Born in Santee, California, Penn was drafted by the Baltimore Orioles in the 5th round of the 2002 Major League Baseball Draft. He made his major-league debut in 2005, when he made eight starts with the Orioles, compiling a 3–2 record with a 6.34 ERA. At the time of his callup Penn was the youngest player in the Major Leagues (20 yrs, 7 months).\n', '

In May 2006, he suffered appendicitis after being called up by the Orioles and missed several months while recovering from it. He went 7–4 with an ERA of 2.26 through 14 starts for the Class AAA Ottawa Lynx in 2006 and was called up to Baltimore again when the major league rosters expanded on September 1. He made his first start of the season for Baltimore on September 3 against the Oakland Athletics; he gave up eight runs in two-thirds of an inning, for an ERA of 108.00, and took the loss.\n', '

Penn was traded to the Florida Marlins on April 1, 2009 in exchange for infielder Robert Andino.\n', '

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