Over the course of three days, bike messenger Zesty Meyers is hit by a car, barely avoids being killed by a host of gangsters and is on the run from police. Despite his ordeal, Zesty helps solve one of Boston’s biggest heists. This is Boston’s underworld in the ‘80s and ‘90s. Adam Abramowitz sets his cinematic, adrenaline-pumping story in the city’s pre-gentrification and Big Dig days for his first book, “Bosstown.” Abramowitz recently spoke to JewishBoston about his Boston Jewish roots, his writing process and Zesty as his alter ego. 

How deep are your Jewish roots in Boston?

I went to Solomon Schechter Day School in Newton after a three-year stay in Israel with my family. We lived in Jerusalem from 1969-1972, where my father was involved in organizing one of Israel’s welfare agencies. Hebrew was my first language, and when we returned to Brookline, I was 6 and refused to speak English. I still know a decent amount of Hebrew, and when I recently went back to Israel, I was amazed at how much came back to me.

Boston is also a character in your book. How did you come to know the city so intimately?

After I graduated from Brookline High School, I worked as an assistant bar manager at Legal Sea Foods in Chestnut Hill. My entry to the South End [of Boston] was through a woman I dated from the restaurant. I lived in the lofts in the South End for almost 15 years, just like Zesty did. In fact, I gave him my actual address in the book—42 Thayer St. But names [in the book] have been changed to protect the guilty.

How did you integrate your fascination with Boston’s underworld into the novel?

Devlin McKenna is very much based on Whitey Bulger. In many ways, the book is a love letter to Boston, in that I wrote it like a letter to a lover who once loved you, abused you, tolerated you and eventually cut you loose. Even though that lover chewed you up and spit you out, you can’t get over them. Similarly, you have to have a toughness to live in Boston. The city forced me to mature. I worked a variety of jobs that included being a bike messenger like Zesty.

The book is so much in Zesty’s head. Is there a part of you in him?  

Adam_Credit Antonia Abramowitz
Adam Abramowitz (Photo: Antonia Abramowitz)

I am very much like Zesty. Some of it is a point of pride and some of it I have to apologize to people for. In many ways I was very fast and slippery, but managed to stay out of trouble. I also ran a poker game at a moving company where I worked. I participated in backroom poker games too. I was never connected directly to Whitey Bulger, but I used to bet on sports through a bookie who was associated with him. Like Bulger, my character McKenna stayed underground for so long. That fascinated me. How can someone in today’s world disappear for so long? Bulger must have planned so far in advance to do that.

What were some of your other regular poker games?

After I moved to New York City [from Boston], Sarah Silverman told me about a game with other standup comedians that took place every Monday night. We’d play poker until five in the morning and then go out for breakfast as the city started to wake up. Poker has always been a skilled game. You have to believe in a karmic flow and in getting lucky once in a while. You need that luck to get by. Sometimes it comes and sometimes it doesn’t. What I loved about poker and playing with these comics was that I lied to them without animosity. It was expected. There are no grudges in poker. 

Zesty and his family are Jewish. Was that a natural choice for you, and how does it serve your story?

Zesty’s mother, who disappeared when he was very young, is Jewish. His father is also Jewish. Jewish identity is not played up so much in this book, but I have a two- book deal from St. Martin’s Press, and it’s much more prominent in the next book. As Zesty’s father’s Alzheimer’s becomes worse in the second book, Zesty needs to prepare for his father’s departure. The Alzheimer’s is also a vehicle for me to explore memory, which has always fascinated me. We think we remember things the way they were, but sometimes we want to think about our memories only in ways that we can process them. 

How did you structure this intricate plot?

I mostly wrote this book while I was asleep. My writing process was to get up in the morning and write until I had to nap. I always had a pad and pencil next to my bed because so many plot points came to me in my sleep. There was a lot of napping and coffee involved in the writing of this book.

What’s in store for Zesty?

Zesty will have his own book series and he will take on a different role. Being a bike messenger is a very physical job. It has a limited shelf life. Either the street claims you or something happens to your body. Consequently, Zesty will become more of an investigator and he will learn certain things about Bosstown along the way. I’ll also continue to incorporate the music scene in Boston into the story. Boston was once a hotbed of local music, and Zesty has that eternal soundtrack in his head after he has the accident on his bike. I owe a debt of gratitude to these bands for inspiring me and empowering me creatively to share with other people. 

Adam Abramowitz will read from “Bosstown” at Brookline Booksmith on Wednesday, Aug. 9, at 7 p.m.

This interview has been condensed and edited.