No. 5: Traded to Philadelphia
After back-to-back World Series appearances, the Phillies were the powerhouse of the National League. However, after losing to the Yankees in 2009, general manager Ruben Amaro, Jr. wanted to add another piece to the team to help them bring the championship trophy back to Philadelphia.
That move proved to be trading for one of the top pitchers in the American League since the turn of the century, Roy Halladay. He had already won one Cy Young award and had been in the top five for voting in each of the last four seasons. It seemed hard to outdo the Cliff Lee trade from the 2009 trade deadline, but Amaro did just that.
The biggest thing about the trade was that Halladay wanted to come to Philadelphia and win a World Series. The Phillies nearly acquired him at the trade deadline that year, but the deal never came together and they instead traded for Lee. Meanwhile, Halladay had to watch the 2009 playoffs from home. He told Sports Illustrated in an article after the trade that he couldn’t watch the World Series that year because the trade never came to be.
In return, Philadelphia sent Kyle Drabek, Michael Taylor and Travis D’Arnaud to the Blue Jays. In addition, Lee was traded to Seattle in exchange for J.C. Ramirez, Phillippe Amount, and Tyson Gillies. What could’ve happened that season with both Lee and Halladay in the rotation will forever be one of the biggest “what ifs” in Philadelphia sports, but Halladay soon proved himself more than worthy of the trade the next season.