The Phillies won the National League East divisional title each of the first three years of Amaro's tenure, appearing in the 2009 World Series and finishing with the best record in baseball during the and regular seasons (the latter, with 102 wins, their best record in franchise history). In , with the Phillies pitchers struggling despite being the defending World Series title holders, he traded for Cliff Lee and signed free agent Pedro Martinez, who contributed to the Phillies' return run to the World Series. In , Amaro traded for Roy Halladay but also dealt away Lee. In late July, when the Phillies were games behind the Atlanta Braves, he pulled off yet another crafty trade, acquiring Roy Oswalt and "triggering a late-season blitz to baseball's best record." Prior to the season, Amaro managed to convince Lee – then a free agent courting interest from the Texas Rangers and New York Yankees – to re-sign with the Phillies, joining a pitching rotation consisting of Halladay, Oswalt, Cole Hamels, and Joe Blanton. Commentators called it one of the best rotations ever assembled. Halladay, Oswalt, Lee, and Hamels were dubbed the '"Phantastic Phour"' by fans and the media. However, Amaro was criticized for giving a US$125 million 5-year contract extension to an already-ailing Ryan Howard in , which was regarded as highly unnecessary, because Howard was already signed through to the end of the season – by which time he would be 32 years old, which is "about the age at which teams start to worry about decline in big-bodied first-base/DH types."