Complex sentence: He was the general manager of four Major League Baseball teams, and guided teams to three World Series championships in his career: 1992 and 1993 titles with the Toronto Blue Jays, and a 2008 title with the Philadelphia Phillies.
Split into simpler sentences: He was the general manager of four Major League Baseball teams. He guided teams to three World Series championships in his career: 1992 and 1993 titles with the Toronto Blue Jays, and a 2008 title with the Philadelphia Phillies.