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Everyman Ed Lee

December 11, 2013, 5:18 PM UTC

Andy Serwer took a break from his day job as managing editor of Fortune to profile San Francisco mayor Ed Lee for Bowdoin Magazine, the alumni publication of both Serwer and Lee’s alma mater, Bowdoin College. (Serwer is class of 1981, Lee class of 1974). The following is the entirety of the story from Bowdoin Magazine’s Fall 2013 issue.

Fortune writer (and fellow Bowdoin graduate) Beth Kowitt wrote about sibling entrepreneurs for the same issue.

Some five hundred volunteers at a help-the-homeless day in San Francisco line the bleachers of the Bill Graham Civic Auditorium. They’re listening to the mayor of their city, Edwin Mah Lee give a speech, and they’re absolutely rapt — which is a bit surprising because Lee’s remarks seem to be perfunctory. In a speaking style about as fiery as Bob Newhart’s, the mayor talks about the need for compassion and equality, and also about jobs and growth. Pretty standard stuff.

And neither does Ed Lee cut a particularly impressive figure. He’s around five feet, five inches with medium length silvery hair, and sports a non-descript suit. He has a bit of a paunch from eating too much of homemade casseroles like his “No-longer secret Poongaloong.” (See recipe here.) His trademark mustache is restrained. As for his glasses, well maybe they were stylish when he was back at Bowdoin. Maybe. And yet, reflected in his eyes are five hundred faces hanging on every word.

Why is that?

To answer that question you have to understand how contemporary American history and a remarkable personal story brought this man and this city together.

First consider the strikingly eclectic group of volunteers gathered in the auditorium (named after the late legendary rock concert impresario). Here sit aged radical activists — decades removed from their SDS/Black Panther/Yippie glory days — some who don’t look that different from the folks they’re trying to help. Also present (and of course there’s all kinds of overlap here) are African Americans, Latinos, and Asians — including Chinese, Koreans, Japanese, and Samoans. Then there are doughy corporate types from sponsoring organizations such as Blue Cross and Sprint. And finally there’s a strong showing of ‘shiny happy people,’ aka young techies from companies like Twitter, Facebook, and Square, whose most pressing issues are (in order of importance) working like maniacs, conducting multi-million real estate transactions, and consuming mind-bending cabernets. Now imagine processing all this history and humanity and then calmly and extemporaneously drawing the crowd together and inspiring them.

That Ed Lee can so readily connect with these people has everything to do with his most unusual life path: The son of poor working class Chinese immigrants from Seattle who spoke Cantonese, he graduated from Bowdoin and then Cal Berkeley’s Boalt Hall law school to become San Francisco’s first Chinese-American mayor.

But Lee’s appeal also has everything to do with the authenticity and content of his character. While many fellow California politicians trade on their larger than life personas — think Arnold, Nancy Pelosi, and Jerry Brown — Lee stands out for not standing out. Example: The first word out of Ron Conway’s mouth to describe Ed Lee is “humble.” To Conway, one of the most prominent venture capitalists in the Bay Area, Lee’s demeanor is a refreshing contrast to the brash tech CEOs he spends his days with. Lee also has a deceptively high EQ, (emotional quotient), meaning he is extremely adept at reading and understanding others. But even more than that, Lee has a deep and sincere intellect honed by a range of experience, not the least of which was his time at Bowdoin, where he sought out and soaked up the totality of what the college had to offer. Ed Lee really is a typical American success story that is of course paradoxically singular by definition.

It may be difficult for younger alumni to process that only forty years ago, Asian students were so unusual that when Ed Lee joked with his classmates that he was the brother of martial arts movie star Bruce Lee, they believed him. “I had never been East before — all I had seen was a picture of Bowdoin — and I remember that first winter. Eight feet of snow,” Lee says to me. I’m sitting with the Mayor in his office across from his desk, and behind him I can see pictures of his family, President Obama, Golden State Warriors’ Stephen Curry and (readers will be happy to know) a ceramic polar bear.

“We had to dig ourselves out of the dormitory [Appleton], and I went, ‘What the heck is this?’ And I got one of those long green coats from an Army surplus store, really warm with the head cover in it,” he recalls with a grin. “My roommate was from Portland, Maine, and he was a violinist but very down to earth and spoke in that Maine twang. And I would be joking about how slow society was in Brunswick, Maine, and he would say: [Lee imitates Maine accent here] “Mr. Lee, you’re cruisin’ for a bruisin’.” And I said, “What!? What did you say?” — but he was very courteous, very polite.”

