The best and worst trades in Philly sports history

Miss on a top draft pick? You may get another chance before long. Sign a free agent for way too much money? He’ll come off your books eventually. But come away on the wrong end of a trade, and you could set your franchise back decades — and in the worst cases, cost your team a chance at a title or watch a future Hall of Famer walk out your doors.

Those are the stakes when playing the trade market. And while any decision to add or subtract players comes with a certain degree of risk, the delta between success and failure when making a trade is greater than almost any other area of roster development by nature of the number of players involved and the potential for evaluational missteps.

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And in Philly, we’re no strangers to seeing our teams land on both sides of fence over the years. In fact, some in this city’s history are so monumental that it’s hard to envision them ever being knocked off Philly’s Mount Rushmore of trades, for better or worse.

As we look back at one of the best trades a Philly team has ever made — the Phillies’ acquisition of Steve Carlton 50 years ago — let’s examine the current Mount Rushmore of Philly sports trades, followed by a look at the flip side of that coin.

Remember when we said that making the wrong trade can completely derail your franchise and cost you a chance at a title? Well, it works both ways, and the one thing all these trades have in common is that they ultimately led to Philly winning a championship. If they seem a bit old, that’s because the city only has two titles in the 40 years since the Sixers won in 1983, and neither of those teams were pushed over the top by one big trade — Nick Foles signed as a free agent and most of the Phillies’ best players in 2008 were homegrown talent.

But these four players, all acquired via trade and listed here in chronological order of when they were acquired, proved to be the missing piece needed to put Philly over the top:

Wilt Chamberlain (1965): He’s arguably the best player in basketball history. That alone should put him on this list. That the Sixers only gave up Connie Dierking, Paul Neumann, Lee Shaffer and cash to bring Chamberlain home to Philly — after the Warriors, who drafted him, left the city and moved to San Francisco years earlier — is just the icing on the cake. But the real win here, again, is that Wilt led the Sixers to a title in 1967 alongside Hal Greer and Billy Cunningham as part of what some still consider the best team in NBA history.

Steve Carlton (1972): The Phillies acquired Carlton from the Cardinals in 1972 for Rick Wise and altered the course of the organization. They were a struggling club that hadn’t won a pennant in over two decades and failed to finish over .500 for several years. They didn’t do that in Lefty’s first two seasons with the club, despite Carlton putting up some incredible numbers that first season. But by the mid-’70s, the Phillies were a winning team, and by 1980, they were world champions for the first time in their nearly 100-year history.

» READ MORE: The summer of Super Steve still sticks to the soul of this fan who saw greatness up close

Bernie Parent (1973): When Parent left the Flyers in 1971 as part of the trade that brought Rick MacLeish to Philly, the Canadian was a pretty good goaltender. When he returned from Toronto in 1973, he was one of the best in the game. The Flyers gave up goalie Doug Favell and a first-round pick to the Maple Leafs for Parent and a second-rounder. Parent’s impact was immediately felt as the Flyers won back-to-back titles the next two seasons behind stellar goaltending from one of the franchise’s most beloved players.

Moses Malone (1982): Not unlike the trade that brought Wilt to Philly, the deal for Malone helped give the Sixers the missing piece they needed to put them over the hump and deliver a title. 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 snap a three-year streak of the Sixers making it to at least the conference finals only to fall short of a championship. But with their new addition, the team delivered what would wind up being the most recent title for the Sixers, who have only been back to the NBA Finals once since. Malone also could’ve easily found himself on the list of worst trades, as the team dealt him away in 1986, but since that trade was just one of many on that June day in ‘86 that altered the course of the franchise, he’ll only appear once here.

Honorable mentions: Norm Van Brocklin (1958), Jim Bunning (1963), Ron Jaworski (1977), Eric Lindros (1992), Curt Schilling (1992), Terrell Owens (2004), Roy Halladay (2009), Cliff Lee (2009), Jason Peters (2009)

It might not surprise you that three of the worst trades in the history of Philly sports were made by the same team — the losingest team in sports history and the one that has been around in this city for by far the longest — the Phillies.

Here’s a look at the Mount Rushmore of terrible Philly trades, as well as a few honorable mentions.

Ferguson Jenkins (1966): Jenkins appeared in just eight games for the Phillies prior to their decision to trade him (along with John Herrnstein and Adolfo Phillips) early in the 1966 season for a pair of pitchers, Bob Buhl and Larry Jackson, who didn’t do much during their time in Philly. The decision to part ways with Jenkins proved to be a massive mistake, as he started a run of six consecutive 20-win seasons in which he won a Cy Young Award and was named an All-Star three times. Jenkins went on to pitch for a full 17 years after the Phillies traded him, and was inducted into the Hall of Fame in 1991. This won’t be the last time the Phillies wind up on the wrong end of a trade with the Cubs.

Ryne Sandberg (1982): The Cubs really wanted Larry Bowa, but their general manager at the time was Dallas Green, the Phillies’ former head of player development. And he knew of a guy in their farm system named Ryne Sandberg that he demanded be included in the deal for Iván De Jesús. As it turns out, it was that young prospect who turned out to be the best of the group. Sandberg went to 10 straight All-Star games from 1984 to ‘93, won nine Gold Gloves and seven Silver Sluggers, was the NL MVP in 1984 and earned a Hall of Fame induction in 2005. Meanwhile, De Jesús posted a 2.9 WAR total in his three seasons in Philly; Sandberg, on the other hand, reached that number in all but three of his 15 seasons as a Cub.

Chamberlain (1968): As previously mentioned, the Sixers trading away Malone in 1986 was a strong contender here, as was the deal that sent Charles Barkley to Phoenix in 1992. But for various reasons, like Barkley demanding that trade and forcing the Sixers’ hand and Moses’ deal being one of several that day, we’re going to give the nod to Wilt, who was also part of one of the best trades in city history. That’s just the way things work when you play the trade game. Wilt was on the wrong side of 30 when the Sixers traded him to the Lakers for Jerry Chambers, Archie Clark and Darrall Imhoff, but he was the reigning MVP and was still good enough to help Los Angeles win the title in 1972.

Curt Schilling (2000): Say what you will about Schilling, but the dude could pitch. So that’s what made it so odd when the rebuilding Phillies traded away the righty in the prime of his career for Travis Lee, Omar Daal, Vicente Padilla, and Nelson Figueroa, a quartet of players who combined for just 9.1 WAR in their time with the Phillies. Schilling, however, went on to win a trio of World Series titles — first with the Diamondbacks in 2001, and then twice with the Red Sox (in 2004 and 2007) — was named to three All-Star teams and won more than half of his 216 career victories after leaving Philadelphia.

Honorable mentions: Sonny Jurgensen (1964), Dick Allen (1969), Malone (1986), Barkley (1992), Scott Rolen (2002), Andrew Bynum (2012)

Are we light on recent trades on this list? Sure, but there’s a good chance that the full weight of the trades made in recent years won’t be felt for some time — and by then we may have to carve a new face on our Mount Rushmore.