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Last Time the Cubs Won the World Series refers to a series of jokes about Major League Baseball's Chicago Cubs who, before November 2nd, 2016, had not won a World Series championship since 1908. The jokes spiked on Twitter during Game 7 of the 2016 World Series between the Cubs and Cleveland Indians as users mocked attempts by Fox Sports Network and others to provide historical context for how long it had been since the Cubs won the World Series by stating facts about 1908.
The Cubs' World Series championship drought, the longest in baseball history, has long inspired jokes about the Cubs' 20th century misfortune, including self-deprecating ones from Cubs fans. One of the best known early references to the Cubs struggles came from Cubs announcer Jack Brickhouse, who called Cubs games on WGN-TV from 1948-1981, when he noted "Anyone can have a bad century" in 1977.
The advent of the internet brought jokes about the Cubs' long futility to the web. The earliest memes came in the form of demotivational posters and image macros, and were as a way to mock Cubs fans. While it's unclear which was the first internet image to reference the Cubs' futility, a demotivational poster celebrating the 2005 World Series win of the Cubs' crosstown rivals, the Chicago White Sox (shown below, center), indicates they were being made as early as 2005.
Jokes and fascination with the Cubs' had small resurgences in 2008, the 100 year anniversary of their last World Series win, and in 2015, when the Cubs lost to the New York Mets in the National League Championship series.
2016 World Series
In 2016, the Cubs had the best record in the National League and were one of the favorites to win the World Series heading into the postseason. This lead to a spike in articles listing historical events that had yet to happen the last time the Cubs won the World Series, including pieces from Heavy.com and Business Insider. The Cubs beat the San Francisco Giants and Los Angeles Dodgers in the National League playoffs to reach the World Series, where they faced the Cleveland Indians.
On November 2nd, the Cubs faced off against the Cleveland Indians in Game 7 of the World Series. As the Cubs jumped out to an early lead, Neil Degrasse Tyson began to tweet facts about what had happened the last time the Cubs won.
This drew the mockery of Twitter users, who found the tweets a pedantic buzzkill. Tyson's tweets inspired a series of jokes in which Tweeters made up absurd facts or told irrelevant information about 1908 as a way to mock the irrelevance of Tyson's tweets.
 Through The Fence Baseball – Remembering Jack Brickhouse and the origin of his “Hey-Hey!” catchphrase
 Business Insider – The world has changed a lot since the Cubs last won the World Series