Philly Front Office

Well, if I did the best trades in Phillies history, you had to assume the worst trades were coming next. The list doesn’t disappoint. All your favorites are here and perhaps some that don’t eat at you daily as much as they should (Freddy Garcia). Instead of ranking them (because I would absolutely put Freddy Garcia #1), let’s go with a chronological approach that also shows that the Cubs were just using us as a talent breeding ground for 65 years…

Best Trades in Phillies History

December 11, 1917 – Grover Cleveland Alexander to the Cubs for Pickles Dillhoefer, Mike Prendergast and $55,000

You are going to notice that the Phillies have made a lot of bad trades with the Cubs over the years. Had an equivalent Cy Young Award been given out before its introduction in 1956, there’s a good chance GCA would have had a few. From 1914-1917, he only led the league in WAR, Wins, Innings Pitched, and Strikeouts each and every season (plus ERA 3 out of 4). What did the Phillies do to reward him? Well, they certainly didn’t pay him! Instead, they sent him to Chicago where he would put up several more peak level seasons and play for 9 more years. Though they have great names (Pickles!!!), the guys they got in return would only play a total of 3 uninspiring seasons collectively in Philadelphia before moving on. The Phillies were an above .500 organization before the move but spent the next 30 years building their nest egg to become the losingest franchise in sports history. A long organizational streak of cheapness and futility was born with this trade.

November 21, 1933 – Chuck Klein to the Cubs for Harvey Hendrick, Ted Kleinhans, Mark Koenig, and $65k

He wasn’t the first and wouldn’t be the last future Hall of Famer the Phillies would send to Chicago. This one wasn’t nearly as bad because Klein didn’t perform up to previous standards after the trade, but that ignores that the pull hitting Klein was a glove fit for the Phillies’ Baker Bowl and the team traded him after an 8 WAR season that saw him finish runner up for MVP. While the players received in return were horrible, the $65k did help the team stave off bankruptcy (see below).

November 21, 1933: Phillies trade Chuck Klein to Cubs

April 21, 1966 – Ferguson Jenkins to the Cubs for Bob Buhl and Larry Jackson

I’m not sure why Fergie Jenkins to the Cubs doesn’t get as much hype as Sandberg to the Cubs in sad Phillies lore. The man only finished with five Top-3 Cy Young seasons including winning in 1971 with an insane 10.1 WAR. While Buhl and Jackson were good Major Leaguers, they were 37 and 35 when the trade happened. Jenkins was just 22. He was elected to the Hall of Fame in 1991. Just a total disaster for a team that was just starting to be good again too. Imagine having Jenkins and Steve Carlton on the same team just 6 years later?

January 27, 1982 – Ryne Sandberg (and Larry Bowa) to the Cubs for Ivan de Jesus

The late, great Ryne Sandberg will be forever known as both one of the best Cubs of all time and the worst trade in Phillies history. It’s one thing for a player to blossom after a trade occurs making the original team look foolish, but it’s another for the team to trade away a good prospect for seemingly no reason. The Phillies did the latter. I wrote all about it…

January 27, 1982: Phillies Trade Ryne Sandberg to the Cubs

December 9, 1982 – Manny Trillo, Julio Franco, George Vukovich, Jerry Willard, and Jay Baller to Cleveland for Von Hayes

The Von Hayes 541 trade has been maligned since it happened. At the time, it was mostly for his first terrible season and the quantity of the deal, how could one guy be worth 5? In the years since though, it was the inclusion of just one name, Julio Franco. Just like Jenkins and Sandberg before him, the Phillies simply had the shortest view in the room and gave up on a prospect they didn’t realize they needed. Would they have held on to Franco for his entire 23-year career? Of course not, but over the next eleven seasons Franco would finish 2nd for ROY, take home 5 Silver Sluggers, 3 All-Star appearances and receive MVP votes 3 times. What were Phillies middle infielders doing during that time? While Juan Samuel was doing just fine at 2nd, Ivan de Jesus and Steve Jeltz weren’t exactly All-Stars at short. For his part, Hayes was pretty good in a Phillies uniform including a great 1986 that had him finish 8th in MVP voting. Probably the best trade on this worst trade list despite its infamy.

July 26, 2000 – Curt Schilling to the Diamondbacks for Omar Daal, Nelson Figueroa, Travis Lee, and Vicente Padilla

Curt Schilling’s trade to the Phillies is considered one of the best Phillies trades of all time. Leaving the team? Not so much. While going to Arizona certainly jump started the Schilling baseball legend (before he ruined it by publicly giving his opinions), it did nothing for the early 2000s Phillies who were dying for any kind of talent infusion. They didn’t get it. Padilla¹ was the best of the bunch, but none became any better than role players in Philadelphia. Meanwhile, Schilling was the story of baseball for much of the next 8 years, winning 3 WS titles in historic fashion. The only reason he isn’t a Hall of Famer is because he’s a giant a-hole.

July 29, 2002 – Scott Rolen to the Cardinals for Placido Polanco, Bud Smith, and Mike Timlin

The relationship between the Phillies and Scott Rolen was famously dysfunctional with the player being right while being a dick about it. I get that he had to go at the time (not that I am defending it), but the return was terrible. Polanco was way better than expected, but Timlin was a rental and injuries had already derailed the once promising Smith at this point.² The Phillies traded the best 3rd baseman of his generation for Polanco and essentially nothing else. No prospects, no lottery tickets, just Polanco. It’s even worse when you realize Rolen just wanted the Phillies to spend money to build a good team.

