Perry quickly began investing in land in Travis County. He has said much of the property he bought in the 1990s was spots that he had hoped his family would settle on but that his wife always said were too remote.
In 1991, Perry found 29.1 acres of raw land near Lake Travis for sale via a Federal Deposit Insurance Corp. liquidation auction. He purchased the lot for $55,288 with plans to build a home there but soon put it back on the market. Three years later, he sold the property for $125,000, according to tax records.
Perry bought 10 acres of undeveloped land in 1993. That property drew interest from Michael Dell, a computer magnate who needed Perry's tract to connect his new home to municipal sewer lines. Dell took the property off Perry's hands for $465,000, more than triple what Perry had paid for it two years earlier. Perry reported a $342,994 profit on the sale in his 1995 tax return.
Texas Democrats have repeatedly questioned the sale over the years, in part because Mike Toomey -- an influential lobbyist and later Perry's chief of staff -- closed the deal for Perry while Perry was out of town. Perry has always said that when the bought the land he didn't know it would be so valuable to Dell.
The next year, Perry reported a $38,000 profit from selling stock in Kinetic Concepts, a medical-bed and supply company founded by James Leininger, a longtime generous donor to Perry..
Since 1996, Perry has put most of his investments into a blind trust. A spokesman for Perry's campaign could not provide the trust's current value. Though the arrangement has shielded most of Perry's investments from public view, his finances again drew sharp attention in 2007 when he reported income of over $1 million.
Most of Perry's gains that year came from the sale of a lot in the resort community of Horseshoe Bay.
Perry bought the land from state Sen. Troy Fraser, R-Horseshoe Bay, in 2001 for $314,770. Six years later, Perry sold it for $1.1 million. Perry has attributed the gain to a favorable market for Hill Country land.
"We bought a piece of property, the property appreciated and we sold it," Perry said last year.
Critics including the liberal watchdog group Texans for Public Justice have suggested a dubious deal, considering that the man Fraser bought the land from and the man Perry sold the land to were business partners.
"I think there's a narrative developing around Rick Perry that kind of encompasses the Texas political culture in that we're a pay-to-play state," said Craig McDonald, director of Texans for Public Justice.
The Perrys have yet to file their 2010 taxes and have requested an extension, according to a representative. In 2009, Perry reported $135,278 in income as governor. From 2004 to 2009, Anita Perry reported average annual pay of $63,111 from work with the Texas Association Against Sexual Assault.
Perry's financial history will provide a contrast to that of some rivals on the national stage. While primary rival Mitt Romney made a fortune in the private sector before jumping into politics, Perry's biggest gains have taken place while he has been in elected office.
Unlike President Barack Obama, who has made millions of dollars from two books, Perry directed proceeds from one of his books to legal defense for the Boy Scouts of America and proceeds from the other to an Austin-based conservative think tank.
This report includes material from the Star-Telegram archives.