Craig McCaw was a pioneer in the cellphone business, as chairman of the telecom company Clearwire. He created an empire by convincing winners of a lottery to own cellular rights to sell those rights to him in the 1980s. By the time most Americans were using the technology, McCaw controlled a significant amount of the infrastructure necessary for it to work. He and his brothers sold McCaw Cellular to AT&T in 1994 for $11.5B.
McCaw purchased his own private island, James Island off the coast of British Columbia, for $19M in 1994. He put the 780-acre private island up for sale for $78M in 2012, but no transaction was reported and it is no longer listed. The island has a Jack Nicklaus-designed golf course, a main residence, six guest cottages, an entertainment center, a gym, a pool, a spa, a store, an airstrip and a marina.
In 2012, McCaw paid the highest price ever at the time for a car: $35M for a custom-built 1962 Ferrari 250 GTO. — Scott Klocksin