Life of Obama's Childhood Friend Takes Drastically Different Path

March 30, 2007 — -- In his best-selling autobiography, "Dreams From My Father: A Story of Race and Inheritance," presidential hopeful Sen. Barack Obama, D-Ill., writes movingly about his high school best friend, whom he calls "Ray." In his first year at Hawaii's elite Punahou School, then-9th-grader "Barry" Obama was befriended by Ray, who was two years older.

"Despite the difference in age, we'd fallen into an easy friendship, due in no small part to the fact that together we made up almost half of Punahou's black high school population," Obama wrote. "I enjoyed his company; he had a warmth and brash humor. …"

With Ray, who like Obama is multiracial, the future junior senator from Illinois would discuss his complicated issues about race and the father who had left his family. The son of a white mother from Kansas and an absent black father from Kenya would experience his first real social experiences as an African-American.

"Through Ray I would find out about the black parties that were happening at the university or out on the Army bases," Obama wrote, "counting on him to ease my passage through unfamiliar terrain. In return, I gave him a sounding board for his frustrations."

But the story of their friendship is ultimately a tragic one about the promise and pitfalls of being black in America. As first reported by the Wall Street Journal, Ray's real name is Keith Kakugawa. And Kakugawa's life could not have veered more starkly from that of his old friend, the presidential candidate.

Kakugawa is currently homeless in Los Angeles, sleeping in the beat-up Mazda of his friend Jason Myles. He has been in and out of prison for the past few decades, mostly on charges related to cocaine possession and dealing.

"To be honest with you, to survive, I've moved" drugs, Kakugawa says.

His relationship with Obama was like that of brothers, Kakugawa told ABC News one recent afternoon in Los Angeles. "Everybody said they always saw him smiling and happy. I didn't. I got to see the turmoil, I got to see how he really felt. Here's a kid who was growing up as an adolescent in a tough situation. He felt abandoned, he felt that his father abandoned him and his mother was always pursuing her career."