Recently, The Westword got to speak with Westhill alumni Jake Sherman, who is currently a senior writer for POLITICO and a former managing editor for the Westword. He spoke to us about his Westhill experience, journalism, and even his favorite food when he comes back to Stamford.
The Westword (TW): How would you describe your experience at Westhill?
Jake Sherman (JS): My experience at Westhill was, overall, very good. I went to a small Jewish school for kindergarten through eighth grade, so I was very interested in trying something new. I met a whole new set of people at Westhill.
TW: What was your position on Westword and were you involved in any other clubs?
JS: I was the managing editor for the Westword. I tried to become Editor-In-Chief but Dana Schuster, a friend of mine to this day, decided that I was not the best candidate. It was a crushing disappointment but I cared a lot about journalism and Westword. So I stayed on.
HAPPY BDAY to @DanaSchusterNYC of the NY Post. She blocked me from becoming editor of my high school paper, but i survived! (I’m not bitter)
— Jake Sherman (@JakeSherman) May 19, 2017
TW: What was your favorite/least favorite thing about Westhill?
JS: Favorite thing: The Westword. Least favorite thing: the early start time.
TW: Favorite Teacher?
JS: Saul Dicker was my favorite teacher. He passed away a few years ago.
TW: Where did you attend college and why did you choose it?
JS: I went to George Washington. I was interested in politics and journalism and I figured that being in Washington was a pretty good place to be.
TW: What is your current job at Politico and what is a typical day like?
JS: I write Politico’s Playbook, which is the flagship morning newsletter for Politico. I’m up very early — between 3:30 and 4 — and I write the newsletter with my longtime collaborator, Anna Palmer. I’m also working on a book about Congress. That takes up a good bit of my time. I also appear frequently on television.
TW: What is the most unique opportunity you’ve been able to experience throughout your career in journalism?
JS: I’ve gotten to know many members of Congress, attend four political conventions, eight States of the Union. I’ve traveled the country and the world writing about politics.
TW: Do you have any advice for aspiring journalists?
JS: If you want to be a journalist, write and read a lot. It sounds simple. But seeing and understanding how great writers structure their thoughts is very helpful.
TW: Favorite Food?
JS: Sorrentos salad. Also my go-to spot in Stamford.
TW: Favorite professional sports team?
JS: I’m a big Washington Nationals and George Washington basketball fan.
TW: On your Twitter bio, it says you love Grateful Dead & Phish…. If you could only listen to one for the rest of your life who would it be and why?
JS: I can’t choose between the Grateful Dead and Phish. They are both great, and they complement each other.
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