I like trades and I like dates. What better time than the beginning of the season to put together a list of the best trades in Phillies history. Anytime you see a list like this, Steve Carlton is at the top. I figured I would do something different and put them in order. Here are the top 15 trades in Phillies history starting back over 100 years ago, because that’s fun…
December 26, 1917 – Cy Williams from the Cubs for Dode Paskert
Baseball during World War 1 wasn’t known for the long ball. In that time playing for the Cubs, Cy Williams would hit 34 HRs in his 6 Chicago seasons. That’s when the Cubs decided to trade him to the Phillies for 36-year-old Dode Paskert. Dode would hit 10 HRs over his career in Chicago before retiring in 1921. Those roaring 20s though brought the long ball to baseball and Cy Williams brought it to Philadelphia, hitting 217 HRs over the next decade including a league leading 41 in 1923. He was the NL’s career HR leader while he played until being passed by Rogers Hornsby in 1929. He is known to have been the muse for the invention of the shift since he could do nothing but pull the ball to right.
November 17, 1959 – Johnny Callison from the White Sox for Gene Freese
In 1959, Gene Freese led all NL 3B in one major category: errors. Well, the White Sox just had to have him and sent 20-year-old right fielder Johnny Callison to Philadelphia to get him. While Freese would only spend one season on the South Side, Callison would spend the next decade in Philadelphia becoming a 4x All-Star and even earning runner-up for MVP in the memorable (for the wrong reasons) 1964 season.
December 5, 1963 – Jim Bunning (and Gus Triandos) from the Tigers for Don Demeter and Jack Hamilton
Jim Bunning had a great 9 years in Detroit including leading the league in wins, strikeouts, and innings pitched on different occasions. At 31 though, the Tigers decided to move on from Bunning in a search for a true CF. Bunning apparently took this personally. After a mediocre last season in Detroit, Bunning went off for the Phillies racking up 30.3 WAR in 4 seasons which included a perfect game in 1964 and a runner-up Cy Young finish in 1967.1 Don Demeter, that true CF they were looking for, would play 2.5 seasons for the Tigers but only 129 games in center.
February 25, 1972 – Steve Carlton from the Cardinals for Rick Wise
Not much needs to be said about this one that hasn’t already been said. Carlton was already awesome for the St. Louis Cardinals and wanted more money. Owner Gussie Busch, despite being the scion of Anheuser-Busch, didn’t want to pay him and ordered the team to trade him. After throwing a no-hitter and hitting 2 HRs in the same game, Rick Wise looked like decent enough compensation. He wasn’t. Wise would pitch two good years for the Cards before being traded for two more good years of Reggie Smith, but none of that holds a candle to the 4 Cy Young awards won by Carlton in Philadelphia along with a World Series and the title of possibly the best lefty pitcher of all time.
June 2, 1989 – John Kruk (and Randy Ready) from the Padres for Chris James
John Kruk was a good hitting prospect who fell out of favor with the Padres due to a bizarre set of circumstances (detailed below). Their loss was the Phillies’ gain as Kruk would not only triple slash .309/.400/.461 for his Phillies’ career but would also become a local and national favorite due to his immaculate grooming and candid, hysterical personality. As for James, he was bad for the Phillies and would only last 87 games for the Padres before joining Sandy Alomar and Carlos Baerga in a trade to Cleveland for future Phillie killer Joe Carter.
June 18, 1989 – Lenny Dykstra (and Roger McDowell) from the Mets for Juan Samuel
Juan Samuel opened his career with 4 solid seasons for the Phillies, stealing a ton of bases and had a nice amount of XB power, but didn’t really walk and struck out a ton. Then his average plummeted and he was expendable. In a time before teams were turned off by strikeouts and turned on by walks, the Mets saw Samuel’s speed/power combo and decided they could use Samuel on the basepaths and in CF. Their own CF who had helped them win the WS in 1986 didn’t hit for any power at all and was about half the base stealer as Samuel. What Lenny Dykstra could do is walk and what he didn’t do was strikeout. The Dude’s first season with the Phillies was a huge 8.9 WAR season where he walked almost twice as much as he struck out. After 2 years of injuries, he broke out again with his monster 1993 season where he finished runner-up to Barry Bonds for MVP and led the Phillies to the World Series.2
April 2, 1992 – Curt Schilling from the Astros for Jason Grimsley
In 3 years with the Phillies, young Jason Grimsley was a starter, but not a very good one, walking more batters than he struck out. Despite this, the Houston Astros wanted him and traded a 25-year-old reliever to get him. Maybe the Astros should have tried starting Curt Schilling. Schilling was immediately great for the Phillies in ’92 and would pitch 31 superb innings in 4 playoff starts in ’93. Over his 8.5 year Phillies career, he would regularly rack up 200+ innings and even hit 300 Ks twice with a 3.35 overall ERA for the team before being traded to the Diamondbacks in 2000. Grimsley would pitch 15 years in MLB but was only even serviceable when he was using PEDs later in his career.
November 18, 1997 – Bobby Abreu from the Rays for Kevin Stocker
When the 1997 Expansion Draft came around, the Tampa Bay Rays needed a shortstop but none were left unprotected. Instead, they got creative to get 28-year-old Kevin Stocker from the Phillies. The Houston Astros had left top prospect Bobby Abreu unprotected that year (after 7 with the organization) and he was snatched up with the 6th overall pick. After the draft, Abreu was flipped straight up for Stocker. While Stocker is a great voice on Phillies radio, he had a solid glove and low-end bat that was out of the league within 3 seasons. Meanwhile, Abreu hit the ground running with the Phillies starting a string of 7 consecutive 5+ WAR seasons. In 8.5 years with the team he would hit nearly 200 HRs, 350 doubles, 250 SBs, have a .300+ batting average, and a .928 OPS. He is criminally underrated but was a great Phillie and they got him for almost nothing…sorry Kevin.
