The professional sports franchise with the longest tenure in one city with one name has its fair share of history.

Any list of all-time Philadelphia Phillies accomplishments can glorify big names like Mike Schmidt, Pete Rose, or Richie Ashburn. However, some of the most impactful acquisitions have come from the best trades in Phillies history.

Best Trades in Phillies History

The Fightin’ Phils have traded for their all-time wins leader, one of the fiercest competitors in MLB history, and the man responsible for clinching the 2008 World Series.

Legends like Steve Carlton and Roy Halladay will persist in the hearts of Philadelphia fans, but what about the general managers who made the moves happen?

Paul Owens gets the bulk of the glory as the architect of the 1980 World Series. However, it was John Quinn who landed Steve Carlton in his final deal with the Phillies.

Ruben Amaro Jr. unceremoniously left the front office, but he also assembled the best pitching staff in Phillies history.

One forgotten era in Phillies history also included trades for some of the best-kept secrets before they became star players. The decade following the 1993 World Series wasn’t pretty, but imagine how much worse it would’ve been if the Phillies hadn’t traded for Curt Schilling or Bobby Abreu.

Worst Trades in Phillies History

The Phillies have made their fair share of blunders too. It was also bound to happen for a franchise that’s been around since 1883.

They infamously gave up too soon on Ferguson Jenkins. One of the most regrettable ones that got away was a throw-in sweetener in a deal with the Chicago Cubs. 

Related Content: 11 Worst Trades in Philadelphia Phillies History

Phillies fans will adamantly demand for the best deals every season leading up to the MLB Trade Deadline. However, they should also remember that these deals can go unimaginably far in either direction.

Best Trades in Philadelphia Phillies History

  • 11. The Hefty Lefty

    Phillies Get: Jose Alvarado
    Los Angeles Dodgers Get: Garrett Cleavinger (from Phillies)
    Tampa Bay Rays Get: Dillon Paulson, player to be named later (from Dodgers)

    Philadelphia teams seem like they’re always the ones who give up too soon and trade talented young players who haven’t reached their full potential. Jose Alvarado reversed the trend.

    The Hefty Lefty accepted a demotion to the minors in 2022 and recreated a power sinker. He returned to the majors and stepped into one of the most important high-leverage roles on the way to a World Series appearance in 2022.

    He’s now one of the strongest power arms at the back of the Phillies bullpen.

    Garrett Cleavinger still has the potential to match Alvarado, but the Phillies got the best immediate return from the trade.

    Best Trades, Phillies History: Jose Alvarado

  • 10. An Apology From The White Sox?

    July 27, 2007
    Phillies Get: Tadahito Iguchi
    Chicago White Sox Get: Michael Dubee

    What did the Phillies send to the White Sox for a lineup regular with .278 and .281 respective batting averages in his only two full MLB seasons? Michael Dubee, pitching coach Rich Dubee’s son, a Single A pitcher who ultimately never made it to the major leagues.

    Why would Chicago GM Kenny Williams trade Tadahito Iguchi? It makes a little more sense in the big picture. The Phillies also acquired Freddy Garcia from the White Sox the previous offseason. Landing an expected ace was a big part of the reason Jimmy Rollins spoke so confidently about “the team to beat” in the NL East.

    It turned out to be one of the worst trades in franchise history. Garcia pitched 11 games in his only season in Philadelphia. The injuries that kept him off the mound very well might’ve existed before the trade.

    “That was a gift to Pat Gillick because Kenny Williams felt bad for (trading) Freddy Garcia (to the Phillies)… It was like two baseball men doing each other a solid.” -Jim Salisbury

    According to Gillick’s former assistant GM, The Phillies essentially picked up Tadahito Iguchi as an apology from Kenny Williams and the White Sox.

    “I’ve got to believe that they’re had to be something to that (granting the favor) because there was some question about the medicals on Freddy that we checked out, but (the information was) maybe a little shady.” –Ruben Amaro Jr.

    Iguchi hit .304 in 45 games to finish the 2007 season. He played an everyday role for the first month while Utley sat. He later moved into a bench role after the everyday second baseman reentered the lineup.

    Iguchi famously slid into home on Utley’s walk-off hit in an August thriller against the New York Mets that helped the historic NL East comeback. Best Trades, Phillies History: Tadahito Iguchi

  • 9. A 43-Year-Old From Waivers

    August 19, 2006
    Phillies Get: Jamie Moyer
    Seattle Mariners Get: Andy Baldwin, Andrew Barb

    The MLB Trade Deadline used to allow for waiver deals during the month of August. Before the overdue rule change, Pat Gillick landed Jamie Moyer for two minor leaguers in August 2006.

