New York vs. Chicago: The Great Debate

The recent interleague baseball match-up between my hometown New York Yankees and the Chicago Cubs gave me an excuse to make my first trip to Chicago this past weekend.

As I took in a pair of games at historic Wrigley Field, I started to learn why the Cubs haven’t won a series since 1908. Losing has become part of their appeal and their fans have embraced the concept of the “Loveable Losers.” I even saw some kid being interviewed on ESPN saying he’d rather be a Cubs fan than a Yankees fan because “it would be boring to always win.” I’ve been a Yankees fan my whole life. Trust me kid. There is nothing boring about winning.

Cubs fans and their relationship with Wrigley Field is like being in a bad relationship with a beautiful woman. They are blinded by its exterior beauty and can’t see the flaws on the inside.

On the exterior, everything about Wrigley Field looks amazing. The field has a quaint atmosphere of a minor-league park with its ivory-covered brick walls and auxiliary scoreboard. But what you’ll find in the interior are cramped seats, no video board and a trough in a disgusting men’s room where 50 men are pissing simultaneously. Oh yeah…and the team playing inside stinks.

But Cubs fans are blinded by Wrigley Field, just like a man would be blinded by dating a beautiful woman who brings nothing else to the table.

Every game is like a party for Cubs fans, where the outcome isn’t as important as having fun. Remember the crap your parents told you after losing a game in Little League, that it’s not important if you won or lost, as long as you had fun? It seems like Cubs fans live by that notion. The result is a side note to getting drunk and tossing beach balls around. I can see why Wrigley Field is called “The Friendly Confines”: Because the park is too small and their fans are wimps (except for the teenage girl that called my 63-year old father a “faggot Yankees fan”). Obnoxious Yankees fans were scattered all over that park, talking shit at every opportunity and most Cubs fans just sat there and took it. Even when the Cubs won on Friday, they failed to seize a rare opportunity to talk trash. Maybe that’s the difference between New Yorkers and Chicagoans. Perhaps they are just too polite to say anything.

As the team with 27 World Series Championships took two-out-of three from a team who hasn’t won a title in over 100 years, it became clear which city had the better baseball team. But when it comes to other important aspects, Chicago holds its own against New York City. Though I was only there a few days, I took in a good amount of the city and have drawn some key comparisons between Chicago and New York.

Cleanliness and Attractiveness
I did a lot of exploring through downtown Chicago on two hot days and it was nice to walk through a city without having the smell of rotting garbage penetrate my nostrils. The city is beautiful and cleaner than Manhattan and the skyline is just as breathtaking as the New York City skyline, if not more. Millenium Park is a gorgeous spot as well.
Advantage: Chicago

People in Chicago are WAY friendlier than people in New York. Most people in New York are miserable assholes. Just about everyone I dealt with in Chicago greeted me with a smile and usually started a friendly conversation.
Advantage: Chicago

In New York City, there is pretty much a bar on every corner. In Chicago it’s a little harder to find a good bar. Though there are plenty of bars in Chicago, New York City makes the Windy City look like a dry town.
Advantage: New York City

The traffic in both cities blows.
Advantage: push

I was very impressed with the quality of women in Chicago. There were beautiful women everywhere I went. However, there wasn’t much diversity with the ladies. Chicago featured mostly regular white girls, with a handful of attractive Spanish and black chicks. New York City has beautiful woman of all races. It’s a veritable melting pot of sweet pussy. If you apply yourself in New York, you could sleep with a woman from every continent and it probably wouldn’t be all that difficult.
Advantage: Slight edge to New York City

Sorry Chicagoans. Deep dish pizza doesn’t hold a candle to New York pizza. I treated myself to some famous deep dish Pizza at Gino’s East, which supposedly is the best place to get deep dish pizza in Chicago. It was even featured on an episode of Man vs. Food.

The idea of eating pizza with a fork and knife just felt dirty to me (and Jon Stewart would agree). I did not find the pizza as good as New York pizza and at the end of dinner all I had to show for my meal was a bad case of indigestion.
Advantage: New York

Chicago is a great city and I will definitely be back. Is it better than New York? Well I’m a little biased as a native New Yorker. So I’d say probably not. What are your thoughts? Any objective opinions here?

6 comments for “New York vs. Chicago: The Great Debate

  1. Nugs
    June 22, 2011 at 6:00 pm

    I also had this debate this weekend, as I have clients in from Chicago AND my best friend, a Chicago transplant living in LA, came to visit NYC. You’re right on all counts. I even got one of the Chicago boys to admit that our pizza is much better than Chicago deep dish (which also goes along with your “Chicagoans are nicer” theory”).

    Verdict? New York City rules, in every category. Also, LA sucks.

  2. Nugs
    June 22, 2011 at 6:02 pm

    Also, I agree. New York City girls are WAY hotter. 😉

  3. Goose9192
    October 3, 2011 at 12:11 pm

    Chicago has just as much diversity as new york does. There is hot latina, black, and asian girls here too. But because you didn’t see that part of town because you are not from chicago. On top of that because you are not from chicago you don’t know where the good bars are. Someone not from new york would say the same thing about new york because wouldn’t know where to go. Plus chicago pizza is better. Chicago is better.

  4. October 4, 2011 at 12:12 pm

    Goose, I respect your opinion but you’re wrong. It’s pretty much a fact that New York City is the most diverse place in the world. It’s just a numbers game. I’m sure there are plenty of attractive hispanic, black and asian girls in Chicago but it can’t possibly be as high as New York, simply because New York has a larger population and is more diverse.

    As far as bars, I certainly admit I don’t know Chicago very well. But I do know New York City and I can spit in the air there and my spittle will probably hit three bars.

    As far as pizza, it’s not even close.

  5. Derrick
    October 23, 2011 at 11:35 pm

    Fun article. I always thought the only people who compared New York & Chicago were people who didn’t live in either city. Either way, IMO, both of these cities are the greatest in the world. But seriously, when it comes to pizza…it’s really not close at all. Chicago owns NYC. Just saying…

  6. Gosse9192
    March 26, 2012 at 9:03 pm

    Johnny I’m sorry I took a while to reply but I also have more important things to do. It doesn’t matter if new york has a bigger population than chicago if chicago has a higher percentage of the populations of non-white people. Chicago has a higher percentage of black people than new york. That is actually a fact. I don’t know about asians or hispanics but I know that chicago has a larger percentage of blacks than new york. Again finding bars is just as easy in chicago as it is new york. Finding good ones you need knowledge of the area. Which if I went to new york I wouldn’t be able to find a good bar. And again the pizza is better. Also if you want to talk sports look at the Bulls right now compared to the knicks. Best Basketball team in the nation. Repping Chi-city baby!

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