July 30, 2006 – Bobby Abreu and Cory Lidle to the Yankees for CJ Henry, Jesus Sanchez, Carlos Monasterios, and Matt Smith

In some ways, trading Abreu was the best thing that happened to the Phillies. After the trade, the team went 36-22 and barely missed the playoffs. The team took off the next year for maybe the best run in franchise history. However, that doesn’t negate just how good Abreu was. Even though he was 32 at the time of the trade, he still had an .860 OPS and was good for over 100 walks per season. The Phillies gave him and Lidle (a competent starting pitcher who tragically died in a plane crash at the end of the season) away to the Yankees for nothing. CJ Henry was a former first round pick who had already lost his shine at this point and never made the majors. Hell, he never made it passed A ball. The other 3 combined for 12 innings with the Phillies. An abysmal return for an on-base machine that was terrible at the time and simply confirmed by history.

December 6, 2006 – Gio Gonzalez and Gavin Floyd to the White Sox for Freddy Garcia

There are few players I hate more than Freddy Garcia, but in reality I hate everyone involved in this trade. I hate Garcia for being so terrible and taking the Phillies money. I hate Pat Gillick for NEVER MAKING GARCIA GO THROUGH A PHYSICAL to discover that he was damaged goods. I hate White Sox GM Ken Williams for making the trade knowing that Garcia was injured. Just awful. Gio Gonzalez was a steal from the Jim Thome trade to Chicago and then they got him back in this fleecing. He would become a 2 time All-Star and Cy Young candidate. Floyd needed to get out of Philly, I understand that, but he ended up being a solid #3 starter in Chicago for years. Garcia would pitch just the one season in Philadelphia, making just 11 starts with a 5.90 ERA. Somehow the Phillies would be good in spite of him, but this one was horrific.

December 6th, 2006: I’m Still Mad About Freddy Garcia

December 16, 2009 – Cliff Lee to the Mariners for Tyson Gillies, Phillippe Aumont, and JC Ramirez

This just makes me sad. Of all the trades on this list, for me this was the most unnecessary. After taking them to the World Series, the Phillies traded Lee to make room for Roy Halladay. The thing was that Lee was only making $9m in the final year of his contract. THEY COULD HAVE HAD BOTH!!!!!!!!!!!³ Lee ended up changing teams again and brought the Rangers to the World Series in 2010. Between the 3 prospects, they combined for -1.5 WAR, 2 Canadian citizenships, and 4 good ears. There never was and never will be a way to defend this.

July 31, 2015 – Cole Hamels to the Rangers for Jorge Alfaro, Alec Asher, Jerad Eickhoff, Matt Harrison, Jake Thompson, and Nick Williams

Here’s the thing, this should have been a great trade. Alfaro, Thompson, and Williams were all top prospects coming from a loaded Rangers system. They had something like 7 guys making various Top 100 lists. Every single one of them failed (depending on how you feel about Joey Gallo). All the Phillies got from trading their best home-grown pitcher in my lifetime was 1.5 good seasons out of Jerad Eikhoff. Brutal. The Phillies dynasty didn’t end because they traded away their young talent, it ended because when they traded away their MLB talent, no one panned out.

August 21 to August 31, 2020 – Phillies trade for David Hale, Heath Hembree, Brandon Workman, and David Phelps

It’s impossible not to lump all three of these trades together. During the Covid shortened 2020 season, the Phillies had a great offense, but the bullpen always found a way to give games away. Well, by God the Phillies were going to do something about it! Things could not have gone worse. At least, other than Nick Pivetta, the Phillies didn’t give up much for this quartet.

Hale was the most competent of the bunch with a 4.09 ERA in 11 innings. The stats on the other guys though are a sight to behold. Brandon Workman is the one we all remember. While his ERA was only 6.92, he was an on base machine with an astonishing 2.46 WHIP that season in his 13 innings. This was good for a -.3 WHIP. Hembree had a 12.54 ERA in his 9 innings amassing a sterling -.6 WAR. How did he do it? SEVEN HOME RUNS!!! How is that possible??? The Pièce de Résistance though was Phelps. How can anyone top the last two? Despite being the best of the bunch coming in, Phelps managed a 12.91 ERA in just 7.2 innings, amassing a -.6 WAR. He gave up 5 HRs and at one point gave up runs in 5 consecutive appearances. The worst part was that all 3 of these guys were good before they came to Philly. Phelps had a 2.77 ERA in Milwaukee, Workman had a rough ERA but a 2.92 FIP in Boston, and Hembree had a 1.86 ERA with Boston before he gave up 4 runs with no outs in his last appearance (ironically against the Phillies). Even though we didn’t lose anything but our sanity with these trades, it was the worst possible outcome on the field.

Stats: Baseball Reference

Photo Al Bello/Getty Images

1. This might be lost to history now, but Vicente Padilla was one of the worst watches possible. He was slow, irritated, and certain to let a good pitching performance get completely forgotten thanks to him losing his focus. Win or lose, it was better to simply not tune in to a Padilla start. ↩︎
2. Smith through a 4-walk no-hitter as a rookie where he threw 134 pitches. It is widely believed that the Cardinals blew the kid’s arm out with a heavy workload in the minors then finished him off with that no-hitter ↩︎
3. There are not enough exclamations in the world ↩︎