Philadelphia Phillies: The 10 worst trades in franchise history

If any organization is around long enough, they are going to make some trades that look terrible after the fact  and the Philadelphia Phillies are no exception. To be clear, there have been some absolutely amazing deals along the way as well with Steve Carlton, Roy Halladay, Curt Schilling (more on him in a bit), and Lenny Dykstra come to mind.

It does make us wonder which trades have risen to the summit of Mount Dumpster Fire when it comes to trades and that can be a bit tricky especially when you look at trades from the last few years. Some of them may look fine right now, but five years from now some low level prospect that got thrown into a trade turns into an absolute stud. As a result, for these rankings we are going to most eschew the more recent moves and leave the hyperbole about most very modern moves to lowly comment section trolls.

The worst trades in Phillies franchise history

There is no science to these rankings, either. They aren’t ranked by WAR gained/lost or anything like that. Especially with earlier trades, comparing moves over the decades is like comparing apples to oranges as we don’t have the same level of info about players that we do now. In the end, these are all educated guesses. Yes, there are going to be differences of opinion on where trades should rank and there are going to be moves that some think should be on the list. In the end, this is a thought exercise and not definitive in any way, shape, or form. 

Enough of the disclaimers that won’t stop people from getting mad online anyways, here are 10 of the worst trades in Phillies franchise history.

Phillies Trade Cliff Lee to the Mariners

The Phillies were the beneficiaries of a very favorable trade that landed Cliff Lee in the first place, but unfortunately they were on the wrong end of the return when they decided to move him back in 2010. Philadelphia sent Lee to the Seattle Mariners for Philippe Aumont, JC Ramirez, and Tyson Gilles.

When you are trading away one of the better pitchers in the entire league, you would prefer to look back and remember the contributions of those they got for him. Well, you can’t in this case. This trade should honestly probably rank higher except that Lee hit free agency after the 2010 season, he came right back to Philly and played for four more seasons.

Phillies Trade for Freddy Garcia

This is a weird one and also a lesson that trades for pitchers have a much higher risk for being duds. Back in 2007, the Phillies were looking to solidify their rotation with a high impact arm and Freddy Garcia had a lengthy track record with the Mariners and White Sox of eating tons of innings and pitching well. So, the Phillies sent Gavin Floyd and Gio Gonzalez to Chicago to nab Garcia.

In hindsight, Philadelphia probably should have noticed that all of those innings had put a lot of mileage on Freddy’s arm and shoulder troubles ultimately cut his time with the Phillies short. He did manage to play in the big leagues for six more seasons with various different teams. Philadelphia would have been better off just keeping Gio Gonzalez who would go on to have a 13 year career in the big leagues including a stretch from 2010-2017 where he was one of the more consistent pitchers in baseball and where he posted a 3.41 ERA primarily with the Nationals.

Phillies Trade Scott Rolen

This is another tough one because the Phillies had their hands forced when Rolen demanded a trade from the struggling Phillies despite them offering him a pretty significant contract. However, Rolen’s mind was made up and the package that Philly ultimately settled on was one that sent him along with Doug Nickle to the Cardinals for Placido Polanco, Bud Smith, and Mike Timlin.

Smith was supposed to be the centerpiece of the trade, but was a bust for the Phillies as a prospect. Polanco was a pleasant surprise and had two different productive stints in Philadelphia. Unfortunately for Philly, Rolen would play in four All-Star games with St. Louis and would be rewarded for an awesome 17 year career where he was a consistent hitter and amazing defender by finally getting elected to the Hall of Fame this year.

Phillies Trade Curt Schilling

Again, another situation where the player wanted out because he wanted to play for a contending team which didn’t exactly help the Phillies in the leverage department. Curt Schilling was a very good pitcher with the Phillies for north of a decade and was coming off three straight All-Star appearances before the Phillies traded him to the Diamondbacks for Travis Lee, Vicente Padilla, Omar Daal, and Nelson Figueroa back in 2000.

