3. Cliff Lee Part 1
The first time the Phillies made the move to acquire Cliff Lee, the Phillies were thinking back-to-back World Series. Lee finished the season third in the Cy Young voting and nearly beat the Yankees by himself in 2009.
What makes the move even better is the majority of the prospects did not pan out for Cleveland. Carlos Carrasco has finally turned a corner, but is currently injured and not active for the World Series. If he was healthy all season, he could be a Cy Young candidate and the World Series might be over already.
Jason Knapp the Phillies 10th ranked prospect, has not played since 2014, and never reached past Advanced-A in the Rangers organization. Jason Donald was the next big infielder expected to come through the Phillies system, but Jimmy Rollins and Chase Utley blocked the fourth ranked prospect from moving up. Donald played three seasons in Cleveland, but has not played for a major league organization since 2014.
Lou Marson appeared in eight games for the Phillies behind the plate, and hit a home run in his only game in 2008. With Carlos Ruiz winning the starting job for the long-term future, Marson went to Cleveland and appeared in 253 games over parts of five seasons. He hit .217 with 46 extra-base hits with the Indians, and last played for the Reds Double-A team in 2015.
Considering Lee helped lead the Phillies to a World Series appearance, you can deem the move a success. Young players were moved for talent at the right time, unlike the Oswalt, Pence, or Michael Young deals.