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

Two World Series championships and franchise legends like Mike Schmidt and Richie Ashburn will earn their fair share of glory. Memories of great trades to land Steve Carlton and Roy Halladay will live forever.

What about the not so great trades? The Philadelphia Phillies were infamously the first professional sports franchise to reach 10,000 losses. They encountered their fair share of blunders to get there.

Worst Trades in Phillies History

Phillies fans will adamantly demand 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.

Giving up on prospects can lead to the feeling of regret for the one that got away. Phillies fans consider the trades that sent away Ryne Sandberg and Ferguson Jenkins some of the worst decisions the organization has ever made.

Decades have gone by, but the deals still come up in barroom conversations in the City of Brotherly Love. The revisionist history leads to fascinating speculation about what could’ve been. 

Best Trades in Phillies History

Some of the same names that appeared on 11 Worst Trades in Philadelphia Phillies History also appeared on 11 Best Trades in Philadelphia Phillies History from 97.5 The Fanatic.

The Fightin’ Phils developed a strange knack for acquiring talent in effective deals and handing away that talent in future trades.

The top two Phillies trades included impactful pieces of the 1980 and 2008 World Series winners.

Related Content: 11 Best Trades in Philadelphia Phillies History

Worst Trades in Phillies History

  • 11. Von "541" Hayes

    December 9, 1982
    Phillies Get: Von Hayes
    Cleveland Indians: Manny Trillo, George Vukovich, Julio Franco, Jay Baller, Jerry Willard

    Pete Rose coined the infamous “541” nickname when the Phillies acquired Von Hayes in 1982. Paul Owens gave up the haul for someone he thought was worth it.

    Hayes might’ve clicked better with the Philadelphia fan base without the high expectations. He had a decent nine-year stretch, and he even finished eighth in MVP voting after a career season in 1986. However “541” was all anybody focused on.

    Manny Trillo bounced around the majors in his later years after the trade. George Vukovich, Jay Baller, and Jerry Willard didn’t ultimately make the Phillies regret their decision.

    Julio Franco somehow haunted the Phillies into the early 2000s. He stuck with the Braves into his 40s and retired in 2007 after 23 MLB seasons with eight teams.

    Phillies Worst Trades: Von Hayes

  • 10. Saying Goodbye To Chase Utley

    August 19, 2015
    Phillies Get: Darnell Sweeney, John Richy
    Los Angeles Dodgers Get: Chase Utley, cash

    The Phillies kept franchise heroes like Chase Utley around a little too long after 2011. They probably could’ve gotten a better return a year or two sooner.

    Utley’s knees had pushed him out of his prime by 2015. Darnell Sweeney hit under the Mendoza line in his only 37 major league games, all with the Phillies. John Richy never made it to the show.

    Was Utley in his prime when he went to Los Angeles? No, but they certainly didn’t expect to get 386 games out of a veteran with a World Series pedigree.

    Acquiring one of the best heads-up players in MLB history helped the Dodgers win four NL West pennants in Utley’s four seasons, even if he wasn’t the main cause of their success.

    Phillies Worst Trades: Jimmy Rollins and Chase Utley

  • 9. A Sharp Turn And A Twist Of Irony

    December 20, 2002
    Phillies Get: Kevin Millwood
    Braves Get: Johnny Estrada

    Johnny Estrada filled in well for MIke Liberthal in 89 games in 2001. However, it made sense to trade a young catcher who wasn’t going to overtake an established veteran in front of him.

    Acquiring Kevin Millwood from the Braves looked like it could help solidify the starting staff of a team that had just signed Jim Thome.

    The league finally had to take the Phillies seriously in 2003, and Millwood got the city excited with a no-hitter at Veterans Stadium less than a month into his tenure. Lieberthal legitimized the trade with a career best .313 average.

    The outlook on the trade took a fast, wild turn in 2004. Millwood struggled at the top of the rotation in his final season with the Phillies. The fan base made him the whipping boy of an underperforming squad.

    Estrada, meanwhile, earned a National League All-Star appearance and the Silver Slugger honors. Lieberthal started declining at age 32.

    A frustrating Phillies team took heat for their inability to drive in runners in scoring position. Estrada ironically excelled with a newfound strength in that very category.

    Estrada only spent one more season with the Braves after 2004. He was out of the majors by 2008. However, Phillies fans can never fully shake the irony of a trade that looked one-sided in their favor before the pendulum swung so drastically.

