"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."
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."
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."
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."