The Philadelphia Phillies have made some questionable free agent signings over the last couple of years. While the most recent signings are fresh in our memories, what are some other bad decisions the Phillies have made with their free agent additions since 2018? Didi Gregorius, SSThe Phillies signed Didi Gregorius to a one-year, $14 million contract in December 2019. Jeurys Familia, RHPJeurys Familia signed with the Phillies before the 2022 season to a one-year, $6 million contract. Nick Castellanos, OFThe Phillies added outfielder Nick Castellanos on a five-year, $100 million contract in March 2022.