Worst Trades in Phillies History

Posted by Johnny Goodtimes, Mon, July 29, 2013 09:52 AM | Comments: 33

This article was written by our friend Johnny Goodtimes, author of Philly Sports History.

Ryne Sandberg

In the Hall of Fame with a Cubs hat.

With the trade deadline approaching, and as we all wait to see what Ruben is going to do, I thought we’d take a look back through the years at some trades that didn’t work out so well for the Phillies. Incredibly, this team has such a knack for terrible trades that 5-for-1 (Von Hayes was much better than Phillie fans give him credit for) and the Scott Rolen debacle (they got a young Placido Polanco and a solid Mike Timlin in return) don’t even crack the top 5.

#5. Freddy Garcia for Gio Gonzalez and Gavin Floyd. The Phils were looking for a front end of the rotation guy, and Pat Gillick apparently looked at Garcia’s 17 wins in 2006 more closely than he did his 4.53 ERA. He also must not have looked too closely at his right shoulder…after a 1-5 start, Garcia was finished. He made $10 million to earn one more win than I did in 2007.

#4. Grover Cleveland Alexander and Bill Killifer for Pickles Dillhoefer and Mike Prendegrast. Phillies ownership was, as usual, experiencing cash flow problems after the 1917 season. And so they let arguably the greatest pitcher in team history go for a catcher who batted .091 for his new squad and a pitcher who would be done in a year. Grover Cleveland would win another 183 games after leaving the Phillies.

#3. Curt Schilling for Travis Lee, Vicente Padilla, Omar Daal, and Nelson Figueroa. Listen, we all agree with Ed Wade that Schilling was a horse’s ass. Nonetheless, you would have thought a pitcher of his caliber would have brought more in return than the four mediocre journeymen they got. Not Ed Wade’s finest moment.

#2. Ferguson Jenkins for Larry Jackson and Bob Buhl. The Phillies were trying to recapture the magic that took them to the brink of the Series in 1964, and decided to trade a young reliever named Ferguson Jenkins for two wily old veterans. The key word was old. Jackson was actually serviceable as a starter, while Buhl was out of the league in a year. Jenkins went on to a Hall of Fame career, winning 284 career games. Sadly, only two of those wins came for the Phillies before they gave him away.

#1. Larry Bowa and Ryne Sandberg for Ivan DeJesus and Bill Caudill. It’s worth noting that Sandberg was the throw-in on this deal. The Phils tried to give the Cubs Bowa and Luis Aguayo. The Cubs said no, but they’d take Bowa and Sandberg. The Phils caved. The Cubs got a superstar Hall of Famer. The Phils were stuck with Aguayo, who turned out to be serviceable at best, and DeJesus, who was a good glove, played shortstop for the team for 3 years.

Those are the worst 5 trades the Phillies have ever made, but what about the worst trade the Phillies DIDN’T make? Hard to say, and there are probably plenty of them that never saw the light of day. But we do know about one, thanks to Krukker. He told Sam Donnellon a couple of years ago that the Phils were talking to the Mariners in ’93 about trading for Randy Johnson. But the Phils didn’t want to part with Mike Lieberthal, so the trade never happened.

What was the worst trade in Phillies History

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About Johnny Goodtimes

Johnny Goodtimes has written 17 articles on Phillies Nation.

Johnny Goodtimes is not only Philly's premiere quizmaster, he's also a Philly sports history junkie, starting his own site, Philly Sports History. He has written humor and sports columns for the City Paper, Philly Mag, and the Metro, and still harbors an unhealthy resentment towards Rod Barajas.

  • Posts: 804 schmenkman

    Avatar of schmenkman

    Aside on the Sandberg card — was this format used in any year other than Topps 1974 (4 years before he was drafted, and was 14-15 years old)?

  • Posts: 0 Johnny Goodtimes

    Hey Ryan, like I said above, that was not as bad of a trade as many Phillies fans seem to make it out to be. In fact, you would have a hard time saying that the Indians made out better than the Phillies on the deal. Von Hayes was actually pretty good, and Three of the Five in that trade were career journeymen who did essentially nothing for the Indians. Manny Trillo was still pretty good, but only played one year in Cleveland. Obviously, Julio Franco was the star of the bunch, but if you look at the numbers of his 6 years in Cleveland, they are very similar to Hayes’s next 6 years in Philly. Franco was a better hitter for average, both were good base stealers, and Hayes had a higher OPS. The Indians may gotten had a slight advantage in this trade, but nothing anywhere near what the Cubs got when we gift wrapped them Ryne Sandberg.

  • Posts: 0 Johnny Goodtimes

    Another trade worth revisiting in a few years: Hunter Pence for Cosart and Singleton. Cosart has been lights out thus far (small sample size, of course, but wow), and Singleton is considered a “Can’t Miss”. This deal could very well turn out to be one of the worst in Phillies history.

