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 MLB 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).
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 Triple-A 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.[1][2]
Penn was traded to the Florida Marlins on April 1, 2009 in exchange for infielder Robert Andino.[3] After a bad outing on June 3, the Marlins designated Penn for assignment. He cleared waivers and was assigned to the Triple-A New Orleans Zephyrs. On November 9, the Marlins purchased his contract from New Orleans and added him to their 40-man roster.
Penn was waived by the Marlins during the 2010 spring training and claimed by the Pittsburgh Pirates,[4] making their opening day roster.[5] He was designated for assignment on April 12, 2010 after giving up 8 runs in 2+1⁄3 innings pitched over 3 games,[6] accepting an assignment to the Triple-A Indianapolis Indians.
Penn's contract was sold to the Chiba Lotte Marines of Nippon Professional Baseball during the 2010 season. He helped the Marines win the 2010 Japan Series, starting and winning Game 5 of the series. Penn did not pitch during the 2011 season after undergoing elbow surgery.[7]
Penn played for the Bridgeport Bluefish of the Atlantic League of Professional Baseball in 2013.
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