Led by their first baseman/manager Cap Anson (photo), and their colorful utility man King Kelly (who played every day, but all over the field--every position except pitcher), Chicago was one of the biggest draws in the league. Anson led the league in runs batted in, Kelly led the league in batting average, on-base percentage and runs, and lead off man George Gore was walked more often than any other player.
Chicago was a wide open town in 1886; not to mention the epicenter of the increasingly violent labor movement. On May 4, the Haymarket Riot took place, which took the lives of eleven Chicagoans including seven police officers.
But while Chicago was a violent, scary, and decadent city, it had also fallen in love with it's baseball team.
When they played Detroit with first place at stake, 12,000+ fans came out to see the game (a HUGE crowd in those days). Both teams arrived in spectacular fashion--with a police and fire escort in their horse-drawn carriages. Chicago won the game and moved into first place.
The White Stockings sure loved the spotlight, and they may have loved the nightlife even more. King Kelly in particular was a notorious drunk, and he liked to drag his teammates into the gutter with him. Chicago had one of the most notorious red-light districts in the world at the time (it was the Las Vegas of the 19th century), and that certainly didn't help. One night on the town, a backup outfielder named Billy Sunday could take the debauchery no more, and found the Lord. It got so bad that Chicago owner Albert Spalding hired detectives to follow the players around and began fining them for their drinking. Seven different players were fined $25 each.
But despite their partying ways, Chicago was still the best team in baseball. The regular season came down to the final day. When Chicago beat Boston 12-3, they won the pennant.
They did play in the World Series against the St. Louis Browns after the regular season, but the World Series was really just an exhibition in those days. Nevertheless, it was a high stakes exhibition. It was winner-take-all with the winner getting $14,000.
Because of their powerful offense, and the fact that they had two 30 game winners (John Clarkson and Jim McCormick) and another rookie ace (Jocko Flynn--who won 23--including 14 in a row), Chicago was the clear favorite. They were probably spending their money before the series even began.
In true Cubs fashion, they choked when it counted. With Future Hall of Famer John Clarkson on the mound, and future Hall of Famer King Kelly behind the plate, the winning run was scored by the Browns in Game 6...when a player stole home.
The White Stockings got exactly zero dollars for their effort.