  • Posts: 0 George

    When a player asks strongly to be trade, as Schiiling did, it limits what you can get for him.
    I think there were worse trades made than that one. I’m with Mr. Goodtimes in thinking that the Pence deal will wind up one of the worst, and the Lee to the Mariners so far has been a complete mess and may wind up at least as number 6.

  • Posts: 0 bob fisher

    the worse trade was the one they didn’t make-getting rid of howard when he was worth something!!!!!!!

  • Posts: 0 Ryne Duren

    I voted for the Fergi Jenkins trade. He won 20+ games 6 straight years for the Cubs. And the Phils thought he wouldn’t be any good since all he threw were fastballs! It seems that back then they couldn’t evaluate talent either.
    As far as the Sandberg trade. Most people point to that, but if you look at his minor league state. and his first 2 years in the show he wasn’t that outstanding. That plus the Phils did make it to the world series with Dejesus. Though I didn’t think he was that good. It’s one of those trades that you never know. Sandberg turned out to be a hall of famer. I can’t fault them for that. I just wish we’d be on the other end of that you never know thing. We always get the “you know” this guy stinks. But Jenkins for two old pitchers nah. I do understand the fact that the Phillies were trying to be contenders that year and were looking for an established pitcher or two for the rotation. They weren’t willing to let Jenkins just pitch. If they did they might have realized they had a good one. Jenkins suffered from the same thing Buddy ryan did with that wide receiver. I can’t recall his name offhand, but Buddy said all he can do is catch touchdowns. All Jenkins did was throw fastballs. Go figure!

  • Posts: 0 Jimmy

    No doubt in my mind its Curt, Travis Lee was a disaster at first, and besides one good half none of the pictures ever amounted to much. worst of all After the trade Curt won Three World Series, Two of which came after the Phillies were starting to be competitive. Which means he really could have helped if they kept him.

  • Posts: 84 Tom

    Avatar of Tom

    Has to be the Sandberg trade! Mainly because he was a throw in and that the Phils weren’t able to recognize that, aside from his offensive abilities, Sandberg, who came up as a 3rd baseman, had the ability to be a Gold Glove 2nd baseman as well!!

    • Posts: 0 john

      lee thomas knew, why didn’t they. he was playing third at the time, and blocked by schmidt !

  • Posts: 0 Eddie J

    At least in the Sandberg trade the Phils got a serviceable starting shortstop for a few years. The Garcia trade may end up being worse, depending on how the careers of Floyd and Gonzalez (and BioGenesis) shake out. Floyd was a decent 3-4 until he blew out his elbow but Gonzalez may be a 1-2 for a lot of years (unless the juice put him there).

  • Posts: 0 billkirk

    Ok, these were some pretty bad trades. But how about Ruben “what am I doing here, how in the world did I get this job??” Amaro giving Cliff Lee away for a bucket of baseballs in the 2009 offseason? And if you’re talking trades, you should include signings too. Another three RAJ gems are Ibanez in 2008 (3/36) when market said one year, $5 million like Bobby Abreu, Ryan Howard extension when he was already in decline and his free agent year had a glut of all star 1B, and paying Mariano Rivera money to Papelbon for half the performance and none of the class.

    • Posts: 804 schmenkman

      Avatar of schmenkman

      No argument on the extension, but Ryan Howard was already in decline in April 2010? And to be fair, Lee was traded for a bucket of balls in each one of his trades, including the one to the Phillies.

      • Posts: 4388 Lefty

        Avatar of Lefty

        I find it amazing that the three Lee trades (Cle-Phi, Phi-Sea, Sea-Tex) have netted nothing as far as Major Leaguers thus far. The Jury is obviously still out on some, especially the four guys Seattle got from Texas (Smoak still might be good) , but so far- meh.

        Sounds like a good reason not to trade him to me.

      • Posts: 2952 Chuck A.

        Avatar of Chuck A.

        The only good reason TO trade him is if they get a serious haul in return. I’m all for moving him as he’s their best trade chip…but only if it makes sense.

      • Posts: 804 schmenkman

        Avatar of schmenkman

        @billkirk, why focus on the 2009 WS, and ignore the .375 avg (.951 OPS) in the NLDS, or the .375 avg (1.457 OPS) in the NLCS that year? Overall in the 2009 postseason he hit .278 with a .968 OPS. Tough to see evidence of decline there.

        And Howard was known as a slow starter even then, and a .757 OPS wouldn’t (or shouldn’t have) raised any red flags:

        April 2007: .786 OPS
        April 2008: .640 OPS

      • Posts: 0 billkirk

        Ok, I concede the numerical decline was just getting started and RAJ can be forgiven for assuming it was just a typical slow start. But how do you justify a deal so far in advance of free agency that is not team friendly, when the player’s walk year contained (at the time) a virtual HOF wing of talent in Pujols, Fielder, Gonzalez, et all. Pujols and Fielder did both hit the market, Howard’s clearly behind those two and would have commanded far less than what the Phillies are paying him. When Howard signed, he was already over 30 and did not profile as the type of player who would age well. He can only play first base in a non-DH league. It made no sense then. It makes less sense now.

