Barack Obama transferred from Occidental College to Columbia University in 1981, his junior year. Although he left Los Angeles with enough ambitious propulsion to carry him into a more active period, he instead receded into the most existentialist stretch of his life. As he put it himself dec­ades later during an interview in the Oval Office, “I was leading a very ascetic existence, way too serious for my own good.” In most outward ways, compared with what had come before, his life in New York was a minimalist one, without the sprawling cast of characters that had surrounded him at Oxy and in Hawaii and Indonesia. He felt no attachment to Columbia or to the first jobs he landed after graduation. But it would be a misreading to say that he was tamping down his ambitions during that period. Just the opposite, in fact. If anything, his sense of destiny deepened. He was conducting an intense debate with himself over his past, pres­ent, and future, an internal struggle that he shared with only a few close friends, including his girlfriends, Alex McNear and Genevieve Cook, who kept a lasting rec­ord, one in letters, the other in her journal.

“Where Am I Going?”

It is exponentially easier to look back at a life than to live it forward. In retrospect it becomes apparent that New York was crucial to Obama. If he had not quite found his place yet, he was learning in which directions not to go and how to avoid turns that would lead him off the path and into traps from which it would be hard to escape. Even when he was uncertain about much else, Obama seemed hyper-alert to avoiding a future he did not want.

At age 20, Obama was a man of the world. He had never been to south-central Kansas or western Kenya, the homelands of his ancestors, yet his divided heritage from Africa and the American heartland had defined him from the beginning. He could not be of one place, rooted and provincial. From his years living in Indonesia, where he was fully immersed in Javanese schools and culture; from his adolescence in Hawaii, where he was in the polyglot sea of hapa and haole, Asians and islanders; from his mother’s long-term commitment to development work overseas; from his friendship with Pakistani students at Occidental and his extended visit to their country—from all of these he had experienced far more global diversity than the average college junior. He knew the ways of different cultures better than he knew himself.

Obama’s first apartment in New York, which he shared with Phil Boerner, a friend from Oxy, was at 142 West 109th Street. Heat and hot water were scarce commodities. When the nights turned colder, the roommates took to sleeping bags for warmth and spent as little waking time in the apartment as possible, holing up in Butler Library, at 114th, parts of which were open all night. Some mornings, eager to flee their quarters, they walked to the corner of Broadway and 112th to eat at Tom’s Restaurant, the place immortalized later as the fictional Monk’s, a familiar meeting place for the characters on Seinfeld. A full breakfast went for $1.99.

The loneliness of Obama’s New York existence emerged in his letters to Alex McNear, a young woman from Occidental who had enchanted Obama when she was co-editing the literary magazine Feast, and with whom he reconnected when she spent the summer of 1982 in New York. Alex had always been fond of Barry, as she called him, and “thought he was interesting in a very particular way. He really worked his way through an idea or question, turned it over, looked at it from all sides, and then he came to a precise and elegant conclusion.” When Alex came to New York, she gave Obama a call. They met at an Italian restaurant on Lexington Avenue, and, as she remembered the night, “we sat and talked and ate and drank wine. Or at least I drank wine. I think he drank something stronger. It was one of those dark, old Italian restaurants that don’t exist in New York anymore. It was the kind of place where they leave you alone. I remember thinking how happy I felt just talking to him, that I could talk to him for hours. We walked slowly back to my apartment, on 90th, and said good-bye. After that we started spending much more time together.”