    Phillies Worst Trades: Kevin Millwood

  • 8. The Flyin' Hawaiian

    July 31, 2012
    Phillies Get: Josh Lindblom, Ethan Martin, player to be named later (Stefan Jarrin)
    Los Angeles Dodgers Get: Shane Victorino

    The Phillies waited too long to send Chase Utley to the Dodgers after the fallout from the 2011 playoff loss. They didn’t wait long enough to send Shane Victorino.

    The Flyin’ Hawaiian was a dynamic talent who won two Gold Gloves in Philadelphia. He was only 31 years old at the time of the trade. The Phillies simply didn’t get enough in return for a player with plenty of good baseball left.

    Ethan Martin made only eight career starts, and Stefan Jarrin never played in the major leagues. Josh Lindblom had some potential as a reliever, but the Phillies only kept him for the remainder of the 2012 season.

    Victorino celebrated his second World Series the next season as a member of the Boston Red Sox.

    Shane Victorino, Philadelphia Phillies

  • 7. Mysterious Medicals For Freddy Garcia

    December 6, 2006
    Phillies Get: Freddy Garcia Chicago
    White Sox Get: Gio Gonzalez, Gavin Floyd

    The Phillies traded two pitching prospects to the White Sox for Freddy Garcia entering the 2007 season. 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.

    Lauded top prospect Gavin Floyd never developed well in the Phillies system. He recovered for a career as a serviceable starter in the middle of a solid major league rotation.

    It was Gio Gonzalez who really irked Phillies fans who looked back on the trade.

    The Phillies lost in the 2011 MLB Playoffs and quickly realized their lack of a farm system. Meanwhile, the Washington Nationals seized control of the NL East.

    Gonzalez broke out in 2012 to help put the Nats on the map. He finished third in NL Cy Young voting in a career season.

    He cooled off as an ace, but he still helped anchor the Washington rotation for a long stretch of his MLB career.

    The Freddy Garcia trade strangely landed the Phillies Tadahito Iguchi in an indirect handshake agreement between Kenny Williams and Pat Gillick later in the 2007 season. Phillies Worst Trades: Freddy Garcia

  • 6. An Unnecessary Unload: Cliff Lee Part I

    December 16, 2009
    Phillies Get: Phillippe Aumont, Tyson Gillies, J.C. Ramirez
    Seattle Mariners Get: Cliff Lee

    The Phillies acquired Cliff Lee in July 2009 in one of the best deals in franchise history. They dealt him to the Seattle Mariners for three unimpactful prospects less than six months later.

    Ruben Amaro Jr. acquired Roy Halladay on the same day, but he shifted his eyes to the future after giving up top pitching prospect Kyle Drabek. The moves were interconnected, but trading for Halladay didn’t directly require trading away Lee.

    The nonchalant lefty helped the Texas Rangers to an appearance in the 2010 World Series with another outstanding postseason run. 

    J.C. Ramirez later bounced around the majors as a reliever, but he only pitched in 18 games with a 7.50 ERA for the Phillies.

    Tyson Gillies never played a big league game, and Phillippe Aumont disastrously struggled to harness a loaded arsenal of pitches. He floated back and forth from Lehigh Valley from 2012-2016 without any substantial major league success.

    Lee stunned the world, especially the New York Yankees, when he reunited with the Phillies entering the 2011 season.

    Phillies Worst Trades: Carlos Ruiz and Cliff Lee

  • 5. Grover Cleveland Alexander Leaves The Baker Bowl

    December 11, 1917
    Phillies Get: Mike Prendergast, Pickles Dillhoefer, $55,000
    St. Louis Cardinals Get: Grover Cleveland Alexander, Bill Killefer

    It requires a look deep into the history books, but a pitcher as successful as Grover Cleveland Alexander commands close inspection.

    Alexander pitched over 300 innings (not just over 200, over 300) in all seven of his seasons in Philadelphia from 1911-1917. He helped the Phillies to the 1915 National League pennant as a Baker Bowl legend. It didn’t convince the organization to keep him.

    World War I forced MLB organizations to make some tough decisions. The Phillies sent Alexander to the Chicago Cubs for two players and cash in 1917 with the expectation he might be drafted into the war.

    Mike Prendergast pitched only 38 games for the Phillies. Pickles Dillhoefer’s name is more significant than his eight-game stint with the Phillies. Alexander played 12 more major league seasons with the Cubs and the St. Louis Cardinals.

    He stopped back in Philadelphia for a cup of coffee with the Phillies in 1930 before he retired.

  • 4. Losing Curt Schilling

    July 26, 2000
    Phillies Get: Vicente Padilla, Omar Daal, Travis Lee, Nelson Figueroa
    Arizona Diamondbacks Get: Curt Schilling

    The move to land Curt Schilling for Jason Grimsley in 1992 looked like a steal. The fortune caught up to the Phillies, as the Diamondbacks made one of the best trades in their franchise history.

