Phillies: Most impactful trade made with every team

Los Angeles Dodgers: Jimmy Rollins for Zach Eflin
"On December 19, 2014, the Philadelphia Phillies traded Jimmy Rollins and cash to the Los Angeles Dodgers for Tom Windle and Zach Eflin."
No trade is more impactful for a franchise than when you trade your all-time hits leader and the greatest shortstop in team history.
The Jimmy Rollins trade was a sign that the Phillies were seriously ready to move on and rebuild. They had moved other players like Shane Victorino and Hunter Pence, but trading a key piece of the 2008 team and handing the shortstop job over to Freddy Galvis was a sign of the times in Philadelphia.
Rollins was clearly at the end of his borderline Hall of Fame career coming off a career-worst .243 batting average. The former MVP and Gold Glove winner took his talents to Los Angeles and struggled just as much in 2015, seeing his average drop even more.
Thankfully the Phillies still got a very solid return for Rollins with pitcher Zach Eflin.
To get anything in return for Rollins at that point in his career was exceptional. If Eflin is to materialize into at the worst a quality number five pitcher, the Phillies made out ok. Eflin wasn’t even ranked in the Dodgers top-20 prospects at the time of the deal, but he’s shown flashes of being a quality starting pitcher for the Phillies over the last four years, including throwing two complete games in 2019.
Tom Windle, the ninth-ranked prospect in the Dodgers system, was the second player to come over in the deal, was in the Phillies farm system as recently as last season pitching for AAA Lehigh Valley. Philadelphia had transitioned him into a reliever, but he could never get his ERA below four. They released him in August and he was assigned to the Red Sox Low-A team at the age of 27.
Honorable Mention
August 7, 2014. The Philadelphia Phillies traded Roberto Hernandez to the Los Angeles Dodgers for Victor Arano and Jesmuel Valentin.