Ed Lee wasn’t exactly a fish out of water at Bowdoin though. An exceptional student and a leader growing up, Lee was class president of Seattle’s Franklin High School, (which was then a third Asian, a third white and a third African American). He played varsity tennis and sang in an elite choral group where he was mentored by another Chinese-American class president two years older than him, Gary Locke, who would go on to be Governor of Washington, Secretary of Commerce, and is currently U.S. ambassador to China. Lee was also the only one of his four brothers and sisters who pitched in significantly to help his father, Gok Suey Lee, with his work as cook at a restaurant. Gok, who fought in World War Two for the U.S., came from the city of Taishan in Guangdong Province (southeastern China near Hong Kong) in the late 1930s. Lee remembers working with his father: “There were a couple of incidents in the restaurant where he had to take food to Caucasian customers and he would get cursed out, being called a ‘chink cook’ and stuff for whatever reason it was. I would be in the car, help him carry some of the food into the house and he’s, ‘Go sit in the car,’ and I’d be hearing some yelling but I would be afraid to ask him what that was about.”

And then tragedy stuck. Gok Suey passed away when his son was fifteen and Lee’s mother had to double down working as a waitress and seamstress. Meanwhile Ed had college to consider. While his mentor Gary Locke went on to Yale, and his friends were looking at the Ivy League too as well as the University of Washington, a high school history teacher convinced Lee that he would do better at a smaller school. Head of Bowdoin admissions Richard Moll happened to be in Seattle, met Lee, liked what he saw, and helped Lee secure an Alfred P. Sloan scholarship, a grant from the foundation founded by the late CEO of General Motors who had built the automaker into the largest company in the world.

Lee’s time at Bowdoin was so productive that it may make you, dear reader, feel like a bit of a slacker. So brace yourself: Ed was a Dean’s List student, a James Bowdoin Scholar, a Surdna Foundation Fellow. He was on the Student Council and the National Model United Nations Club, and he was president of the U.N. Club. He was in Bowdoin’s Upward Bound program. He lettered in tennis, was co-captain and a co-recipient of the Samuel A. Ladd Tennis Trophy his senior year. He graduated summa cum laude, was elected to Phi Beta Kappa, and was awarded a Thomas J. Watson Fellowship. He studied Russian and Mandarin, the latter then taught by the college bursar, a woman from Taiwan. (A quick Russian anecdote: One summer Lee dropped in on a rural Russian Orthodox church — probably in Richmond, Maine. Lee was all wild-haired and sunburned dark from working outdoors. “I started speaking Russian and they thought I had dropped in from Mongolia,” he laughs.)

Lee was also active in fervent campus politics of the time. “Ed arrived at Bowdoin with the rest of our class in the fall of 1970 following great on-campus political turmoil that spring due to the Communist coup in Cambodia,” says classmate Jed Lyons. “I remember he was a terrific guy, always smiling, congenial, warm, and with a heat-seeking sarcastic sense of humor. We laughed about our single-sex predicament, cadged free beers at the frat parties, and had a wonderful four years at Bowdoin. Ed was a very popular but quiet member of the class.” Says Professor David Vail, who helped Lee with his Watson application, “[Ed]…was a very engaging person and a smart, insightful student: mature beyond his years. My most vivid memories are of a road trip to Boston for a Union for Radical Political Economy weekend conference with elements of an early-70s teach-in and a ‘be-in.’”

Taking his high school counselor’s advice, Lee spent time conversing with a range of professors including Rensenbrink, Donovan, Morgan, Potholm, and Langlois. This intellectual environment prompts some unlikely similes from Lee: “Bowdoin to me was like a monastery. [Remember the college was all-male at the time.] You could explore anything you wanted as long as you were serious about what they were trying to teach you. And absorb it, and then allow it to blend in you. It was like that famous television series Kung-Fu. David Carradine was in the monastery, and they were trying to give him discipline, so when he goes out into the real he would remember that discipline as he experienced all these things. I look at Bowdoin as being kind of like giving you that intellectual ability to appreciate how to learn.”

Lee’s Watson Fellowship took him to Hong Kong and into China (which was very difficult to enter at the time), where he was to study the Chinese Youth League and compare it to the Boy Scouts. After that he was keen on a career in the U.S. Foreign Service. But his plans went awry. In China, he discovered that the Youth League, Chairman Mao, and the Cultural Revolution weren’t any new sort of political paradigm after all, and in Hong Kong, junior diplomats warned him that his long hair and politics might make the Foreign Service a bad fit. Meanwhile he met his future wife Anita. So what to do? He simply followed the same impulse that hundreds of Bowdoin students have: “I said, why don’t I just do a little bit of insurance and apply to law school?” Lee was accepted to Cal on scholarship, and off he and Anita went to Berkeley. But Lee had been to the Bay Area one time before. In fact he was drawn back in part by what he describes as a powerful life experience that originated at Bowdoin.

