Q&A with Jake Sherman, POLITICO writer and Westhill alumni

Jake Sherman attended Westhill and now works as a writer for Politico // Photo courtesy of Politico.

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.

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.

To follow Jake Sherman on Twitter, click here.

To follow The Westword on Twitter, click here.

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