Ed Lee, the mayor of San Francisco who died suddenly Tuesday at age 65, was an unlikely friend of the technology industry. A civil rights lawyer and housing advocate as a young adult, Lee spent his middle-aged years as a low-profile city bureaucrat. It’s as unlikely that anyone in the tech community would have known Lee as it was that he’d one day become the tech-friendly mayor of the city that is the global capital of IT.

But life takes strange twists and turns. In 2011 he was the consensus choice of the city’s bickering legislature to serve out the term of Gavin Newsom, who had resigned to become lieutenant governor. Surely the colorless city administrator would be a safe pick for preening politicians who couldn’t agree on a leader. His assurance that he wouldn’t run for a full term sealed the deal.

I first met Lee that summer, when Andy Serwer, the last managing editor of Fortune, and I visited the interim mayor in his office. Andy had a couple things in common with Lee. He had worked for years for an organization before becoming its leader. And he went to Bowdoin College in Maine, which Seattle-born Lee had won a scholarship to attend.

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Going to school in Maine was Lee’s first unlikely turn in life. He told us how strange it was for a poor son of Chinese immigrants to end up in frigid New England. Over the course of the conversation it became clear to Andy and me that Lee was going to break his pledge not to run for mayor. He did, and he won office handily later that year.

That’s when he became a friend of tech, particularly its chief San Francisco booster, Ron Conway. The tax breaks Lee offered Twitter and other companies made him a hero to tech startups and a villain to the left in San Francisco. They thought he was helping the rich, but his moves breathed life into a moribund part of town and brought numerous jobs to the city.

It was a promising start, but ultimately the huge challenges of running San Francisco overwhelmed the mayor who decidedly wasn’t a politician. He wasn’t able to get a handle on homelessness, housing costs, or congestion—all of which got increasingly worse during his tenure.

His death, from a heart attack Monday night, saddened anyone who knew what a kind and unassuming man Ed Lee was. Just three days ago the astute San Francisco Chronicle columnist Heather Knight published an account of accompanying Lee as he picked up garbage on the city’s perennially disgusting streets. She noted that he had two years left in his term and that he intended to focus his efforts on housing and homelessness. “When the end comes and that’s it, I’m going to feel OK—that I did everything I could to help the city,” Lee told Knight.

He was referring to the end of his term, not his life. San Francisco has lost a good man who did do everything he could.