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RANK WEEK: Top 10 Philadelphia sports “What if?” moments

July 18, 2025

After four days of Rank Week, you've read, watched, and listen to each team's Top 10 "What if?" scenarios. Finally, we rank them all together. Here are the Top 10 Philadelphia sports "What if?" moments:

10. What if… the Phillies didn’t trade Cliff Lee after signing Roy Halladay?
On December 16, 2009, the Phillies went all in by acquiring Cy Young winner, Roy Halladay, from the Toronto Blue Jays in exchange for a trio of prospects, headlined by Kyle Drabek.
But on the same day, the Phillies sent 2009 ace, Cliff Lee, who they acquired just a few months prior, to the Seattle Mariners to “restock the farm system”. The Phillies received, among others, Philippe Aumont, in the deal.
Both Halladay...

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