The Chicago Cubs have won more games than any other franchise in baseball history with the exception of the Giants. Their all-time franchise winning percentage is surpassed in the NL by just the Giants, Dodgers, and Cardinals. However, fans of the team are unlikely to take comfort in that fact, since they have been waiting for more than 90 years for a World Series title and 55 years for a World Series appearance.
The Chicago National League franchise was known as the White Stockings, Colts, and the Orphans before settling in as the Cubs in 1903. They won the very first NL pennant in 1876, and under Adrian "Cap" Anson they won five NL titles in the 1880s. In the first decade of the 20th century the Cubs were the best team in baseball, winning a record 116 games in 1906, 107 games in 1907, 99 games in 1908, and 104 games in 1909 and 1910. In four of those seasons the Cubs won NL pennants, garnering World Titles in 1907 and 1908. Cub faithful are still waiting for their next World Championship. Mainstays on the early 1900s Cubs were Three Finger Brown, Ed Reulbach, Frank Chance, Johnny Evers, Joe Tinker, Frank Schulte, and Jimmy Sheckard. Under the guidance of first baseman Chance, they continued to contend well into the 1910s.
The threat posed by the Federal League from 1913-1915 had a great impact on Chicago. The Federal League Whales were not only popular, they outdrew the WHite Sox and Cubs. When the league was disbanded, the Whales owner, Charles Weegham, was given the option of buying the Cubs, which he did. As a result, the team moved into Weegham's ballpark, which fans know today as Wrigley Field. 1918, a young Cubs' team, built around pitchers Hippo Vaughn, Lefty Tyler, and Claude Hendrix, grabbed the NL flag but were beaten in the World Series by the Babe Ruth-led Red Sox.
The 1920s saw six different managers for the Cubs, and not surprisingly they produced mixed results. But in 1929, due in large part to newly acquired Rogers Hornsby, the Cubs won the pennant with 98 victories. It was the first of four pennants that occurred in three year intervals: 1929, 1932, 1935, 1938. Unfortunately, the Cubs lost the World Series every time. Hack Wilson, Kiki Cuyler, Charlie Grimm, Billy Herman, Gabby Hartnett, Stan Hack, Billy Jurges, Phil Cavarretta, Riggs Stephenson, Lon Warneke, and Bill Lee formed the core of those pennant winning Cubs ball clubs.
By 1945, Grimm was managing the team and Chicago won a tight race for the flag over the favored Cardinals. Their loss in the 7th game of that World Series is the franchise's last appearance in the Fall Classic. After a third place finish in 1946, the Cubs finished in 5th place or lower for the next twenty seasons! Only the great performance of Ernie Banks gave Cubs fans any reason to smile during those years.
By 1969, manager Leo Durocher had assembled a talented Cub team led by Ron Santo, Billy Williams, Ferguson Jenkins, Don Kessinger, Banks, Ken Holtzman, and Randy Hundley. But the Miracle Mets squeezed by the Cubs late in the season, winning the NL East. The Cubs have rarely been so close to the Series since.
The 1970s brought continued disappointment despite the efforts of Bill Madlock, Manny Trillo, Rick Reuschel, Bill Buckner, and Dave Kingman. In the 1980s the Cubs slowly gathered a group of players that exploded in 1984 to win 96 games ? a 25-game improvement over the previous year. Favored to win the pennant, the Cubbies stuck to their losing form and squandered a 2-0 lead against the Padres in the NLCS, losing in Game Five. Once again, the Cubs had failed to end their World Series drought.
The best player on the Cubs in the 1980s was Ryne Sandberg, a slick second baseman who won the 1984 MVP award and plugged the middle infield spot for Chicago for 15 seasons. Outfielder Andre Dawson added fire to the Cub attack in the late 1980s, helping the team win a division title in 1989, only to succumb to the Giants in the playoffs.
The next eight years brought seven losing seasons, before the team revived in 1998 to win a wildcard spot. They quickly exited, leaving Sammy Sosa's home run accomplishments and the play of Mark Grace as the best things to happen to the franchise in the decade. Five seasons later, the Cubs won an improbable division title, improving by 21 games under manager Dusty Baker. Sosa was still slugging homers, supported by a talented young pitching trio of Kerry Wood, Mark Prior, and Matt Clement.
--TheBaseballPage.com
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