In the spring of 1972, some McGovern for President organizers arrived on campus through Professor Rensenbrink looking for students to work on their campaign. Lee’s name came up, and the McGovernites recruited him to work in San Francisco’s Chinatown organizing citizens for McGovern and against Hubert Humphrey. “I said ‘San Francisco?’” recalls Lee. “[But] I accepted. It tested me for the first time, organizing, as a sophomore at Bowdoin.” Both the work and locale appealed to Lee greatly.

And so not surprisingly, as Lee worked his way through law school, he became active in organizing the Chinese community in San Francisco, helping to improve living conditions in public housing and with civil rights issues like diversity in the city’s fire department. By the time he graduated from Berkeley in 1978, Lee was already deep into the swirling stew of San Francisco politics, beginning work as a managing attorney for the San Francisco Asian Law Caucus. Eleven years later Lee switched sides to work for change within the system — as they used to say — when then Mayor Agnos named him the city’s first Whistleblower Ordinance investigator. Over the next two decades, Lee would hold a variety of city positions, ultimately reaching city administrator, where in early January of 2011, the board of supervisors voted for Lee to be interim mayor, succeeding Gavin Newsom, who had been elected lieutenant governor of California.

There was just one problem. Lee had pledged not to seek election if appointed, and now that he was in office, 1) he found that he was an effective leader and enjoyed the position and 2) a coalition of supporters had started a “Run Ed Run” campaign encouraging him to run. Lee told the San Francisco Chronicle at the time: “I know it might be hard for people to understand that change — but my change of mind in seeking this office has everything to do with wanting what’s best for this city.” His mind made up, Lee garnered support from the tech community in particular. “I didn’t know Ed Lee from a hole in the wall then,” says Ron Conway, “but I got to know him as I saw him work to help tech companies create jobs in the city by creating tax-free zones for Twitter and other companies. That sold me.” Conway helped produce an “Ed Lee, 2 Legit 2 Quit” video featuring MC Hammer (the tune being a remake of Hammer’s 1990’s classic “2 Legit To Quit”), Brian Wilson, (the edgy San Francisco Giants pitcher), former Mayor Willie Brown, football great Ronnie Lott, Twitter co-founder Biz Stone, and Yahoo CEO Marissa Mayer, among others. The surprisingly hip video became a bit of a YouTube sensation and helped propel the Mayor to victory in November of 2011.

Even for someone with Lee’s political touch, San Francisco is devilishly difficult to govern with its congestion, traffic, and super-dense population (number two in the nation after New York City), plus items like an earthquake-damaged mega-bridge, and the aforementioned heterogeneous populace. While the city’s operating budget is now in decent shape thanks to an improving economy, San Francisco still has $4.4 billion in unfunded liabilities the city is projected to owe for retirees’ and employees’ health care obligations. And, some say Lee is too close to tech companies like Twitter and Lee counters that you can’t attract and retain companies like that without engaging them, and that one of the most important metrics of progress is job creation. And in fact over the past few years, the city has become a real rival to Silicon Valley for hot tech start-ups. “He really understands what it takes to help companies like ours succeed,” says Jack Dorsey, co-founder of Twitter and CEO of mobile payment start-up Square, during a visit by Mayor Lee to Square’s new headquarters on Market Street. “But it’s not just about business with him. He’s a deep thinker who cares about people,” says Dorsey.

“Marc Benioff, [billionaire founder and CEO of] asked me the other day, ‘what is that you want to accomplish?’” Lee tells me as we walk back from Square to City Hall. “He was talking about my education agenda, but it reminded me about Bowdoin. And I remember professors Rensenbrink and Donovan asking me that kind of thing, and how much I thought about it and how important those kinds of questions are.” I ask Lee if he ever imagined being the mayor of San Francisco when he was younger. “Oh no,” he laughs, but he acknowledges he had thought about being a community organizer, which he did do, and connecting people that way.

Consider the connecting in Ed Lee’s own story: A young Chinese-American student from Seattle is given a scholarship endowed by the CEO of a Detroit auto giant to attend a small college in Maine where he reads Hawthorne and Longfellow and is then recruited by operatives of a presidential candidate from South Dakota to organize a community in San Francisco which inspires him to a life of public service in a city where he eventually becomes the mayor. A singular American success story if there ever was one.

Mayor Ed Lee’s life, with its unlikely twists of fate, has been all about understanding what connects us and then applying what he learned to make new connections himself. And now you can begin to understand why the faces of all those volunteers are reflected in his eyes.