The last few months in the world of Philly sports certainly haven’t been lacking in intrigue.  

The Sixers’ offseason has been dominated by the drama surrounding Ben Simmons following his disappointing performance in the Sixers’ embarrassing playoff defeat against the Atlanta Hawks. It came to a head recently with Simmons formally demanding a trade, even going as far as to threaten to skip training camp if a deal can’t be done by then. 

This marked the second time just this year that a high-profile Philly athlete has requested out, following Carson Wentz’s “desire for a fresh start” (a.k.a. trade request) back in January. While that situation was resolved in March when Wentz was dealt to the Indianapolis Colts, the Simmons situation is still ongoing and will very likely not have a resolution for some time.  

Though it’s far from the first time a Philly athlete has requested to be dealt, they are few and far between. There have been notably untenable situations in this city resulting from contract disputes (Eric Lindros) and just all-around toxicity (Terrell Owens) that ended with breakups. But Philly athletes of Simmons’ and Wentz’s stature requesting out, let alone in the same year, is pretty rare for the most part and will always dominate sports dialogue in the city. 

So, with that being said, let’s take a look back at the other most notable Philly athletes to request a trade and evaluate both the circumstances surrounding them and what the ultimate outcome was.

Wilt Chamberlain

Chamberlain was already bigger than life, literally and figuratively, when the Sixers acquired him from the San Francisco Warriors in 1965. He had, among other things, a 100-point game, an MVP award, six All-Star nods, and five All-NBA nominations under his belt.

Chamberlain’s reign of dominance continued in his three seasons as a Sixer. Playing alongside fellow Sixer great Hal Greer, Chamberlain was an All-Star and named All-NBA each year in Philly, also logging three rebounding titles, a scoring title in 1966, and three-straight MVP awards. It culminated in Chamberlain’s and the Sixers’ first NBA title in 1967. 

Yet in the summer of 1968, following a 62-win season that ended with a conference finals loss to the Boston Celtics, Chamberlain requested a trade. Why exactly he asked out is disputed. Some said that he was mad that Sixers owner Irv Kosloff scrubbed a deal between Chamberlain and previous owner Ike Richman that would’ve awarded Chamberlain a 25% ownership stake after he retired. Others said he simply sought the brighter lights of a higher-profile city like Los Angeles.    

Whatever the reasoning, Chamberlain wanted a fresh start. He reportedly even went so far as to threaten to jump to the ABA if he wasn’t traded to a West Coast team. His request was ultimately granted in July of that year, as he was sent to the Los Angeles Lakers for big man Darrall Imhoff, guard Archie Clark, and forward Jerry Chambers.

In what would become a trend in these sorts of situations, the Sixers very clearly got the short end of the stick in the deal. Though Clark was a productive player, Imhoff was traded after two seasons, Chambers never played a game in Philly, and the Sixers went nearly a decade before they won another playoff series. On the other hand, Chamberlain continued his dominant ways, making two more All-NBA teams, clinching three more rebounding titles, and winning Finals MVP en route to his second NBA title in 1972.         

Charles Barkley

No one doubts Charles Barkley’s status as a Sixer legend. The first-ballot Hall-of-Famer ranks in the top-five in franchise history, among many other categories, in points, rebounds, field goal percentage, and steals. As a Sixer, he led the league in rebounding in 1988, was named All-NBA seven times, and played in six All-Star games, earning MVP honors at the 1991 game. He more than earned the right to have his number hung in the rafters at the Wells Fargo Center.        

But for all of Barkley’s personal achievements in Philly, the team’s success left a lot to be desired. As a young, budding member of the former title-winning Erving-Malone-Cheeks-led Sixers, they consistently came up short in the playoffs, only making the conference finals once in 1985. When the old guard faded away and Barkley became the clear-cut star of the team, he couldn’t overcome Michael Jordan’s Chicago Bulls in 1990 and 1991. And by 1992, he was the lone star of a gutted, mediocre Sixers team that had just missed the playoffs for only the second time in the previous 18 seasons.  

Barkley had also developed a bit of a reputation with his outspoken nature. He was never one to shy away from airing out his frustrations with teammates, Sixers management, and the media. Off-the-court issues, including a 1991 bar fight, weren’t exactly beneficial as well.

With the increasingly-fed up Sixers stuck in neutral and Barkley not wanting to waste his prime years losing, he pushed for a trade. He got one in the summer of 1992, as the Sixers dealt him to the Phoenix Suns for guard Jeff Hornacek and big men Tim Perry and Andrew Lang. 

