The Underdog Lover’s Guide To The World Series

Don’t know much about baseball but want a team to root for? We’ve got you covered

The 1908 Chicago Cubs. (Image via Chicago History Museum)

The Chicago Cubs and the Cleveland Indians face off in the 2016 World Series, which began Tuesday in Cleveland with an Indians win in Game 1. The Cubs haven’t been to a World Series since the early days of the Truman Administration and haven’t won it all in something like 637 years. The Indians, meanwhile, appeared in the series as recently as 1997, but haven’t won since the ’40s.

Barring some sort of divine intervention, tear in the space-time continuum, or total obliteration of our planet due to a power failure in the computer lab of the alien running the humanity simulation—all of which seem almost as likely as one of these teams actually winning a World Series—at least one extended sports drought will end and one long-suffering fan base will rejoice.

Really, both teams present varying degrees of feel-good, underdog stories. It’s easy to root for either, but for non-baseball fans, perhaps hard to choose.

We’re here to help.

There is plenty of between-the-lines analysis of this best-of-7 series, so let’s look at some other key factors to consider when picking a winner:


Chicago: Cubs

Cleveland: Indians

Edge: Tie. It’s hard not to adore a cute little bear, and it’s equally as challenging to feel all that great about the “Indian” nickname, but in an honest fight between the two, the cubbie might be in trouble.


Chicago: Steve Bartman—and, you know, an actual goat

Cleveland: Art Modell and LeBron James

Edge: Chicago. (C’mon, it’s a goat!)

The infamous goat. (Image via Twitter)


Chicago: See aforementioned goat

Cleveland: The Curse of Rocky Colavito

Edge: Chicago. The goat curse is among the GOAT curses. And while the Colavito curse is baseball specific, Cleveland also suffered from the “Cleveland Curse,” pertaining to Cleveland sports as a whole. Then came LeBron James. Well, he came, then he left. But he came back.

Wrigley Field. (Image via Wikimedia Commons)


Chicago: Wrigley Field

Cleveland: Progressive Field

Edge: Chicago. The former “Jake by the Lake” in Cleveland is great, but it ain’t Wrigley. And being named after chewing gum is cooler than taking your name from an insurance company. Plus, Wrigley’s got ivy!

Image via Flickr


Chicago: Deep-dish pizza, sausages, Italian beef, Cracker Jack, Chicago-style hot dog

Cleveland: Polish Boy sandwich, pierogies, chili, ribs, pork chops

Edge: New York. Better pizza. Though finding a surprise in your Cracker Jacks is far preferable to finding one in any of these other food options.


Chicago: Millennium Park, the Art Institute of Chicago, Wrigley Field, The Field Museum, Navy Pier, Willis Tower, Adler Planetarium

Cleveland: Rock and Roll Hall of Fame, Cleveland Museum of Art, West Side Market, Progressive Field, Lake View Cemetery, USS Cod Submarine Memorial, Cleveland Botanical Garden

Edge: Tie (largely thanks to the wise words of Alan Freed)

Joe Walsh. (Image via Wikimedia Commons)


Chicago: Kanye West, Smashing Pumpkins, Chicago, Sam Cooke, Jennifer Hudson, Muddy Waters, Earth, Wind & Fire, Wilco

Cleveland: The Pretenders, Nine Inch Nails, Joe Walsh, The O’Jays, Dean Martin, The James Gang, Tracy Chapman, Jim Brickman

Edge: Cleveland. Chicago loses points for Kanye, and Joe Walsh is just that cool. Plus, rock and roll!


Chicago: Oprah, Harrison Ford, Hillary Clinton, Michelle Obama, Robin Williams, Mr. T, Ernest Hemingway, Al Capone

Cleveland: Paul Newman, Bob Hope, Halle Berry, Dean Martin, Tom Hanks, Toni Morrison, James Garfield

Edge: Oprah. Even if she’s an import from Mississippi, among other places. She was Chicago’s best acquisition since Fergie Jenkins in 1966—though Cleveland should get credit for importing Howard the Duck. Actually, no it shouldn’t.


Chicago: The Windy City, My Kind of Town, Chi-Town, Second City

Cleveland: The Mistake on the Lake, The Rock and Roll Capital of the World, Sixth City, Forest City

Edge: Chicago – unless one counts “Mistake on the Lake” as a positive moniker.


Chicago: Henry Rowengartner, Saturday Night Live’s Bill Swerski Super fans

Cleveland: Ricky “Wild Thing” Vaughn, Harry Doyle

Edge: Cleveland. #winning


Chicago: 29

Cleveland: 13

Edge: Michael Jordan


Chicago: Lake Michigan

Cleveland: Lake Erie

Edge: Cleveland. Erie has a cooler name, and Chicago isn’t even in Michigan!

So there you have it. Chicago has more going for it in its World Series matchup with Cleveland—which, of course, gives the Indians even more “under” status in the battle of underdogs. So if you want to buck (a greater amount of) history and back the team with more intangibles, don your Cubs gear. But if you want to stick with the long shot, support Planet Cleveland.

And if you want a good slice of cheese, go to Manhattan.

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