On January 9, 2009, The Boston Red Sox finalized a deal with Brad Penny for a one year contract worth $5 million dollars. The contract also has incentives which could add an additional $3 million to the contract. In 2008, Penny had a record of 6-9 with a 6.27 earned run average.ESPN.com: Penny deal with Red Sox official (January 9, 2009)

On July 8, 1999, Penny was traded to the Florida Marlins. After finishing the 1999 season with the Marlins' minor league team, Penny was called up to make his MLB debut with the Marlins on April 7, 2000. He played a total of 23 major league games that season, pitching in 119.7 games and finishing with a 4.81 earned runs average.MLB.com Brad Penny Bio

Penny continued on the full roster of the Marlins for the next three and a half seasons, including in 2003, where Penny made his first post season appearance. Penny won the 2003 World Series with the Marlins over the New York Yankees.MLB.com Brad Penny Bio

On July 30, 2004, Penny was traded to the Los Angeles Dodgers as part of a six player trade. Penny missed the rest of the 2004 season and the beginning of the 2005 season with a bicep injury.MLB.com Brad Penny Bio

In 2006, Penny was selected for his first of two MLB All-Star Games. He was again selected for the All-Star Team in 2007, where he was also third in voting for the Cy Young Award, given to the best major league pitcher.