Maestri made history in 2006 when he became the first Italian-born pitcher to be signed by a Major League organization (Chicago Cubs.).  Hailing from Cesena, the two-time All-Star represented his country by pitching in the World Baseball Classic in both 2006 and 2009.Spending five seasons in the Cubs organization, Maestri was used as both a starter and reliever, going 24-17 with a 3.75 ERA with 19 saves in 191 games.  In 2007 he earned a spot on the Midwest League All-Star team for Class-A Peoria, posting a 6-3 record with a 2.26 ERA and 12 saves, while averaging a strikeout per inning.  A year later, Maestri made the Florida State League All-Star team as a starter, going 5-3 with a 3.69 ERA for Class-A Advanced Daytona before being promoted.