    Moyer never had head-turning velocity in his previous 20 seasons of major league experience, so his age didn’t factor into his ability to pitch much. He began his stint in Philadelphia at age 43 and remarkably made 118 starts in five seasons.

    The local kid from Souderton and Saint Joseph’s University became one of the feel-good stories of the 2008 World Series. Neither Baldwin nor Barb ever played in an MLB game.

    Best Trades, Phillies History: Jamie Moyer

  • 8. Saying Goodbye To A "Can't Miss" Prospect

    February 7, 2019
    Phillies Get: J.T. Realmuto
    Miami Marlins Get: Sixto Sanchez, Jorge Alfaro, Will Stewart, international bonus slot money

    The class of free agents entering the 2019 season forced a domino effect on the entire sport. The Phillies were desperate for a superstar to reestablish themselves as a contender after a long period of dormancy.

    They lured Bryce Harper by trading for the best catcher in baseball. Matt Klentak sent stud pitching prospect Sixto Sanchez to the Marlins for J.T. Realmuto.

    Realmuto became a key piece in the miracle ride to the World Series in 2022. Sixto Sanchez had drawn comparisons to Pedro Martinez, but injuries derailed the early years of his career.

    Stewart never made it to the major leagues. Alfaro spent some serviceable seasons with the Marlins, but he never approached the caliber of Realmuto.

    Best Trades, Phillies History: J.T. Realmuto

  • 7. Clifton Phifer Lee (Part I)

    July 29, 2009
    Phillies Get: Cliff Lee, Ben Francisco
    Cleveland Indians Get: Carlos Carrasco, Lou Marson, Jason Knapp, Jason Donald

    The chatter leading up to the MLB Trade Deadline in 2009 focused on Roy Halladay. Could the Phillies land the best pitcher in the game and repeat with another World Series? 

    Instead, Ruben Amaro Jr. traded for Cliff Lee. The nonchalant Arkansas native looked effortless and unaffected by the pressure of the MLB postseason during a run to the World Series in 2009.

    The rest of the starting rotation struggled to make it through a deep playoff run. Lee won both of his starts against the New York Yankees, but the Phillies lost in six games.

    The Phillies missed out on a long career from Carlos Carrasco. However, it’s all relative to the risk of aggressive trade deadline spending in a window of World Series contention. 

    Although the trade only kept Lee in Philadelphia for a few months, the instant dynamic with the fan base played a major factor in convincing him to sign with the Phillies before the 2011 season.

    Best Trades, Phillies History: Cliff Lee

  • 6. A New Uniform Can Change An Attitude

    June 18, 1989
    Phillies Get: Lenny Dykstra, Roger McDowell, Tom Edens
    New York Mets Get: Juan Samuel

    It’s funny how a new uniform can change the fans’ attitude about a guy. Phillies fans hated Lenny Dykstra as a member of the Mets. Nails was the grinder who got under opponents’ skin on the way to a World Series in 1986.

    His gritty style transferred over with a division rival after the deal. Dykstra hit over .300 in three of his first four seasons in Philadelphia, and he became a major catalyst for the 1993 National League champs. 

    Roger McDowell also spent time at the back end of the bullpen in parts of three seasons. He saved 44 games for the Phillies before they traded him again in 1991.

    Juan Samuel had some good seasons with the Phillies in the early part of his career. However, he only played 86 games for the Mets after the trade before moving to five other MLB teams to finish his career.

  • 5. Unknown Youngster Bobby Abreu

    November 18, 1997
    Phillies Get: Bobby Abreu
    Tampa Bay Devil Rays Get: Kevin Stocker

    The Phillies swindled the Tampa Bay Devil Rays in 1997 when they acquired 23-year-old Bobby Abreu after just 64 career major league games. 

    Say what you want about Abreu. His demeanor never clicked in Philadelphia. He wasn’t a great outfielder (although he strangely won a Gold Glove in 2005). The decision to trade him for a minimal return in 2006 proved to be addition by subtraction. 

    Don’t let that make you forget his offensive production. 

    He sits 11th in Phillies history with 195 home runs and seventh in stolen bases with 254. His outstanding .303/.416/.513 slash line would make modern MLB front offices gush.

    Stocker helped the Phillies to the World Series in his rookie season in 1993, but he only played three more MLB seasons after the deal. He hit .237 collectively with the Devil Rays and the Anaheim Angels.

