passed him. Smith is still third all-time at the time of this writing with 478 saves.
For the first eight seasons of Smith’s career, he ended games for the Chicago Cubs. He led the league in saves with 29 in 1983, and he ended up ninth in Cy Young voting that season. Smith was often asked to pitch in different situations, as managers didn’t just save their closers for save situations in the 1980s. He was coming in for multiple-inning performances often.
Ironically, Smith almost left baseball when the Cubs said he wasn’t a starter. Luckily for everyone, he stuck it out. The towering pitcher (he stood at 6’5) would intimidate his opponents just with his stature. Then, he would throw a rocket of a fastball past hitters. The Cubs' inability to win ended the Smith tenure in Chicago. They traded him to Boston, and he went on to continue his stellar career in other cities. However, his biggest impact came in the Windy City.