A spikey-haired Takafumi Horie sat quietly as the judge read out his sentence Friday -- two and half years behind bars for violating the country's securities laws.
It was a new low for Japan's most famous dot-com mogul, a brash 34-year-old entrepreneur who transformed his Internet services firm Livedoor Co. from an unknown startup to household name -- and emerged as a nationwide celebrity.
But it is unlikely this will be the last Japan hears from the flamboyant tycoon.
Horie's glory days of dating actresses, bragging about corporate takeovers and running for parliament came crashing to an end in January 2006, when he was arrested on suspicion of illegally manipulating Livedoor's stock price.
More than a year later, Judge Toshiyuki Kosaka ruled Friday that the "prosecutors case was proven" and handed Horie what was seen as unexpectedly harsh sentence.
Prosecutors had demanded four years in prison. But in Japan, executives charged of similar wrongdoings generally get a suspended sentence and avoid jail time.
As an up-and-coming business leader, the cherubic Horie made waves as a cocky, T-shirt-clad youngster who attempted flashy buyouts of old-school mainstays, including one of the Japan's biggest media conglomerates and a professional baseball team.
A dropout from the prestigious University of Tokyo, Horie founded Livedoor in 1997. Within years, he became one of Japan's richest men and was soon a tabloid regular with a penchant for dating actresses. He nearly won a seat in parliament.
Thanks partly to this image, Livedoor became a darling of Japanese investors.
It was those investors, many swayed by Horie's charisma into playing the market for the first time, who were burned the hardest when he was arrested and the stock tanked.
Insistent on his innocence to the end, Horie would still wear T-shirts with slogans like "Billionaire Boys' Club" and claimed he was framed by a jealous old-guard elite for rocking the boat with his risky get-rich-quick maneuvers.
He is expected to appeal Friday's verdict, and is already been plotting a comeback.
In December, he said he was to build a new business for consumer space travel and is working with several people to develop a rocket in Tokyo.
But if Horie ends up behind bars, he'll have plenty of opportunity for planning. He was cooped up for three months last year before posting 300 million yen (US$2.6 million) bail, and spent a lot of time reading and doing push-ups.
Yet he insisted he lost only one thing during the ordeal.
"I lost weight," he said.