The All Time Greatest Chicago Cubs Team

Chicago Cubs (1870-present)

Also known as the White Stockings and Colts

National Association of Professional Baseball Players (1871, 1874-1875)

National League (1876-Present)

National League Pennant 1876, 1880, 1881, 1882, 1885, 1886, 1906, 1907, 1908, 1910, 1918, 1929, 1932, 1935, 1938, 1945, 2016

World Series Champion 1907, 1908, 2016

To the modern sports fan the Chicago National League franchise has been hapless forever. The sports world celebrated enthusiastically when the Cubs finally won in 2016. That was their first National League crown since 1945, and first World Series title since 1908! What is not remembered is that up until 1945 Chicago was the most successful of all the National League Clubs. In the first eight decades after the establishment of the National League, Chicago had won pennants in seven different decades, missing out only in the 1890s. They won 16 NL Championships between the League’s first year (1876) and 1945. That is more than any other franchise up through 1945. Not only did they win more championships than any other club, but they had some of the greatest dynasties in baseball history. Between 1880 and 1886 the Cap Anson Chicago White Stockings won the National League five times. Many consider the 1880s Chicago club the greatest team in the 19th Century but that team would be eclipsed by the juggernaut put together by Frank Selee and managed by Frank Chance 20 years later. From 1906 to 1910 the Chicago Cubs had the best record in baseball history. They went 116-36 in 1906. This is a better record than the 1927 Yankees (110-44), or the 1932 Yankees (107-47) or anybody else, simply the best one year record in the modern era. Their two year record from 1906-1907 (223-81), is also the best ever, as is their three year record between 1906 and 1908 (322-136). Adding in their second place finish in 1909 (104-49) they have the best four year record of all time, and then won another National League pennant in 1910 (104-50) giving them the best five year record in history.

Think of all the great teams in baseball history; the 1926-1928 Yankees, the 1929-1931 Philadelphia Athletics, the 1936-1939 Yankees, the 1942-1946 St. Louis Cardinals, the 1949-1953 Yankees, the 1969-1971 Baltimore Orioles, the 1975-1976 Cincinnati Reds, or the 1998-2001 Yankees. The Cubs had a better record than all those teams. So why aren’t they on the short list of greatest team of all time? Well, despite having the best record in history during the regular season in 1906 they lost the World Series to their cross town rivals the Chicago White Sox in the biggest upset in World Series history. That loss was monumental in how they are perceived today, because they would win the Series easily in 1907 and 1908 over Ty Cobb’s Detroit Tigers, but finished second to the Pirates in 1909, then lose another World Series in 1910. This means they only won two Championships in an otherwise unprecedented five year stretch. That loss to the White Sox is the answer.

Here is our All-Time Greatest Line-up of Chicago Cubs


It’s not close, Charles “Gabby” Hartnett (1922-1940) by a wide margin.

UNDATED: Charles “Gabby” Hartnett of the Chicago Cub poses before a season game. Charles Hartnett played for the Chicago Cubs from 1922-1941. (Photo by National Baseball Hall of Fame Library/MLB Photos via Getty Images)

First Base

Frank Chance (1898-1912) is in the Hall of Fame. Known as “The Peerless Leader” he was one of the mainstays of  Chicago’s greatest teams from 1906-1910, yet he is the second best first baseman in Chicago history behind the “Marshalltown Infant”  Adrian “Cap” Anson (1876-1897). The first baseball “Superstar”, the first man to collect 3,000 career hits and probably the greatest player in 19th century baseball. Anson was a larger than life figure in the early years of the National Pastime. We wrote a Stories You Should Know on him here.

Second Base

Not much argument here, Ryne Sandberg (1981-1997) by a hefty margin over another member of the Cub’s 1906-1910 juggernauts, Johnny Evers (1902-1913). Sandberg was a 10 time All-Star, won the Gold Glove at second base in nine seasons and the NL MVP in 1984, culminating in his election into the Hall of Fame in 2005. One of the 10 greatest second baseman of all time.

