Born on January 6th 1985 in Cesena. Right handed pitcher, he is under contract with the Chicago Cubs and rated by Baseball America number 23 (and the best overall ‘slider’) amongst the prospects of the organization. In the 2007 season he played for the Peoria Chiefs (Class A).
He was one of the 6 pitchers who entered the Italian Academy in 2003. He made his Serie A1 debut in 2005 for San Marino. In his rookie season he pitched in the 7 game Italian Baseball Series. Internationally he has participated in the AAA European (2003) and World (2002) Championships. He has made his debut for Team Italy in 2005 in a friendly match against the Torrington Twisters (USA).
He performed in the 2006 World Baseball Classic, in the 2007 European Championship in Barcelona and in the 2007 World Cup in Chinese Taipei, where he closed the game against Team USA striking out second baseman Nix on a 94 mile per hour fastball. Maestri has appeared in 13 games for the Italian National Team