Not your Average Candidate

The bike ride from Winthrop House to Cambridge City Councilor Leland Cheung’s house-turned-campaign headquarters takes me illegally up Mill Street, ...

The bike ride from Winthrop House to Cambridge City Councilor Leland Cheung’s house-turned-campaign headquarters takes me past the Common and the Quad, past the fire station at Sherman Street and its sign reminding Cantabridgians to vote, November 8th. It’s a 15-minute ride, tops, but by the time I reach Cheung's house, I have trouble recognizing that the neighborhood is only a mile from Harvard Square

I don’t see anywhere to lock my bike, so I throw the lock through the spokes of the front tire and park it in the driveway. Right at 9:30 a.m., I knock on the basement door, as instructed. I am greeted by G. Anthony Morse, Cheung’s campaign manager.

Morse offers me a seat and asks if I have any questions. He tells me “Leland” will be right down. The councillor is always referred to by his first name. Councillor Cheung is the name of a stale elected official; Leland is just a 33-year-old newlywed, hoping for your vote.

When Cheung walks down the stairs, he greets me, quickly shakes my hand, and sits behind his desk. He turns to his computer, where he notices that there is a ribbon-cutting at Cambridge Rindge and Latin School (CRLS). It starts in 20 minutes.

Cheung asks, “Should I wear like, khakis and a dress shirt or should I wear—” “Yeah,” Morse interrupts. “I’d say it’s Saturday, it’s a little more casual.” Cheung exits the room and returns, a few minutes later, in a navy suit. He occasionally poses these types of questions and listens to the answers, but in the end he relies primarily on his own judgment.

And he’s out the door. We plan to meet later on the campaign trail—I’ll go canvassing with Cheung’s staff, then he will catch up with us.

We wait for the other members of the staff. Cheung’s aide, Megan E. Montgomery, arrives first, Dunkin’ Donuts iced coffee in hand, with Press Secretary Christopher R. Kellogg close behind. We pile into Morse’s SUV and drive back down Garden Street towards Cambridgeport, where they’ll be canvassing. Cambridgeport is downstream of Harvard, closer to MIT than to the Square. The staff members are all fairly recent college graduates, and talk quickly turns to cars, families, significant others.

The fact that Leland Cheung is a smart man can hardly be called into doubt. Later in the day, upon seeing his framed diplomas, one atop the other on the wall, I ask, “So, is that a double major?” “It’s two different degrees,” he informs me. A Bachelor of Arts in economics and a Bachelor of Science in physics. Both awarded by Stanford University. Not too shabby, but possibly overshadowed by his current educational endeavor—a dual degree MBA/MPA at the MIT Sloan School of Management and the Harvard Kennedy School.

And Cheung puts that intelligence to work. When the Cheung campaign claims that no one canvasses the way they do, it’s easy to believe. The strategy is, I was informed, a trade secret, and my one caveat for the day was to keep it that way. All I will say on the subject is that it is highly effective.

Eventually, Cheung arrives in Cambridgeport. He parks his car, gets out, and talks quickly with his staff. Tablet in hand, he sets off to knock on doors. I follow him.

Cheung, unlike many politicians, is in this business to get things right. He’s the kind of man who’s interested in optimization, who worked to make his canvassing system as efficient as possible. He explains his decision to pursue two undergraduate degrees at once, saying, “It’s kinda like, you’re paying for it, you might as well maximize what you’re getting out of it.”

For Cheung, facing his first re-election since taking office two years ago, politics is about fixing problems, not about putting on an act for a camera. When a photographer asks him to position himself closer to his constituents to better frame a photo, he balks at the idea. When he utilizes lines, as all politicians do, he delivers them with a tinge of discomfort. “Historically,” he repeats over and over, “the newest member of the council is the one that’s not reelected, so I definitely need all the number one votes I can get.”

There are nine at-large Cambridge City Councillors who each represent the entire city. When voters go out to the polls, they rank each candidate, starting at number one and going down as far as they wish. As a candidate, the higher you’re ranked the better, and the number one vote is the crown jewel of each ballot.

Once we finish up in Cambridgeport, I climb into the passenger seat of Cheung’s two-door car and we drive to his fourth appearance of the day, the CitySprouts Festival at a Cambridge elementary school. City Council and School Committee candidates are out in full-force. Cheung works the crowd—seeks out people he knows, talks to a few he doesn’t. He jokes with Jamie Towns, who has been married for 15 years, about his recent honeymoon to Shanghai. “It was more like a shopping excursion for her. I wanted to go to a beach and relax, she wanted to go shopping,” Cheung confides. “She won.”

This is our last event, so we take our leave and walk back to the car. I see a parking ticket in the back seat. I ask if he’s allowed to just waive them. He laughs. “I got one this morning. I ran into the CRLS thing, I’m like, alright, it’s supposed to be done in an hour. And the meters are only for an hour, so I just put an hour in the meter and then of course it starts late and goes long, and I’m up on stage, so it’s not like I can just get up and leave. Just like, ‘Excuse me, I’m going to go feed my meter.’ So then you get a ticket. And because you’re a City Councillor, you can’t even complain about them.”

We arrive back at 157 Garden Street, where the day began, and he sits down at his desk. I look around and after a few minutes, I leave him to his homework.