While all three players acquired by the Sixers were either dealt (Hornacek in 1994 and Perry in 1995) or released (Lang in 1993) over the following three seasons, Barkley thrived in Phoenix. In his first season as a Sun, he won league MVP and took them to the NBA Finals. He would also go on to add five more All-Star nods and four more All-NBA nominations to his resume.  

Curt Schilling

Following uneventful stints with the Baltimore Orioles and Houston Astros, Curt Schilling was dealt to the Phillies early in the 1992 season. It turned out to be one of the greatest trades in team history. Schilling quickly developed into the team’s ace, playing a major role in the team’s surprise run to the 1993 World Series as MVP of the National League Championship Series.

The years following that run saw Schilling continue to blossom into one of the best pitchers in baseball. His 1997 season saw him set a single-season franchise record in strikeouts (319) and finish fourth in NL Cy Young voting and 14th in NL MVP voting. He also made three-straight All-Star appearances from 1997-99, leading the team in wins, ERA, complete games, and shutouts every one of those years. 

But as Schilling ascended to greatness, his team took a nosedive. Following that 1993 season, the Phillies never again came close to even sniffing the playoffs for the rest of Schilling’s tenure, failing to put together a winning season in that time.  

Frustrated with the team’s lack of success, Schilling requested a trade to a contender in the middle of a dismal 2000 Phillies season. He was then dealt at the deadline to the Arizona Diamondbacks for first baseman Travis Lee and pitchers Vicente Padilla, Omar Daal, and Nelson Figueroa. 

While both Lee and Padilla put together a few solid, though uneventful, seasons in Philly, Schilling maintained his dominant ways. He would log three more 20-win seasons, make three more All-Star teams, and finish as the runner-up in Cy Young Award voting in 2001, 2002, and 2004. He went on to win his first World Series title with the Diamondbacks in 2001, of which he was named co-MVP, and clinched two more titles with the Boston Red Sox in 2004 and 2007.    

Scott Rolen

Yet another casualty of that forgettable era of Phillies baseball.  

After debuting in 1996, Scott Rolen developed into one of the league’s premiere third basemen following his 1997 National League Rookie of the Year campaign. During his time in Philadelphia, Rolen earned three Gold Gloves, a Silver Slugger, and made an All-Star team in 2002. He ranks in the top-five in games played, runs scored, batting average, hits, doubles, home runs, and OPS among all third basemen in Phillies history.  

But like Schilling, Rolen had little confidence in management’s ability to build a consistent winner. A feud with manager Larry Bowa also didn’t help matters. So, in 2002, after declining a massive extension in the offseason, Rolen requested out. The Phillies granted his wish at that season’s trade deadline, shipping him to the St. Louis Cardinals in exchange for second baseman Placido Polanco and pitchers Mike Timlin and Bud Smith.

Though Polanco was productive in seven seasons over two stints in Philly, there’s no way to argue the Phillies got the better end of the deal. Rolen went on to play in six more All-Star games, earn four more Gold Gloves, and win a World Series with the Cardinals in 2006 in a career that could very likely get him a plaque in Cooperstown at the Baseball Hall of Fame. 

Allen Iverson

A.I.’s legacy in Philadelphia is everlasting. His decade-long career as a Sixer was highlighted by seven All-Star nods, seven All-NBA nominations, four scoring titles, and an MVP award in 2001. Of course, his MVP campaign memorably culminated in a trip to the NBA Finals. In all, he ranks in the top five in franchise history in points, assists, steals, made threes, and made field goals. There’s a reason why he receives a hero’s welcome every time he returns to the city. 

But the end of Iverson’s first stint in Philly was volatile to say the least. While Iverson stayed productive in the seasons following the Finals run, even winning two scoring titles in 2002 and 2005, the team’s playoff fortunes faltered. They won just one playoff series in the following five seasons and missed the playoffs altogether in two of those years. It didn’t exactly help that Iverson skipped practices, showed up late to games, and feuded with coaches during that span. So, by the winter of 2006, his days in Philly were clearly numbered.   

After the Sixers got off to a 5-12 start to the 2006-07 season, Iverson formally requested a trade. He got his wish in December of that year, getting sent to the Denver Nuggets for guard Andre Miller, big man Joe Smith, and two first-round picks in the 2007 draft.

This may be the one instance where a Philly team can somewhat claim a draw in a trade request scenario. Though it probably put off a much needed rebuild, Miller was a stout lead guard, helping the Sixers get back to the playoffs in 2008 and 2009. In Denver, Iverson was an All-Star in his two seasons as a Nugget and led them to the playoffs both years, but they couldn’t get past the first round. Iverson would make two more stops in Detroit and Memphis before ending his career in Philly in 2010.