“I lived at 5012½ Del Monte Avenue from 1994 to 1996. It was exactly one block from the cliffs, where I could sit on a bench, smoke a cigar, drink a beer, and watch the sun set, and two blocks from Newport Avenue — so I had it made. It was a little studio apartment. I paid $390 a month, all utilities included. People say, ‘You can’t afford San Diego; it’s too expensive.’ It’s not too expensive. I was living right by the beach. I spent all my weekends out on the pier in the sun, getting the New York Times, hangin’ out all day, drinking coffee, smoking cigars.
“In 1997, I moved out of O.B. when I went down to Mexico to become an ‘international social entrepreneur.’ It was actually a housesitting gig. At an art-gallery reception, I met this woman, Jane, who was building a house in Todos Santos; she already had a place in Cabo she was renting, properties in Northern California, and her own place in Bird Rock. She took me down there for a week, and I fell in love with the place. Todos Santos — town of 4000 — it’s near the Tropic of Cancer, about 50 kilometers north of Cabo. Not too hot, except for a couple of months in the summer, when some of the Caribbean humidity seeps up. But with the Pacific breeze, it’s like paradise.”
It was a life of poverty, and he loved it.
“I found 12 different jobs. I knew everybody. I learned how to swear in Mexican Spanish. I was doing marketing translation, tutoring Americans’ kids for 30 pesos an hour. Jane’s husband needed a gardener. He paid me eight pesos an hour. He was a cheap gabacho; sometimes I was paid in food. When I was a gardener, I had enough money to buy my caguama of Tecate, a little more than a quart, some limes, cucumbers, and two or three bolillos — delicious Mexican bread.
“I had the greatest time of my life, the greatest adventure for the least money. I’m very resilient, a cultural chameleon. I had the sunshine, the music, and the food, a rotation of three meals: rice and beans, tortillas, and pasta. I was in a rental house overlooking the Pacific, which roared like a freight train all night; out the front door was a 6000-foot mountain range and desert all around. But I didn’t know where the next peso was going to come from; I thought I might have to live on mangoes, which grew all over the place. Jane says that I was a ‘private Peace Corps’ — working with these great Mexicans down in Latin America, making a difference, helping these micro-enterprises grow. This was my dream, the peak — the colmo, as they say in Spanish, of my career. The experience. I was rich, a Bohemian living on his wits. It wasn’t the Harvard MBA training; it was just me, seeing if I could survive.
“After that, I lived in a chili shed with two other guys and their wives — we called it a ‘company store’ because it had a loom there where they made the blankets. Chili sheds are three-sided buildings open in front. We had a cold running tap across the way on a vacant property but no bathroom. That was okay, except I picked up Giardia and I got irritable bowel syndrome, which I still have.
“I was deported in April 1999 for selling Indian blankets on the roadside of the main highway. You don’t think they have immigration laws? There were 10,000 gabachos down there. The Mexican government started to crack down. The officers were nice guys. They let me go back to pick up my things and withdraw my savings, a couple of hundred dollars. I bought everybody some tacos, and I said, ‘I’m thirsty’ — so we stopped and I bought a six-pack. I asked the guy riding shotgun if he wanted a beer, and he took one. I asked the driver, and he took one, too.” At San Ysidro, the U.S. Customs guy laughed. ‘You were deported?’”
In June 2000, Buddy made his way back to New England — and homelessness. “I slept one night in the airport, but they kicked me out. I spent two nights in a park, Post Office Square in Boston, then a homeless shelter from late June 2001 to July 2002. I finally got Section 8 housing in Chelsea.”
During the early 2000s, Buddy — only a few miles from where Harvard had conferred his MBA — worked four hours a day in a shelter kitchen, warming up food and setting out plastic. Eventually, after dumbing down his résumé by omitting his master’s degree, he landed positions in small social-services organizations, helping street people find work. In January 2009, Buddy had “a certain falling out” with his boss. He asked her: “‘If you were to terminate me, would I be eligible for unemployment?’ ‘Of course,’ she said. It was a win-win. I got $400-a-week unemployment for 99 weeks. With the Great Recession and Obama, I picked the perfect time to become unemployed.”
Buddy also thought it would be the perfect time to snag a Peace Corps post.
“I started on the application. First, I had to pay $200 to have a goddamned Spanish oral-proficiency test that lasted all of 15 minutes. I aced it — got 8/10, which means I’m just below a native speaker. I had a great rapport with my interviewer, Jennifer. My business-development background was impeccable. I had it locked up. You can’t pick any countries out — they tell you where you’re going — but I knew it was Latin America, and that was enough to me, although I would’ve preferred Mexico.
“I spent $2000, half my savings, for dental work they demanded. The government isn’t going to pay for you to go overseas, even as a volunteer making a minimal stipend, if you’re gonna have your teeth falling out when you’re over there. They also said the medical board was gonna check me out, look at my records, so I had to be honest about the irritable bowel syndrome. They don’t want to risk people getting sick out in the field. I happened to pick the worst possible condition, the easiest one to rule me out. I kept insisting to them that I’d never missed work in ten years, was never late because of it — managed it — but they didn’t care. I went through three levels of appeals, but they wouldn’t give. I was devastated. Medically Disqualified.”