Meet the 2nd Busiest Person on the Upper West Side: Gale Brewer’s Scheduler

By Gus Saltonstall

New York City Councilmember Gale Brewer’s calendar has long inspired feelings of astonishment and reverence.

As penned in a City & State article from 2018, “Gale Brewer’s peers in politics are in awe of her public schedule.”

Councilmember Keith Powers told the publication at the time, “I would be dead if I had Gale Brewer’s schedule every single day.”

When West Side Rag spoke to Brewer, who represents the Upper West Side, on Tuesday, she mentioned that she had been to five events the evening prior, all after 6 p.m.

“I don’t understand why people don’t go to events,” Brewer said in a phone call. “It’s hard. Most of them are between the hours of 6 and 8 p.m., and it’s very difficult to get to all of them but I do try. You develop relationships in the community you wouldn’t by staying at home or at the office.”

While Brewer is the person who makes it to all of the events, whether it be a community board gathering, a gala, or a school board meeting, there is another person who plays an instrumental role in her whereabouts at any given time.

Caleb Gutwillig — her scheduler.

The Rag interviewed Gutwillig, an Upper West Side native, this week to get a better understanding of what goes into crafting Brewer’s weekly schedule.

WSR: How many events does Gale go to in a given day?

Gutwillig: It depends on the day, but on average, around eight to 10 events, but on some days it goes all the way up to 15 to 20. She’ll start in the morning with rallies or meetings with other councilmembers, maybe a press conference, then go to all of these committee hearings, to another press conference, maybe more rallies, and then after that, she’ll have four or five different galas and community meetings that she’ll want to go to in the evening.

WSR: And what time does that all start and end?

Gutwillig: Generally, around 8:30 a.m. to 9:30 p.m.

WSR: And how do you actually put the schedule together?

Gutwillig: It starts with a Google Calendar. Then, every evening because Gale is old school and likes to work with paper, I type up the Google Calendar version into a Google Doc, and then email that document to Gale and all of the staff members. She then prints it out and brings it with her. So, when folks see Gale with a big packet that she is flipping through, that’s the schedule.

WSR: And you do that every week?

Gutwillig: I do that every day. Every day is a new packet. The packet changes enough each day that if you did it for the week, you’d get to Thursday and it wouldn’t make sense anymore.

WSR: So, the schedule changes day-to-day?

Gutwillig: The day comes and we’re being flexible, but yes, the schedule is constantly being set. Right now, I’m thinking about tomorrow and today, but also thinking about January 15th. When the week of January 15th comes around, though, you can’t control what’s going to happen in the community. There might be a major issue or event in the district that requires Gale’s attention and work, and then all of a sudden, what you’ve scheduled for January 15th in early December is no longer an option.

WSR: Stepping back a bit, how and why did you end up working in the councilmember’s office?

Gutwillig: I’ve been interested in local politics my whole life. My mother is a public school teacher and I remember growing up constantly hearing about who the head of the Department of Education was, and in most cases, what they could be doing better. I’m from a civic-minded family, so I’ve always been interested in community politics. Recently, I left a job in the federal government for this more value-based work in local government.

(Gutwillig started in his role as scheduling director in March of 2025, and Brewer had high praise for his work since.

“I don’t know anybody like him,” she said. “What kind of adjectives can I use that are superlative? I don’t have just one. It’s [scheduler’s job] more important perhaps than any other job in the office and I’ve never met anyone who has done it as well. He gets everything done between 10 and 6. He’s 100 percent correct, not 99 percent, and he does it effortlessly. I don’t even have to think about the day-to-day. I just do what he says.”)

WSR: What are your other responsibilities in the office?

Gutwillig: A lot of constituent services. I try to help with that as much as I can. My colleagues, Rosalba and Elise, when the issue is very difficult, it goes to them, but if I am able to refer people to different services based on my own knowledge, then I step up as much as I can. I also help to oversee our very robust intern program. I try to look out for events that interns would be interested in and [that would be] valuable for them.

WSR: Were you aware of the scope of Gale’s public schedule before you took the job?

Gutwillig: Yes. But actually seeing the quantity of invitations and requests for meetings has given me a newfound appreciation. I always say, I’m exhausted putting together her schedule, so I can only imagine how exhausting it is to actually live that schedule.

WSR: Why does Gale find it so important to go to so many events in a given day or week?

Gutwillig: For her, it’s not about getting credit for going to events. She goes to all of these different events because it allows her to put faces to names, and then to put faces to the issues that people have and [she] gets a better understanding of the issues different community groups are having, different organizations. It allows her to get a hands-on, firsthand look at district issues.

I can’t tell you how many times that she goes to an event on Wednesday and then on Friday I’m getting an email for a meeting request about a very detailed issue. It seems to me that they’re having very substantial interactions that lead to followup meetings, which lead to inter-agency meetings, that lead to letters being written, and going to an event kickstarts that process.

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