Matt Mahan’s Journey to Mayorship

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An outsider runs against the political establishment

By Chris Corona

On a surface level, Matt Mahan’s image coincides with trappings of wealth and influence. He went to elite schools like San Jose’s Bellarmine College Preparatory and Harvard University and has ties to technology industry luminaries like Mark Zuckerberg and Sean Parker, as well as the support of San Jose Mayor Sam Liccardo. His political adversaries have tried to frame him as a “Republican” out of step with progressive San Jose.

His origins, however, don’t suggest a silver spoon upbringing or conservative roots, though that hasn’t stopped competing interests from running against him as if he were a fourth-generation member of the Bush family. Even though he’s declared himself a pro-choice Democrat, mailers by the labor-aligned independent PACs suggested he might not be a reliable ally on reproductive rights.

Mahan called the political hit a “distraction” to draw attention away from the political establishment’s failed policies on homelessness and public safety. Calling attention to those failures have cast him as an outsider running against the establishment and have likely cost him endorsements from officeholders, including his council colleagues, who have thrown their wholesale support behind the candidate most closely aligned with the valley’s political leadership.

Mahan’s campaign released a poll this week showing that while opponent Cindy Chavez enjoys much higher name recognition and a 1 point lead amongst likely voters, 25 percent of the electorate is still undecided and shares Mahan’s view that San Jose is not headed in the right direction.

He’s always been a bit of an outsider. The mayoral candidate grew up in the Santa Cruz County agricultural town Watsonville in the 1980s and ’90s. Although his family owned the house in which they lived, they could be described as working class—as were most of their neighbors in the mostly Latinx community of 52,000. His mother taught at a Catholic school in Salinas, and his father was a union letter carrier. 

“I remember waking up at the crack of dawn, and farm workers were already out there working,” Mahan says. “That always left an impression on me.”

Because both parents worked, his mother would drop Mahan off at school early. Mahan recalls that one of the teachers, Mr. Washington, would let Mahan and his sisters into his classroom before school started. After school, he took his sisters to the public library to do homework until they could be picked up. 

“Even though we didn’t have much money, my parents were incredible in being proactive and getting us into different activities that weren’t too expensive. One time, they even got […] my sister and I enrolled in an after-school art program. That stuff makes a big impact on you when you’re a kid. You remember those things, and they build confidence and interpersonal skills.”

Beyond art, Mahan had a love of sports. In his childhood and teenage years, Mahan played basketball, soccer and wrestling. He carried his passion for soccer into his later years as a soccer coach at Joseph George Middle School while working as a teacher for the nonprofit Teach for America.

“That was a weird thing. For a kinda shy kid as I was growing up, through sports and great mentors, teachers, family friends, playing team sports and individual sports like wrestling all helped build confidence and my interpersonal skills.”

“What I love about Watsonville is that it has that small-town feel where everybody knows everybody and it has incredible access to nature. Where we lived on the outskirts of the town, we had access to a creek on the hillside and I spent much of my childhood outside. I have a great love for nature.”

Despite the beauty of the surrounding area, life in Watsonville had its challenges.

“It is a small town, with a strong sense of community, primarily agriculture—people work hard. It has that small-town culture. On the other hand, it struggled quite a bit. We had a high unemployment rate, high crime rate, a lot of gang activity and a lot of violence. It ended up being that two people in my neighborhood were drug dealers.”

Mahan stops to reaffirm his fondness for Watsonville. His mom still lives there, and he regularly visits; as a teenager, however, he felt some growing pains.

“When you turn 13 or 14, you start to wonder about your place in the world, and it … felt kinda restraining at the time. I don’t mean anything negative. … It is just the nature of a small agricultural town.”


His parents always striving for the best for their children’s education, Mahan was encouraged by his family to take the entrance exam to Bellarmine College Prep, an all-boys Jesuit school. Bellarmine since its inception in 1851 has provided students with the highest academic support resulting in 98% of students moving onto a four-year university and an average ACT score of 31. Mayors Tom McEnery and Sam Liccardo are Bellarmine alumni and have endorsed Mahan for the city’s top position.

“I will never forget, my dad took me over and we got lost in East San Jose and barely made it in time for the test. I was late and everyone had already gotten started. I remember walking in and sitting down. They were all San Jose residents and knew each other. I was one kid from Watsonville that came in late to take the test.”

After a grueling examination, Mahan was accepted into Bellarmine but faced the realization that the entrance exam was just the first test. The next hurdle was figuring out how his family could afford the private-school tuition. Luckily the answer came in the form of a 200-hour work-study scholarship.

“They gave me this great deal. If I came during the summers and worked with the maintenance crew, they would pay my tuition,” said Mahan. “Then the rest of the year, I was just any other student there to get an education, and I did. Bellarmine is a very special place with a great sense of community and tradition.”

During the summers before each school year, Mahan worked with the maintenance crew watering plants, landscaping and joking with the permanent crew members, who welcomed him warmly.

“When I showed up on day one, the only people I knew were the grounds crew.”

Now able to attend Bellarmine without worrying about tuition, he still faced a four-hour round trip bus ride on Highway 17 each day of the school week.

“My dad would get me up in the dark at 4:45 in the morning and I would be so tired he would pick me up off the bed and put me on the cold floor just to wake me up.”

Early mornings and long bus rides resulted in an early appreciation for caffeine. Despite being a self-described awkward kid and, for all purposes, an outsider, Mahan found himself not only welcomed at Bellarmine but also able to attain a leadership position. It is easy to imagine seeing Mahan as the student body president at Bellarmine as a small preview of his later political career. A sentiment shared with Katie O’Keefe, a close friend to Mahan and his family, who took early notice of his leadership skills.

