There was a time when Jody Gerut, despite his Stanford education and professional signing bonus and Major League paycheck, knew absolutely nothing about money. Oh, sure, he had a financial adviser from a reputable, recognizable firm. He was playing right in the midst of the tech bubble, and he had some stocks and bonds -- from companies like General Motors and AOL/Time Warner -- that seemed secure enough. But Gerut didn't come from money, wasn't surrounded by people who understood money. He didn't know enough about money to even ask the right people the right questions. "It was," he says, "paralyzing, debilitating." Gerut, 35, shakes his head when he looks back at that old portfolio and his own ignorance. Had he not wised up early in his big league career, done his homework and started managing his own money, who knows how much that particular portfolio would have crippled his post-playing funds? During parts of six seasons, Gerut was an American League Rookie of the Year candidate with the Indians in 2003 and a Comeback Player of the Year candidate with the Padres in 2008. In between and afterward were assorted knee problems, platoon roles, Minor League assignments and bench jobs that kept his career from being particularly lengthy or celebrated. Gerut, though, was an undeniably interesting player -- probably one of the few who subscribed to The Economist or immersed himself in textbook-sized biographies of political greats. His answers in interviews were always just a little more thoughtful, a little more insightful, and, yes, a little more wordy. When he announced his retirement in early 2011, he did so with a 231-word statement that was refreshingly honest.