Most deals for a guy that has a borderline Hall of Fame resume are going to look particularly great, but the return for Philly was pretty brutal in this one. Padilla was the highlight and he was decidedly medium during his time in Philadelphia. Daal, Lee, and Figueroa were all out of Philly a couple seasons later. As for Schilling, he would become a perennial Cy Young contender and All-Star with Arizona and Boston after he left Philly before becoming one of the more polarizing figures in baseball during his post-playing career.

Phillies Trade Cole Hamels

This was a pretty brutal trade deadline deal looking back. Hamels was a mainstay in the Phillies’ rotation as a borderline ace and a consistent source of innings throughout his nine plus seasons in Philadelphia. However, the Rangers were very aggressive in trying to upgrade their rotation and Philly ended up agreeing to send Hamels and Jake Diekman to Texas for Matt Harrison, Jorge Alfaro, Jake Thompson, Alec Asher, and Jerad Eickhoff.

Jorge Alfaro had his moments, but the rest of the return for Hamels did not do much of anything for the Phillies. Hamels would pitch reasonably well for the Rangers before having a career renaissance with the Cubs. Health issues have kept him out the last few years, but that doesn’t excuse the total lack of a return despite the size of the trade package the Phillies got for one of the best pitchers in the league.

Phillies Trade Grover Cleveland Alexander

To be clear, evaluating any trade from 1917 is pretty suspect because baseball was the Wild West back then with teams having to do some pretty weird stuff to just stay afloat. No one thought that Grover Cleveland Alexander wasn’t one of better pitchers in baseball, but the owner needed money and there was a real chance that Alexander would have to go fight in World War I which carried a unique set of risks. So, Philadelphia traded him to the Cubs for Mike Prendergrast, Pickles Dillhoefer (what a name), and $60,000.

$60,000 was not a small amount of money back then, but Prendergrast and Pickles didn’t amount to much of anything in Philadelphia. Alexander, meanwhile, would go on to pitch 13 more seasons and end his career with a 2.56 ERA and almost 2200 strikeouts. In the third year of the existence of the Hall of Fame, Alexander would be inducted into Cooperstown and is widely considered to be one of the absolute best pitchers to ever play the game. If only Philly had kept him….sigh.

Phillies Trade Ryne Sandberg

The top two worst trades on our list are pretty interchangeable and we won’t fault you if you flip them because it is legitimately pretty close. In 1982, Larry Bowa (a familiar face) was getting older and when the two sides couldn’t agree on a path forward, the Cubs swooped in with a trade proposal that had them send Ivan DeJesus, who could replace Bowa at short for Philly, for Bowa and some young infielder named Ryne Sandberg.

Yeah, THAT Ryne Sandberg. Philly didn’t think much of Sandberg back in those days, but the Cubs saw potential in him and they were very, very correct. DeJesus was not the long-term answer at short that Philly was hoping for as he played just three meh to bad seasons while the Cubs got a future MVP, multi-time All-Star, multi-time Gold Glover, and, of course, Hall of Famer. Again, if you have this as the worst trade in franchise history, we won’t argue.

Phillies Trade Fergie Jenkins

At number one on our list is a classic example of a failure in player evaluation of epic proportions. Fergie Jenkins was a seldom used bullpen arm in Philadelphia and was included in a package sent along with John Hernstein and Adolfo Phillips to the Cubs for Larry Jackson and Bob Buhl. No, it didn’t escape our notice that the Cubs are responsible for the three worst trades in franchise history and yes, it definitely tilted us.

Once the Cubs got ahold of Jenkins, they would convert him into a starter and he would put together a seven year run in the late 1960’s and early 1970’s where he would win 141 games and post a 3.11 ERA and 44.9 rWAR while winning the Cy Young in 1971. He would pitch until 1983 where he returned to play the final two years of his career in Chicago. It took longer than it should have, but Jenkins was eventually inducted into the Hall of Fame in 1991 having pitched 4500.2 in the big leagues as one of the best to ever do it.

As for Philly’s return in the deal, Jackson put together a few decent seasons in Philadelphia while Buhl didn’t do much of anything before retiring a couple of years later.

More Phillies news from That Ball's Outta Here