“You kind of think ‘big fish, small pond,’ but every time he moved ponds, he is the big fish,” said O’Keefe when describing how Mahan adapted after stepping into Bellarmine.

O’Keefe first met Mahan while she attended Presentation High School, an all-girls Catholic school in San Jose. She met Mahan along with the man who would become her future husband at a school mixer. Mahan and the O’Keefe family are still close friends. Her first impressions of Mahan were in stark contrast to how Mahan thought of himself.

“Matt has always been impressive. When you met him, you knew he was going to do great things.”

This stands in contrast to Mahan’s self-described shyness—especially when O’Keefe describes student body president Mahan’s responsibilities.

“Since it was an all-boys school, it didn’t have cheerleaders, so they had yell leaders. So at football games he would be out there riling up the crowd, wearing these rugby polo shirts, and if the team scored they [Mahan and other yell leaders] had to do push ups.”

Being student body president was not always shaking hands and being a pep leader. Sometimes it was talking about uncomfortable topics or standing up for others.

“Being in an all-boys Catholic high school at that time, talking about homophobia wasn’t the most comfortable thing, but it was important to me. Two of my best friends there were not fully accepted by many of my classmates,” said Mahan.

Mahan used his platform to disclaim bigotry through speeches in front of classmates and faculty, and in a column for the school newspaper.

“That was where I became interested in social justice. I ended up getting involved in student government. I pushed the campus to move away from sweatshop labor for its apparel.”


Mahan, who valued academic achievement, knew just which university he wanted to attend.

“Every day when I would wake up on the cold floor, looking up at the ceiling, I had a picture of Georgetown on the ceiling, because that was my dream for years was to get into a great university. Because I wanted greater opportunities. I didn’t want to live paycheck to paycheck like my parents did.”

While his eyes were on Georgetown, O’Keefe recalls, that is not where he ended up.

“He really wanted to go to Georgetown,” O’Keefe says, “but he reached for the stars and got into Harvard. He was in shock and awe when he got in.”

Mahan traveled to the East Coast with a friend visiting with his family. He took the time to visit both Georgetown and Harvard before arriving at his final decision. 

“I kinda fell in love with Cambridge and Harvard because it is a place driven by ideas and people interested in thinking about what’s right, should be, and what the future is like. Sorry, I guess you can call me a big old nerd.”

“I saw a lot of my core views challenged in a really productive way,” said Mahan. “I kinda see myself as a centrist or a moderate who tries to take what is most true of the progressive and conservative traditions in our country—because Harvard and my interactions with fellow students and professors made me realize that no ideology has a monopoly on the truth.”

Harvard at this time turned out to be a powder keg of innovation mixed with opportunity. Mahan succeeded in his economics program and became student body president once again. While later graduating magna cum laude (and also meeting his future wife), he also rubbed some influential elbows. 

Mahan arrived at Harvard precisely at the same time as Mark Zuckerberg. 

“He and Mark [Zuckerberg] lived in the same dorm,” said O’Keefe. “I think for some of the reasons he got into tech later was because he was offered the opportunity to help with the original Facebook. He turned it down because he wanted to do the class president thing. He was constantly volunteering, working on political campaigns, and then it [Facebook] took off. 

A 2005 article in the Harvard Crimson noted Mahan’s disillusionment with Harvard’s career track system. “They’ll, you know, live in a beautiful suburb where they never have to confront homelessness and poverty, and all end up in the same retirement home where they’ll play golf until they die,” he was quoted as saying about his classmates.

The article also noted his volunteer work with Democratic nominee John Kerry’s 2004 presidential campaign and his activism with the campus’ Black Men’s Forum president to create a fund to protest Harvard’s investment in a Chinese state energy corporation linked to Sudanese genocide.

Two years later he volunteered for two weeks as an early supporter of Sen. Barack Obama’s nascent presidential campaign. “I was in Iowa in 2007 before the caucuses and spent two weeks knocking on doors and getting people out in the snow. … It was freezing cold. I’ll never forget how cold it was.”

Mahan also became a public school teacher at Joseph George Middle School on San Jose’s East Side, and a “card carrying member” of the teacher‘s union. “He didn’t regret [not joining Facebook] because he had that North Star, more just like it was a once-in-a-lifetime opportunity for our generation to be part of something like that. So when the apps started being created for Facebook, it was originally Causes he worked for.”

Co-founded by Sean Parker and Joe Green, Causes created a social platform for users to share fundraisers and raise awareness for nonprofits. The app aligned with what O’Keefe describes as Mahan’s “North Star” of social justice. Mahan eventually became the company’s COO and then its CEO. The experiences Mahan picked up at Causes allowed him to extend his business ventures with his old dorm mates into Brigade, a successor social advocacy platform that was later sold to Pinterest.

This incursion into tech eventually did come to an end and Mahan turned his eyes back to his ultimate goal: becoming mayor of San Jose. Mahan’s political career is still very fresh, having first been elected only two years ago, a small time in comparison to his opponent Cindy Chavez, who has been a dominant figure on the local political scene since the 1990s.

“I always thought it would be the best job in the world. I am more into action and getting things done. You get to champion initiatives and push the bureaucracy to deliver results. I like the idea of trying to organize people around solving problems,” says Mahan.

“The city [San Jose] has given me incredible opportunities. I just fell in love with it when I came here. Maybe it is a little bit of nostalgia from my youth, but I came here in the ’90s and it just felt like a city on the rise.”

Only time and the voters will tell if he will reach that North Star.

“Matt has always wanted to be mayor of San Jose. It wasn’t a stepping stone; it was specifically for San Jose,” says O’Keefe. “I think growing up in Watsonville, San Jose was the big city, and he wanted to be part of it.”

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