      • Posts: 804 schmenkman

        Avatar of schmenkman

        Agreed, and I wouldn’t try to justify the timing. Was only questioning the “already in decline” portion.

  • Posts: 0 Ken Bland

    Perhaps telling is that the subject presented at this time where one easily wonders whatever happened to the “epic” second half is the worst trades in Phillies history. Would the first of what may or may not be 2 parts be the best trades in Phillies history if this were a contending trade deadline? Is there any market at all so supportive that they’d rather read that then the memories of bad deals that went even more awry? Maybe sports fans universally are so cynically labeled that this IS the way to travel. All I know is the Phillies need a half dozen Don Demeter for Senator Bunning deals in about 49 hours, and somewhere between the freeze and the particular GM aren’t likely to produce that. Plus, I wonder whatever happened to Adolfo Phillips, but that may be another story for another time.

  • Posts: 0 Frank

    The double Lee trade. Never should have been traded in the first place, think of the possibilities. We certainly wouldn’t be in the mess were in now.

  • Posts: 0 John

    The Phillies should trade Rollins to the Tigers for a prospect. They should offer Utley for Kemp so that way Dodger could control wether to keep Utley or persue Robinson Cano. Shop out Papelbon and eat some cash. Work on rehabing Howard and work on hitting the outside pitches to opposite field and curve balls. Trade Young and Lee to the Rangers for Profar. Look for free agent relievers next year.

  • Posts: 0 George

    It’s a down season, so I can understand everyone griping about the Phils’ bad trades.

    But what about other teams’ bad trades? It seems to me that there are lots of examples there, too, and it seems like rating the bad trades by the Phils is just more negativity.

    They’ve also made many good trades, even under Amaro, and rather than whining so much, maybe some of THOSE should be rated. Ken pointed out one, the Demeter for Bunning deal, but the initial Lee trade and the Halladay deal have been pretty much glossed over. Personally, I think it would be more relaxing to hear about the best trades, particularly when this season that may be the one positive thing to talk about.

  • Posts: 0 Bart Shart

    QUESTION: Has anyone ever investigated some of the contracts that Ruben Amaro, Jr. has doled out over the years? He just signed a highly questionable one for the services of an unproven Cuban pitcher. The Howard deal was signed with two whole years left on his old contract. I wonder if Ruben gets a some kickback for signing such generous and questionable deals? Or, is he just a really inept general manager struggling with himself and this team’s future. After all, he is a Stanford graduate.

  • Posts: 0 Andrew from Waldorf

    The Braves just won in extra innings. I watched the game.

    I guess I am the only one still monitoring them.

    The phils still play them 13 times so if they went 12-1


    highly unlikely.

    Some of the signings are worse than any of the trades.
    Google Dummy Amaro Jr. and see.

    • Posts: 0 Ryne Duren

      hahahahahahahahaha! Funny ending there Andrew.

    • Posts: 74 loupossehl

      Avatar of loupossehl

      I see “them” going 12-1.

      I just don’t have a good feeling about who is “they”.

  • Posts: 0 Freyday17

    Everyone forgets Jack Sanford for Valmy Thomas and Ruban Gomez !

  • Posts: 0 mark Burt

    Easily the worst trade in Phillies History: Jack Sanford for Ruben Gomez and Valmi Thomas.

  • Posts: 804 schmenkman

    Avatar of schmenkman

    Looking back, PN actually analyzed the “five-for-one” trade, and found that the Phillies actually did ok:

    “On its surface, the Phillies won the 5-for-1 trade by an entire 2009 Ryan Howard, and then some.”


  • Posts: 0 Mc Q

    To Cleveland: 2B Manny Trillo, INF Julio Franco, RHP Jay Baller, RF George Vukovich, C Jerry Willard
    To Philadelphia: OF Von Hayes
    – See more at: http://philliesnation.com/archives/2010/07/big-trades-and-von-hayes/#sthash.G8E6R2Rp.dpuf

  • Posts: 804 schmenkman

    Avatar of schmenkman

    Yep, those are the names. ;-) As that article shows, the Phillies made out pretty well.

  • Posts: 74 loupossehl

    Avatar of loupossehl

    One of my favorites: trading Jack Sanford to the Giants for Ruben Gomez (who stunk) and Valmy Thomas (who disappeared in a year after hitting .200).

  • Posts: 0 Johnny Goodtimes

    “Nonsense”? You seriously don’t think that the Garcia for Floyd/Gio was absolutely terrible? Are you arguing that it was a good trade? I can’t possibly understand how anyone could think that, but I’d love to hear your reasoning.

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