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."

What Happened to 'Ray'

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."

Watching Obama's Presidential Campaign Behind Bars

During the fall and winter, Kakugawa, 47, watched the presidential campaign of his friend explode from his prison cell, where he was serving six months for a parole violation.

"We saw it and I was like 'Oh my God,'" Kakugawa recalls. "I got a letter from my ex-wife saying 'Well he's done it now, what are you going to do?' And then I got a letter about two weeks before I left saying, 'Everyone's looking for you, call him collect right now.'"

Obama has been reluctant to talk publicly about the hard times that have fallen upon his friend. "That's a shame," he told the Chicago Tribune when informed that Ray was then in prison. "Suddenly, everybody who's ever touched my life is subject to a colonoscopy on the front page of the newspaper."

Calling the Senator

Shortly after getting out of prison earlier this month, Kakugawa walked into a pay phone at the intersection of 66th and Figueroa, right off the 110 highway near Watts in Los Angeles. He was patched through to Obama's executive assistant, whom Kakugawa told, "This is Keith Kakugawa otherwise known as Ray in the book," he says. "She said 'Oh my God,' and she, put me right in touch with him" on his cell phone.

"He just left the Senate floor," Kakugawa says, growing emotional. "He asked about my dad -- I told him I was proud of him."

Obama told Kakugawa he had to go -- he was heading for a campaign event -- and put him in touch with an assistant, Devorah Adler, who helps the senator keep track of friends and family. Kakugawa says Adler told him, "Senator Obama would like to help you, what can we help you with immediately?"

And he said his response was simple: "Money."

"I'm homeless," Kakugawa explains. "I sleep in a car. I ask everyone for money."

Conflicting Stories

But Obama campaign officials says Kakugawa's comments were not as he is now portraying them. They say he threatened to tell negative stories about the senator to the media if money was not wired to him.

Kakugawa denies this. He says he still thinks of Obama as "a little brother. That's why this hurts so much that his campaign headquarters said I would extort or doing anything to hurt this man's campaign." He says he understands why Obama would distance himself from him. "I'm a convicted felon," he says. "The Republican party, the Clinton campaign would tear that up."

A Window Into the Senator's Life Story

Whatever happened, Kakugawa provides an interesting window into the senator's biography, which he has presented as one of his central selling points.

"He is such a people person now, it's really amazing because he was a very, very shy -- I wouldn't say introverted -- but he was just a very shy, cautious kid," Kakugawa says. "I didn't see him as a politician, I saw him as maybe a lawyer, as a doctor, as even a kids' counselor or a coach."

Obama wrote of losing himself in drugs after Kakugawa graduated from Punahou in 1977. "Pot had helped, and booze; maybe a little blow when you could afford it," Obama wrote. But Kakugawa says he never saw any of that.

"Barry and I drank," he says. "Well, I drank and forced Barry to drink, let's get that clear. 'C'mon Barry you're drinking, you're drinking.' You'd see Barry have one beer after I'd have seven." Kakugawa speculates that Obama may have tried drugs after he left since he no longer had a close friend with whom he could talk candidly.

"He did have a lot of race issues, inter-race issues, being both black and white, you understand?" Kakugawa, who himself is half black and half Japanese. "He never really realized his full potential until he went to college."

He recalls fondly introducing his friend to the "black parties" on the island. "They found out who he was and he was the center of attraction," he says. "'Cause he was the new meat on the hoof, especially by the girls."

Falling on Hard Times

Since Kakugawa talked with ABC News, he's fallen on even harder times. Though the California Department of Corrections denies it, he has heard there's a warrant out for his arrest because of the extortion claims by the Obama campaign. His friend Jason's car broke down on the Interstate 10 highway. And he regrets how everything has gone down with his friend.

"He doesn't know realistically that if he just talked to me, took the time to just sit down -- I would just like to say 'Hey look, your campaign's great, but you need to do more or show more,'" Kakugawa says. "Whether I'd be that person who shows the world, 'Hey, he does really care about people that have had this and that,' that's what I would like have conveyed. Barry really does care about people. The people around him don't -- Win or lose, Barry will be able to get in contact with me."