Third Base

A close call between Stan Hack (1932-1947) and Ron Santo (1960-1973). Hack was the games best lead-off man and a good third baseman. Probably the best player on Chicago’s 1938 NL Championship team. Hack was a fine player, however,  with one big reservation, we give a slight edge to Santo. Santo was a devastating offensive player in the run scarce 1960s. Hitting over 30 home runs four times, driving in more than 90 runs eight times, leading the league in walks four times, while also being a five time Gold Glove at third base. The one big concern? That despite the presence of two other Hall of Famers in their everyday line up (Ernie Banks, and Billy Williams), Santo, unlike Hack, never won a NL Pennant during his 14 years with the Cubs.


Joe Tinker was the shortstop on the famous Tinker to Evers to Chance double play combination that was the guts of the Cubs best teams. Despite that he is the second best shortstop in team history. The best by a wide margin, even though he played more games at first base than shortstop during his Chicago career, is Mr. Cub himself Ernie Banks (1953-1971).

Left Field

Considering the long history of baseball in Chicago it’s surprising how unimpressive their best outfielders are. Billy Williams (1959-1974) is the best outfielder in Cub history. This is not a knock on Williams, after all he’s in the Hall of Fame, but he’s an extremely weak best outfielder. Look at the other franchises that started in the 19th Century, their best outfielders are far superior; The Giants (Willie Mays, Mel Ott, Barry Bonds), Braves (Henry Aaron), Cardinals (Stan Musial), Dodgers (Duke Snider), Cincinnati (Frank Robinson), Pittsburgh (Paul Waner, Roberto Clemente), Phillies (Ed Delahanty). Williams is out of place on that list.

Center Field

Hack Wilson holds one of the most iconic records in baseball history, driving in 191 runs in 1930 while playing center field for the Cubs. He also had a big year in 1929 when the Cubs won their only NL Pennant in the 1920s, but 1930 was his last big year for Chicago. We think Jimmy Ryan (1885-1889, 1891-1900) was better. Ryan, who was the starting pitcher in game five of the 1886 World Championship Series between Chicago and St. Louis, was the best player on the Cub’s team in the late 1880s, then came back in 1891 as a mainstay in the outfield. Jimmy Ryan (1885-1889, 1891-1900) in a close call over Wilson.

Right Field

Hack Wilson can also be considered as a right fielder, butFrank “Wildfire” Schulte (1904-1916) was a more valuable player in Chicago than was Hack. Schulte was another memberof the Cub’s best teams, he won the Chalmers Award as the NL MVP in 1911, and was a Cub regular in the outfield for 12 of his 13 years.The only thing left to decide is what to do with the disgraced Sammy Sosa (1992-2004). Sosa was clearly a more productive player than Schulte. He also won a MVP Award while patrolling the Chicago outfield. The problem with choosing Sosa? He was also caught in two serious cheating scandals, using a corked bat and injecting himself with Performance Enhancing Drugs. We, from the beginning, said that performance on the field is what we were judging, so we’ll hold our noses and choose the cheater, Sammy Sosa (1992-2004).

4 Oct 2003: Sammy Sosa of the Chicago Cubs during the Cubs 3-1 victory over the Atlanta Braves in game 3 of the NLDS at Wrigley Field in Chicago, IL. Mandatory Credit: Dilip Vishwanat/Sporting News/Icon SMI


With apologies to Christy Mathewson, the best pitcher in the National League from 1906 to 1910 was Chicago’s Mordicai “Three Finger” Brown (1904-1912). In that five year period Brown went 26-6, 20-6, 29-9, 27-9, and 25-14 with ERA’s between 1.04 and 1.86. Brown is the clear #1 starter.

After Brown it gets murkier, but we’ll go with Ferguson Jenkins (1967-1973, 1982-1983) as the #2. Fergie won 20 games six years in a row for the Cubbies between 1967 and 1972 and was elected to the Hall of Fame in 1991.

