Richard A. Smith's House

Smith's father gave him a head start on his bank account by founding a small chain of theaters in the 1920s that would become General Cinema. Smith used to play tennis with Bob Kraft and is the uncle of Philadelphia Eagles owner Jeffrey Lurie.

Now in his eighties, he built — and has been selling off — an empire that included a soda bottler, a major publishing company, and department stores. In 1989, Smith sold his independent soda-bottling company to PepsiCo for $1.88 billion, then the highest price ever paid for a bottler. He used some of the proceeds to buy Harcourt Brace Jovanovich for $1.5 billion. Then Harcourt sold in 2001 for nearly four times that. Finally, he and his family grossed more than $600 million in the $5.1 billion sale of Neiman Marcus.

In 2006 he was ranked the 32nd wealthiest Bostonian at $500 million.