Complex sentence: He had been the owner of the Pawtucket Red Sox, the Triple-A International League affilitate of the Boston Red Sox since 1977, and a two-time winner of the International League Executive of the Year award (1978,1999).
Split into simpler sentences: He had been the owner of the Pawtucket Red Sox, the Triple-A International League affilitate of the Boston Red Sox since 1977. He was a two-time winner of the International League Executive of the Year award (1978,1999).