T-pisode 71: T Does New York City in 3 Paragraphs

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Shady street vendors were my favorite

*I’ve decided to do a series of blog posts that capture my travels throughout my life. In 3 paragraphs. I’ll post them every once in a while. Some places I’ve been to a few times, others only once. And some I will probably never go back to because of what went down there.

This is the big one! This Boston guy does New York City. What is my take on NYC? It’s one big contradiction really. From how it started for me to how I feel about the city today and everything in between. I started going down to NYC when I was 16 years old. My cousin and I spent many Summer weekends there getting into shit during our mid to late teen years. Even with the Boston/NY rivalry between the cities’ teams and people, we really enjoyed going to this version of NYC. The New York City I’m talking about was old school, more dirty than it is now, before Giuliani cleaned it up, before Snoop came through and crushed the buildings, before Gotti went in the can, when Pac & Biggie were beefing and you could get anything new and/or bootlegged on any street corner New York City! We went down to NYC for fun, money-making schemes and a shit load of trouble. And by trouble, let’s just say one of those 7 famous incidents where I should’ve died took place in NYC. In the back of a shady restaurant. Over some stupid shit. Fun. But very stupid.

The first time my cousin and I got off the Greyhound bus we immediately went looking for bootleg Rolex watches and bombarded a businessman holding a briefcase standing at the corner. We slapped the briefcase asking “Watchu got in there man?!” He thought we were trying to rob him because he ran. Guess he worked on Wall St. and wasn’t a street vendor. Our bad. I blame movies and rap music for my first impressions of NYC. I used to go down there and treat the city like it was my own personal playground. At that time you could walk into a liquor store and buy 40s and drink them in Times Square out of paper bags at the ages of 14 & 16 while ordering food in a McDonald’s. I know this because that’s what my cousin and I did. Boy did people stare. Another time we also managed to eat and drink for free by putting our tab on some couple’s bill at the All-Star Café. That place was like Planet Hollywood but with athletes. We Beantown hustled that one. Another time we stayed at the Millennium and had “hot” calling card numbers to which we used to call everybody back home in Boston. Our other buddies came down the next day and we robbed the hotel’s liquor cabinets and drank booze and ate fancy cheeses all the way back home on the bus to Boston. I don’t know why honestly.

While there are many more experiences that were also insane during those dirty teenage NYC years, things changed the older I got. Those trips were replaced with business trips and sports trips once I graduated college and entered corporate America. NYC itself changed. In my eyes, it became very corporate, gimmicky and overrated. Boston’s teams and the city of Boston itself came up and the rivalry grew. I hated this “new” New York. That is, up until this past January. I went down to NYC to see a good friend. One of my “Bullpen” girls. She took me around the city to some fun spots. With some of her great friends. During a Jets/Colts playoffs weekend mind you! And you know what? I had a great time. Yep. I did. Not ashamed to admit it. Maybe it was her. Maybe it was the cool people I met. Maybe it was the good food and lots of booze. Maybe it was me getting older and not holding onto grudges. I don’t know. All I do know is, this Boston guy has to admit that he kind of likes New York City. But I love Boston the best.

Until next time. Always take it there.



  1. New York’s one of my favorite cities. I wish I would have gotten there before 9/11. My guess is it’s changed.


    1. 9/11 definitely changed New York but it was already changing in a lot of other ways before that. Boston’s better. 😉


  2. My best friend from colglee and I are both moving to Boston on the 1st. She is a Yankees fan and I am a die-hard Red Sox fan. This series couldn’t be any more perfectly timed.-Ace


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