Keith Kakugawa: President Obama's best friend from high school 'brutally beat and raped woman in her apartment' Old friend: Keith Kakugawa has been arrested and charged with a slew of felonies including sexual assault and battery President Obama's high school best friend, who at one time was 'like a brother' to him, has been accused of brutally raping and beating a woman, it emerged today. Keith Kiyoshi Kakugawa, 54, from Eureka, California, was arrested at his home last Sunday and booked into Humboldt County Jail on suspicion of false imprisonment, sexual penetration by force, oral copulation by force and battery. The arrest is the latest in a long list of convictions for Kakugawa, who was close friends with the President when they both attended Panahou High School. Since then, their lives have gone down completely different paths and Kakugawa is said to be so bitter over it, he even threatened to reveal stories from their school days after Obama became president. 'It's a sad tale of how two young boys who were best friends in high school took drastically different paths in their lives,' Kakugawa's father Kenneth told the National Enquirer. 'When Keith started to face hard times, he grew resentful and bitter of Barry's success. 'I'm sure [the President] would be disappointed to find out he has been arrested for rape. They were as close as brothers at one time in their lives. The 54-year-old has been in and out of prison, mainly for possession and dealing of cocaine, and spent some time living on the streets due to alcohol and drug problems. Arcata Police Department Sgt Keith Altizer said detectives spent most of September 13 collecting evidence from the victim after she was attacked. Kakugawa was arrested later that day. The victim told police she went to dinner with him and when they went back to her apartment he punched, slapped, sexually assaulted her and held her against her will. Back in the day: President Barack Obama, left, and Keith Kakugawa, right, are seen in their high school yearbook pictures when they were 'like brothers' at Panahou school Obama wrote in his autobiography of Kakugawa: 'We'd fallen into an easy friendship, due in no small part to the fact that together we made up almost half of Punahou High School's, pictured, black population Kakugawa is being held on $400,000 bond and if convicted, faces a lengthy prison sentence. A source close to the former Wall Street trader told the Enquirer this may lead him to reveal his stories about the President. 'Keith knows a lot of secrets that could prove to be embarrassing for the commander-in-chief if they get out,' he said. 'They are mostly youthful indiscretions, but he would know more about Obama's teenage drug-taking than anyone. And now that he's really desperate and facing a lengthy prison stretch, he could spill the beans.' Consequences: Kakugawa is being held on $400,000 bond and if convicted, faces a lengthy prison sentence, which some people worry will lead him to blab his stories about the President Kakugawa's father said: 'It's a sad tale of how two young boys who were best friends in high school took drastically different paths in their lives' Obama wrote about his former best friend in his autobiography Dreams From My Father: A Story of Race and Inheritance, but referred to him as 'Ray' to protect his identity. '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,' the President wrote. I enjoyed his company. He had a warmth and brash humor. Kenneth Kakugawa said his son got in touch with Obama in 2007 during his first White House campaign but claims Obama brushed him off and passed him along to his assistant.