    Best Trades, Phillies History: Bobby Abreu

  • 4. The Future Ace

    April 2, 1992
    Phillies Get: Curt Schilling
    Houston Astros Get: Jason Grimsley

    The Baltimore Orioles and the Houston Astros couldn’t unlock Curt Schilling’s talent early in his career. He hit his stride after a deal to the Phillies in 1992. 

    Schilling established himself at the top of the rotation for the 1993 National League champions. He became the unquestioned ace during the mid and late 1990s, but the fading talent around him ultimately led to his departure.

    The Phillies enjoyed the benefits of an excellent talent for nine seasons, but they let him get away to win three World Series in two other uniforms.

    Grimsley pitched in the majors for 12 more seasons. He became a respectable journeyman reliever, but his accomplishments pale in comparison to Schilling.

    Best Trades, Phillies History: Curt Schilling

  • 3. A Philadelphia Legend

    December 16, 2009
    Phillies Get: Roy Halladay, cash
    Toronto Blue Jays Get: Kyle Drabek, Michael Taylor, Travis d’Arnaud

    The prospect experts loved Kyle Drabek. It seemed daring to deal a top young pitcher with tremendous potential, but Roy Halladay was available.

    Ruben Amaro Jr. landed the long-time Blue Jays ace at age 32. Halladay announced his unrelenting mission for dominance with a perfect game less than two months into his Phillies tenure.

    He only started 108 regular-season and playoff games in parts of four seasons for Philadelphia. However, two elite seasons in 2010 and 2011 and his frightening competitive spirit put him in franchise folklore.

    Drabek never spent a full season in an MLB starting rotation. He demonstrated how uncertain prospect projections can be and the value of aggressive moves for teams with a window for World Series contention. 

    While d’Arnaud turned into a solid major leaguer, the Phillies will never regret sending him away.

    Best Trades, Phillies History: Roy Halladay

  • 2. Perfection in 2008

    November 7, 2007
    Phillies Get: Brad Lidge, Eric Bruntlett
    Houston Astros Get: Michael Bourn, Geoff Geary, Mike Costanzo

    A monstrous three-run blast from Albert Pujols in the 2005 NLCS supposedly ruined the psyche of All-Star closer Brad Lidge.

    Former Phillies GM Ed Wade dealt Lidge to the Phillies in the deal that catapulted them to their second World Series. Pat Gillick sent back a package centered around Michael Bourn.

    Lidge’s glory didn’t last long in Philadelphia. He blew 11 saves in 2009 and never regained a rhythm afterwards.

    However, 48 saves in 48 chances had already solidified his place in franchise history. The Phillies wouldn’t have won the World Series in 2008 without Brad Lidge. Eric Bruntlett also played a solid role as a utility man and defensive replacement.

    Bourn became an excellent base stealer for the Astros. He stole 61 in 2009, 52 in 2010, and 61 in 2011. He carved out a solid 11-year career.

    Geary spent two seasons with the Astros. Costanzo only played 17 career MLB games.

    Best Trades, Phillies History: Brad Lidge

  • 1. Landing Lefty

    February 25, 1972
    Phillies Get: Steve Carlton
    St. Louis Cardinals Get: Rick Wise

    Rick Wise made his first of two MLB All-Star teams in 1971 in the last of his seven seasons in Philadelphia. He’ll never have much association in franchise history for that because fans remember his name as the guy the Phillies traded for Steve Carlton.

    Carlton had developed into a 20-game winner early in his career with the Cardinals, but John Quinn stole him in 1972. 

    Lefty came out fast with a 27-10 record and a 1.97 ERA in his first season with the Phillies. He won the first of his four CY Youngs and laid the groundwork to become the best pitcher in franchise history.

    Wise pitched well in two seasons with the Cardinals. He hung around for nine more years in the majors after leaving St. Louis.

    The Phillies weren’t worried about what they gave up. What they got back was plenty to keep them happy.

    They immortalize Steve Carlton with a statue outside Citizens Bank Park.

    Best Trades, Phillies History: Steve Carlton

  • 97.5 The Fanatic

    Watch Kincade & Salciunas on the 97.5 The Fanatic YouTube page for discussion about the latest breaking sports news in Philadelphia.


Sign me up for the 97.5 The Fanatic email newsletter!

Become a Fanatic MVP to get the latest info on the Philly Sports landscape, plus access to exclusive content and member-only contests.

By clicking "Subscribe" I agree to the website's terms of Service and Privacy Policy. I understand I can unsubscribe at any time.