Even before buying Lanai, the sixth-largest of the Hawaiian Islands, Larry Ellison was spending money like few other CEOs in America. In the mid-2000s Ellison, the founder of the computer behemoth Oracle [ORCL Loading… () ], commissioned what was then the biggest yacht in the world, the 452-foot Rising Sun, at a reported cost of $270 million dollars. (He later sold it and has since bought another, smaller yacht at around 250-feet). He’s owned multiple planes, including a Gulfstream that served as the design inspiration for Steve Jobs’s plane. An avid tennis fan, he bought the Indian Wells tennis tournament for a reported $100 million in 2009. He reportedly spent $100 million or more on his America’s Cup sailing race win in 2010. Robert Frank CNBC Reporter & Editor His biggest spending, however, is real estate. Noone knows exactly how many properties Ellison owns, but publicly available records show that at one time, he owned the following: Malibu, CA – Five adjacent lots on Carbon Beach. San Francisco – A 10,742-foot home in Pacific Heights, which was at the center a tree dispute. Woodside, CA – Two properties, including a 23- acre property modeled on a Japanese emperor’s palace. Newort, RI – A mansion formerly owned by the Astor family Koyto, Japan – An historic garden property Rancho Mirage, CA – The 240-acre Porcupine Creek estate, which has its own 19-hole golf course. It’s no wonder The Wall Street Journal dubbed Ellison “one of the nation’s most voracious consumers of trophy real-estate.” Why does he buy so much real-estate? Brokers and real-estate experts who have worked with Ellison tell me that Ellison focuses on one-of- a-kind, super-luxury properties in prime locations. He views them as long-term investments rather than temporary trades or places to live. (He has rarely, if ever, stayed at the Rancho Mirage location, for instance.) “He looks for properties that are truly rare and special,” said one broker who had worked with Ellison. Sometimes he pays full price but he is also a value hunter. The Rancho Mirage property, for instance, had once been on the market for more than $75 million. Ellison bought it for $42.9 million. There is no question that Ellison has enough wealth for all of his personal pursuits. Bloomberg ranks him as the sixth richest man in the world, worth $36.4 billion. Still, there is a difference between liquid wealth and paper wealth. Oracle doesn’t comment on Ellison’s personal life or spending, but it’s known that the vast majority of Ellison’s wealth is tied up in his company’s stock. In the past, his need for cash has strained his balance sheet. In 2002, Ellison’s financial advisor pleaded with Ellison to cut down his spending because he was reaching his credit limit of more than $1 billion. “I’m worried, Larry …” the accountant wrote in one email found in court documents. “We have a freight train going down a track, hitting a debt wall.” Of course, back then, Ellison was only worth around $19 billion.