Heir to a railway and property fortune, Yoshiaki Tsutsumi's rollercoaster ride has sunk to new lows lately.

If ever a billionaire could be called a poor man, Yoshiaki Tsutsumi is the man.

In December 2006 the 71-year-old Japanese tycoon, six times named by Forbes as the world’s richest man, received a rare dose of good news.

Tsutsumi owns the Seibu Lions, a for-profit baseball team in the top Pacific League. The Lions were on shaky financial ground and their stadium in the Greater Tokyo area badly needed sprucing up. But Tsutsumi was unwilling or unable to come up with the money.

Enter the Boston Red Sox, which swooped in and bought the Lions’ star pitcher Daisuke Matsuzaka for a record US$51.1 million. Suddenly the Lions were back in the swing, with funds to do up their home stadium and enough to spare to buy a few more promising stars who will hopefully pick up the slack left by Matsuzaka's departure.

This is a sad come down for Tsutsumi, now reduced to selling his best sports asset to raise money. Tsutsumi, a hard driving man, inherited the Seibu Railway, a rail and property group, from his father, Yasujiro Tsutsumi, arguably Japan’s most famous post-war rail baron. (His half brother Seiji, from the first wife, was given a fledging retail business when their father died in 1964. Seiji built it into the giant Seibu Saison chain. The two brothers are on bad terms.)

Japan went through a boom in the 1980s. At its height, the grounds of the Imperial Palace in Tokyo were said to be worth more than the entire state of California. Seibu Railway then owned about one-sixth of all land in Japan. Yoshiaki Tsutsumi's wealth was valued at untold billions.

Then the Japanese economy crashed and the highly indebted Seibu Railway crashed with it. Tsutsumi saw his wealth shrink. He branched into sports marketing, setting up the Seibu Lions and building a stadium to lure the baseball-crazy Japanese youths. Tsutsumi also pushed into other sporting areas and was instrumental in Nagano’s successful bid for the 1998 Winter Olympics.

But in 2004, Japanese officials raided the headquarters of Seibu Railway. Talk was that Tsutsumi had seriously offended someone at the highest levels, perhaps even then Prime Minister Junichiro Koizumi, so much so that his political connections were not enough to shield him from a thorough investigation.

Documents in the Seibu HQ confirmed tips that Tsutsumi had been under-reporting the shareholding ratio of major shareholders including himself. In March 2005 he was fined five million yen (US$42,000) and received a 30-month jail sentence, suspended for four years. Seibu Railway was delisted from the Tokyo Stock Exchange.

Tsutsumi went into damage control mode and tried to restructure his company, not without intervention from his half brothers—Seiji, now 78; and Yuji, now 64. Eventually Seibu Railway's parent company Kokudo was reformatted into Seibu Holdings, with Tsutsumi’s stake reduced from 36% to just 5%. Cerberus, the aggressive American fund, is now the largest shareholder.

It is anyone's guess how much Tsutsumi is worth today. In 2005 it was said he still retained enough assets to be worth US$3 billion. Last year he appeared on Forbes’ billionaire list at US$1.2 billion, barely scraping past the minimum qualifying conditions. He could soon disappear from the list altogether.