    The Phillies spiraled downward into futility after 1993 as Schilling rose into his prime. By 2000, it became obvious that they couldn’t keep their ace any longer.

    Schilling won two World Series and finished second in Cy Young voting three times after the Phillies traded him at age 33. He continued to develop his reputation as one of the fiercest competitors in all of sports.

    He and Randy Johnson formed an unhittable duo on the memorable ride to the World Series in 2001. Arizona’s victory over the New York Yankees came with all of America watching just weeks after the 9/11 tragedy. The pair of aces split the MVP.

    Former second-overall pick Travis Lee could’ve developed as the centerpiece, but he never lived up to his draft status. Omar Daal and Nelson Figueroa didn’t amount to much with the Phillies.

    Former GM Ed Wade did land Vicente Padilla in the trade. The Nicaraguan righty spent six seasons in the middle of the starting rotation for Philadelphia. He ended up pitching 14 MLB seasons.

    Phillies Worst Trades: Curt Schilling

  • 3. Wondering What Could've Been

    April 21, 1966
    Phillies Get: Adolfo Phillips, John Herrnstein
    Chicago Cubs Get: Ferguson Jenkins, Bob Buhl, Larry Jackson

    The Phillies brought Ferguson Jenkins up to the majors for seven appearances in 1965, but they didn’t give the young right-hander much of a chance in 1966.

    A franchise nearing 100 years of existence in brutal futility just two years removed from the epic collapse of 1964 traded away a future Hall of Famer for two players who barely made a footnote in Phillies history.

    Jenkins won the 1971 NL Cy Young as the highlight of his prime seasons with the Cubs. He also spent time with the Texas Rangers and the Boston Red Sox as part of a 19-year career.

    Philadelphia was left to wonder what could’ve been.

    Phillies Worst Trades: Ferguson Jenkins

  • 2. A Memorable Sendoff & A Forgettable Trade

    July 31, 2015
    Phillies Get: Jered Eickhoff, Jorge Alfaro, Nick Williams, Matt Harrison, Jake Thompson, Alec Asher
    Texas Rangers Get: Cole Hamels, Jake Diekman

    Professional sports is an unforgiving business. Athletes don’t usually know when their last game in a particular uniform will come.

    Cole Hamels, however, was all but certain the Phillis would move him before the MLB Trade Deadline in 2015.

    He might’ve known that July 25, 2015 would be the last day he’d start a game for the Phillies, but he didn’t know about the unforgettable farewell that was about to take place.

    The 2008 World Series MVP threw his only career no-hitter at Wrigley Field. His teammates swarmed him in an emotional moment in Phillies history.

    The goodbye, unfortunately, became way more significant than the return package in the ensuing trade. Hamels was only 31, and he pitched four more substantial MLB seasons. 

    The early return on Jered Eickhoff, Jorge Alfaro, and Nick Williams didn’t look too bad. However, none of the six players the Phillies acquired stuck around too long.

    Making matters worse, Ruben Amaro Jr. also sent Jake Diekman to Texas. A reasonable case can be made that the journeyman reliever alone has provided more value than any of the six players in the return package.

    That’s right. The Phillies would’ve lost the trade even if Hamels wasn’t part of it.

    Cole Hamels, Philadelphia Phillies

  • 1. An Easy Choice In The Top Spot

    January 27, 1982
    Phillies Get: Ivan de Jesus
    Chicago Cubs Get: Ryne Sandberg, Larry Bowa

    Paul Owens and Bill Giles made one of the worst mistakes in franchise history in 1982. Trading Larry Bowa was never going to make Philadelphia happy to begin with. He was the scrappy catalyst of the 1980 World Series team, a five-time All-Star, and a player who identified with the city like very few others could.

    The Phillies wouldn’t let sentimentality keep a 36-year-old around. They sent Bowa to the Cubs for a reunion with former manager Dallas Green.

    Green insisted that the Phillies included a middle infielder as a pot sweetener. Ryne Sandberg spent 15 seasons with the Cubs. He made 10 consecutive All-Star appearances from 1984-1993 and established himself as one of the best players in the history of a storied franchise. The accolades landed him in the Hall of Fame.

    The Phillies only gave him six plate appearances in 13 major league games before the deal. A bizarre twist of fate landed him back in Philadelphia as the manager from 2013-2015 during a forgettable era.

    Ivan de Jesus played 158 games in 1983 for a team that advanced to the World Series. However, his underwhelming play in three seasons only poured salt on the wound of the worst trade in Phillies history.

    Phillies Worst Trades: Ryne Sandberg

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