Which trades belong on the Mount Rushmore of Philly sports deals – for better or worse? Missing on a top draft pick is a setback, but a bad trade can set a franchise back for decades, potentially costing them a championship or leading to the departure of a future Hall of Famer. The stakes are high when evaluating trades, and in Philadelphia, teams have experienced both triumphs and failures in the trade market.

The Best Trades in Philly Sports History

Some trades in Philly’s history are so significant they seem untouchable on the city’s Mount Rushmore of trades. Looking back at the Phillies’ acquisition of Steve Carlton 50 years ago, let’s examine the deals that proved to be championship catalysts.

Wilt Chamberlain to the Philadelphia 76ers (1965)

Wilt Chamberlain is arguably the greatest basketball player of all time, and his acquisition by the Sixers was a game-changer. Philadelphia only gave up Connie Dierking, Paul Neumann, Lee Shaffer, and cash to bring Chamberlain home after the Warriors moved to San Francisco. Chamberlain led the Sixers to a title in 1967 alongside Hal Greer and Billy Cunningham, forming what many consider the best team in NBA history.

Steve Carlton to the Philadelphia Phillies (1972)

The Phillies acquired Steve Carlton from the Cardinals in 1972 for Rick Wise, dramatically altering the organization’s trajectory. The Phillies hadn’t won a pennant in over two decades and struggled to finish above .500. While it took a couple of seasons, Carlton’s arrival ushered in a winning era, culminating in the Phillies’ first World Series championship in 1980.

Bernie Parent Returns to the Philadelphia Flyers (1973)

Bernie Parent was already a good goaltender when he left the Flyers in 1971. However, his return from Toronto in 1973 transformed him into one of the best in the game. The Flyers traded goalie Doug Favell and a first-round pick to the Maple Leafs for Parent and a second-rounder. Parent’s impact was immediate, leading the Flyers to back-to-back titles in 1974 and 1975.

Moses Malone to the Philadelphia 76ers (1982)

Similar to the Chamberlain trade, acquiring Moses Malone provided the Sixers with the final piece needed for a championship. The Sixers sent Caldwell Jones and a 1983 first-round pick to the Rockets for Malone in September of 1982. Malone teamed up with Julius Erving, Mo Cheeks, and Bobby Jones to finally deliver a title, ending a three-year streak of conference finals appearances without a championship.

The Worst Trades in Philly Sports History

Three of the worst trades in Philly sports history were made by the same team: the Phillies. These deals proved to be monumental mistakes, hindering the franchise’s progress for years.

Curt Flood to the Philadelphia Phillies (1966)

Curt Flood appeared in only eight games for the Phillies before being traded for pitchers Bob Buhl and Larry Jackson. This proved to be a significant error, as Flood went on to have six consecutive 20-win seasons, winning a Cy Young Award and earning three All-Star selections. He pitched for 17 years after leaving Philadelphia and was inducted into the Hall of Fame in 1991.

Iván De Jesús to the Chicago Cubs (1982)

The Cubs coveted Larry Bowa, but Phillies General Manager Dallas Green, formerly the Phillies’ head of player development, insisted on Ryne Sandberg being included in the deal for Iván De Jesús. Sandberg became a superstar, earning 10 consecutive All-Star selections, nine Gold Gloves, seven Silver Sluggers, and a Hall of Fame induction. De Jesús, meanwhile, posted a modest 2.9 WAR in his three seasons with the Phillies.

Wilt Chamberlain to the Los Angeles Lakers (1968)

Despite being part of one of the best trades in Philly history, trading Wilt Chamberlain to the Lakers in 1968 also lands on this list. The Sixers traded the reigning MVP to the Lakers for Jerry Chambers, Archie Clark, and Darrall Imhoff, and Chamberlain helped Los Angeles win a title in 1972.

Scott Schilling to the Arizona Diamondbacks (2000)

Despite his value, the rebuilding Phillies traded Schilling in his prime for Travis Lee, Omar Daal, Vicente Padilla, and Nelson Figueroa. These players combined for just 9.1 WAR during their time with the Phillies, while Schilling went on to win three World Series titles – with the Diamondbacks and Red Sox – and earn three All-Star selections.

Sonny Jurgensen to the Washington Redskins (1964)

Sonny Jurgensen was a key player traded away, alongside Dick Allen, Moses Malone, Scott Rolen, and Andrew Bynum. While recent trades may not have fully revealed their impact, these deals highlight the risks and potential consequences of the trade market.