The #3 Man is the “Great Alex”, Grover Cleveland “Pete” Alexander (1918-1926). Pete’s best years were with the Phillies, then was traded to the Cubs after the 1917 season. He would be drafted into the U.S. Army and serve in France with the 342nd Field Artillery during WWI, be exposed to mustard gas while serving, causing many life changing health issues. When he was finally back to good health in 1920 he won the pitching triple crown for the Cubs (leading the league in wins, ERA and strikeouts). That would be Pete’s last great year, but he gave Chicago five more solid season before being dealt to the St. Louis Cardinals in 1926, where he would find lasting fame in the 1926 World Series.  

#4 Clark Griffith (1893-1900) is best remembered today as the Owner and Manager of the Washington Senators. What is largely forgotten is that he was quite a pitcher for Cap Anson in the 1890s. His defection to the upstart American League was one of the key events that secured the success of the new league. His record in Chicago was 152-96, at a time that the “Cubbies” were getting tired of Anson and falling out of contention.


Chicago has had a good share of Hall of Fame Managers. Frank Selee from 1902-1905, Joe McCarthy from 1926-1930 and Leo Durocher from 1966-1972, but the selection of their best manager comes down to the same two men who we considered at first base. Adrian “Cap” Anson (1879-1897) managed the White Stockings to five championships in the 1880s. In two of those years (1885,1886) they would compete in the original World Championship Series against the American Association’s St. Louis Browns. 1885 would end in a confusing tie and 1886 in a controversial 4-2 loss. Frank Chance (1905-1912) managed Chicago’s greatest team. They would win four pennants and two World Series titles during his tenure. In 1906 the Cubs had the most wins in the history of the National League, and as noted earlier Chicago would have a higher winning percentage than any other team in history during Chance’s eight year reign. Despite Chance’s unprecedented record, we’ll again go with Anson over Chance. The big difference between the two is that Anson was solely responsible for putting together his championship teams, while Chance largely inherited his squad from Frank Selee.


This choice is complicated, but seems to sort itself out logically. Let’s start with the player most modern fans would choose as the greatest Cub, Ernie Banks. Banks was the first player to win back to back MVP Awards, winning them in 1958 and 1959. He was also the first man to win the MVP playing for a team with a losing record (the Cubs had a losing record in both his MVP seasons), and there lies the problem. If Banks was so good, how come his team didn’t win. In the 1960s Banks moved to first base due to injuries, but was joined by two other Cub greats in the line up (Ron Santo and Billy Williams). They still didn’t win. We think this alone eliminates all three as the greatest Cub. Ryne Sandberg has a similar problem. As good as he was, the Cubs won no pennants in his entire 16 year stint in Chicago. This leaves three contenders; “Three Finger” Brown, Gabby Hartnett, and Cap Anson. Brown was the best player on the Cubs best teams (1906-1910), but he had a Hall of Fame double play combination to back him up. He would be a reasonable choice, but we think he ranks behind the other two. Hartnett is consistently rated in the top ten of all time catchers, we think he’s a little underrated. Hartnett has no negatives. An A+ defensive player who hit like an outfielder, the National League MVP in 1935, most famous today for his “Homer in the Gloamin’” that clinched the pennant on the final day of the 1938 season. 1938 was the 4th time Hartnett led the Cubs into the World Series (they lost each time). So it comes down to Hartnett vs Anson. Cap Anson was the dominant figure in 19th century baseball. He was the best player on six National League Champion Teams, managed them in five of those seasons. He was the only man to amass 3,000 hits during the 19th century. Not a popular figure to modern day writers due to his stance on race, which was by modern day standards appalling, but it’s undeniable he had a tremendous impact on Chicago baseball. In a decision that the old Captain would undoubtedly agree with, we feel that Adrian “Cap” Anson is the greatest Cub of all time.


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