After taking over as GM the day after the Phillies World Series parade in 2008, Amaro oversaw the most successful era of Phillies baseball and traded for some of the biggest names in the game like Cliff Lee, Pedro Martinez and Roy Halladay. He assembled the Four Aces in 2011, brought in Hunter Pence and Raul Ibanez to bolster the outfield and saw a franchise-record 102 victories that season. Yet the party ended quickly, and much of it weighs on Amaro's shoulder. He signed Ryan Howard to a terrible contract in 2010, he traded away the entire farm system and tried to replenish it by trading Cliff Lee, he signed Jonathan Papelbon to the largest contract ever for a reliever… and he was out after seven years.
Pat Gillick gave credit where credit was due after the Phillies won the World Series: "This is Ed Wade's team." Burrell, Utley, Hamesl, Howard, Myers, Victorino. Wade drafted the core of the most successful Phillies teams in franchise history. He signed Jim Thome and traded for Bobby Abreu, two cornerstone players. During his tenure though, he never made the playoffs. It seemed he couldn't put the final pieces together, and the fans let him know after attendance dropped by over half a million in the second year of the new ballpark Wade helped build. The fans wanted a playoff appearance, and Wade never delivered on that end.
Banner was not a people person during his tenure in Philadelphia. He was a brutal negotiator that identified as "the bad guy" who rarely spent money on free agents. Banner also oversaw the rebuild of the franchise and a successful run for the Eagles, who reached the playoffs 11 times during his 16 years. He was one of the first to master the salary cap (something he passed along to Howie Roseman) and re-signed young players early on. He helped draft 20 Pro Bowlers with Andy Reid, and he traded for the best tackle in Eagles history, Jason Peters. Banner rubbed many people the wrong way, but he helped create sustainable success in Philadelphia while bringing in incredible players.
King was tasked with the difficult job of maintaining the peace between Larry Brown, Allen Iverson and Pat Croce before he was named Sixers president in 2003. It didn't start off well after he awarded big contracts to Kenny Thomas and Sam Dalembert, and he constantly struggled to find pieces to put around Iverson, including an aging Chris Webber. He ultimately traded him to Denver after pressure from new owner Ed Snider, and he was out of the Sixers organization the next year. King was in a precarious situation his entire career in Philadelphia, and he worked with what he had. Credit is due with his construction of the 2001 Finals team, acquiring Dikembe Mutombo at the trade deadline to sure up the backcourt. He grabbed Kyle Korver from the Nets, selected Andre Iguodala in 2004 and drafted Lou Williams and Thad Young. King just never found that perfect fit during the Iverson years.