November 25, 2005 – Jim Thome to the White Sox for Aaron Rowand and Gio Gonzalez
This is the only trade on the list that should be considered addition by subtraction. Jim Thome had an amazing first 2 years with the Phillies after they signed him to a 6/$85m contract in free agency. In year 3 though, not only did he get hurt, but top prospect Ryan Howard made his debut as Thome’s replacement at first and won ROY. The Phillies had a log jam on their hands but were able to get a long-needed CF in Rowand and a top pitching prospects in Gio Gonzalez. Rowand would become a hero and Ryan Howard would win NL MVP the following year. Gonzalez would become a well above average pitcher beginning at exactly the time the Phillies would need him from 2010-2017…unfortunately they had already given him away for Freddy Garcia at that point. I always think about how much different the Phillies would have been if either they held on to Gio or the DH had come to the NL sooner. Imagine having Howard AND Thome???
August 19, 2006 – Jamie Moyer from the Seattle Mariners for 2 career minor leaguers
The 2008 World Champion Phillies did not have very good starting pitching. There was 227 great innings from Cole Hamels, 190 not great innings from Brett Myers, and 262 really bad innings from Kyle Kendrick and Adam Eaton. Joe Blanton and JA Happ gave 100 more. That’s only about 4/5 of the total starter innings though. 196 more went to Jamie Moyer who at 45 years old pitched to a 3.71 ERA and a team leading 16 wins. Considering the lack of depth, are the Phillies anywhere close to the playoffs if they didn’t make this waiver-trade deadline deal 2 years earlier? Moyer wouldn’t be on this list in the traditional sense, but everything that came after made it a steal.
July 29, 2009 – Cliff Lee (and Ben Francisco) from the Guardians for Jason Knapp, Carlos Carrasco, Jason Donald, and Lou Marson
It’s funny looking back on this that Jason Knapp was the big prize and Carrasco seemed like he might be a bust after his AAA results left much to be desired. Donald and Marson looked like solid regulars too. Only Carrasco did anything of note and Knapp blew out his arm and never made the majors. Meanwhile, Cliff Lee gave the Phillies 3 months of unbelievable production including the best World Series start you’ll ever see. Like idiots though, the Phillies traded him to Seattle in the offseason in a move that still makes me mad.
December 16, 2009 – Roy Halladay from the Blue Jays for Travis d’Arnaud, Kyle Drabek, and Michael Taylor
Roy Halladay was possibly the greatest pitcher of his generation but was wasting bullets in Toronto. He wanted to be a Phillie back in 2009, and the deal almost happened, but it was Cliff Lee coming to Philadelphia instead. A few months later, he got his wish and turned in two more vintage Halladay seasons that included a Cy Young, a runner-up (should have won) finish, a perfect game, a playoff no-hitter, and anchored one of the greatest rotations that ever existed. Even just those two seasons made the trade great considering only Travis d’Arnaud ended up having a solid career. Despite being a top prospect and carving up the minors, Drabek never hit in the majors. Taylor had himself an unbelievable 2009 and was flipped for another top prospect in Brett Wallace but never clicked in the majors.
February 7, 2019 – JT Realmuto from the Marlins for Jorge Alfaro, Sixto Sanchez, and Will Stewart
Sixto Sanchez was THE pitching prospect of the moment when this trade was made. He was nasty and looked to be getting better. The Marlins brought him up in 2020 and even though JT Realmuto had a good season in Philadelphia as the best catcher in baseball, Sixto was 21 and crushed it. And that was the last time anyone thought the Phillies may have lost this trade. Sixto wouldn’t be seen in the majors for 4 more years and by then there was nothing left after arm injuries took away what made him special. JT continued to be BCIB for 4-5 seasons with the Phillies and stabilized the Phillies lineup and rotation. What started as risky turned into an overwhelming win.
November 20, 2019 – Cristopher Sanchez from the Rays for Curtis Mead
It’s famous now for being such a landslide victory, but for anyone who doesn’t remember the history of this trade, the Phillies were getting laughed at for years as Sanchez stagnated and Mead flew up prospect charts. Once they both hit the majors though, everything changed. Sanchez is now one of the top five pitchers in baseball while Mead has been traded twice and has been fighting for at bats with both the White Sox and Nationals.
December 22, 2024 – Jesus Luzardo (and Paul McIntosh) from the Marlins for Starlyn Caba and Emaarion Boyd)
It’s still early, but even with the hindsight of the Sanchez-Mead trade fresh in this list’s mind Caba and Boyd are not expected to be able to serviceably hit MLB pitching. Meanwhile, Luzardo not only had a breakout season and received a huge contract extension, but showed out in the playoffs last year. He will be a high-end stalwart in the Phillies rotation for years to come. Caba doesn’t strike out and has a fantastic glove, but unless he drastically improves his hard contact, he will be nothing more than a 9-hole hitter at best and even that may never happen.
- I don’t know much about baseball in 1967, but the guy who won the award, Mike McCormick of the Giants, was worse than Bunning by a lot in every category except wins. The vote wasn’t close either. That was really the whole criteria back then apparently since the AL award went similarly with Jim Lonborg of the Red Sox nearly unanimously winning over Joe Horlen of the White Sox despite an ERA over a run higher. ↩︎
- Granted, Lenny was practically dripping steroids at the time, but so was most of baseball ↩︎
Philly Front Office 
Leave a comment