13 Worst Cubs Trades since 1960

We've done the best Cubs trades of the past 50 years, now let's do the worst.  In some ways, this list was tougher, not because there weren't enough bad trades but because there were too many.  I could have limited this list to just 11 terrible deals like last time, but that would have meant leaving a few off the list that really irked me at the time.  So I gave up trying to pare down the list and went with an unlucky 13 with one honorable mention.  The Lou Brock deal is often singled out as the Cubs worst trade, but I consider the Lee Smith trade to be even worse.  It's bad enough that they turned down a far better deal involving a future Cy Young pitcher (whom I'll reveal later), but they turned around and accepted a terrible offer from the Red Sox instead.  In the long term view, the Smith deal would also spur a series of unfortunate events that would set the Cubs back for a decade. Two things to note as you read through the captions in the gallery:

1) Note how many times the Oakland A's seem to be involved when it comes to making great players out of Ex-Cubs.

2) Note the love/hate relationship the Cubs have had with relief pitchers.  They oscillated between trading good young players for washed up relievers and trading young, talented relief pitchers for journeymen.  Whether it was love or hate, however, one thing was consistent:  The Cubs always seemed to wind up on the wrong end of the trade.  Perhaps when it came to making trades involving relievers, the Cubs would have been wise to follow the George Costanza formula for success -- Do the complete opposite of your instincts.
 In the interest of brevity, I've left out a couple of throw-ins who didn't make an impact one way or the other, but the principle players are all mentioned in the list.

This list is not for the faint of heart....

Filed under: Cubs Nostalgia

Tags: Cubs, Trades


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  • I remember the Jon Garland trade so well. It was one of those trades you knew right away was horrible, John Garland was already being hyped as the best Cubs pitching prospect and they traded him for a mediocre middle reliever. This trade was slammed by everyone in baseball when it happened.

  • In reply to rodeosteve:

    Apparently the Cubs were the only team that didn't know that Karchner's arm was nothing but a wet noodle that year. The thing is, it could have been worse. Garland was good but some people thought he could have been even better. But maybe the baseball gods showed a little pity on the Cubs and allowed Garland to be good, but not great.

  • In reply to rodeosteve:

    Very true, Garland wound being a okay pitcher , not a great one. Still that was trade , that when it happened ,I was like WTF? I thought it was a joke at first, who trades your best pitching prospect for a so-so middle reliever?

  • In reply to rodeosteve:

    And the sad thing is the Cubs did it twice that year...they also traded Todd Noel (who most thought was even better than Garland) for Felix Heredia. Heredia and Karchner both almost ruined the Cubs playoff chances in '98.

    As for Garland...would have liked to have had him...innings eater who keeps the ball down...seems like he would have been a good fit in Wrigley.

  • In reply to rodeosteve:

    I also think Garland would have been a good fit with the Cubs. Proof positive that Ed Lynch was a moron as the Cubs GM. Only worse GM was Jim Frey who was a laughingstock . The story is that the Cubs CEO than was a dude named Don Grenesko, a pencil pusher sent thee by the Tribune CO. He was a classic case of a empty suit who after being around the Cubs a bit though he knew baseball as much as then GM Dallas Green and started to interfere in baseball matters. That was the main reason Dallas Green quit, he could not stand working with Don Grenesko anymore and his insisting in having a major say so in day to day personal matters. Once Dallas Green quit , Don Grenesko wanted to pick someone who would be more pliable to his wishes, like Jim Frey. Well Jim Frey was a disaster and after Grenesko was pushed aside by the Tribune Co , Frey's days were numbered.

  • In reply to rodeosteve:

    I have this vision of other GMs falling over themselves whenever Jim Frey wanted to talk deal.

    Good story about Gresenko! We've probably all worked for someone like that at some point...can't blame Green for leaving. Green still deserves all the credit for that '89 playoff team. He and/or Goldsberry either drafted or traded for Maddux, Sandberg, Dawson, Grace, Dunston, Walton...just for starters. They made that team. The good thing about 1989 is that Frey still hadn't had enough time to start destroying it with bad trades.

  • In reply to rodeosteve:

    Ken Holtzman for Rick Monday worked out fine. The Cubs were aging, and not going anywhere, and the A's got a horse. The Cubs got a consistent bat and a fan favorite. Monday's saving of an American Flag at Dodger Stadium made him a fan favorite there, and when in the 1976-77 offseason he had a contract dispute with the Cubs, the Cubs shuffled him off to the Dodgers for Bill Buckner and Ivan DeJesus.

    Buckner was very productive as a Cub as was DeJesus, but in 1982, Dallas Green turned DeJesus into Larry Bowa and Ryne Sandberg. In 1984, Buckner was sent to the Red Sox for Dennis Eckersley.

    That's where the cycle ends as Bowa was released, Eckersley was traded for minor leaguers and Sandberg retired. But the Cubs got productive seasons out of Holtzman, Monday, Buckner, DeJesus, Sandberg, Eckersley and even Bowa. So they had to give up a good player.

  • In reply to tjbrown:

    That's a positive way to look at it. You might want to check out my earlier piece on Best Cubs trades -- some of the deals you mentioned are on that list.

    I was actually a big Rick Monday fan, so that deal wasn't as bad as some of the others - but he was a good, but not great player save the 1976 season. He definitely wasn't a difference maker.

    I think when you're going nowhere, it's better to build with young pitching -- yet the Cubs dealt away Holtzman, Jenkins, Gura, and Hooton (a deal that could have also made this list). That would have been a heck of staff to build around along with position players like Billy North, Andre Thornton, Jose Cardenal, and Manny Trillo.

  • In reply to tjbrown:

    I have another real bad Cubs trade, the 1975 trade of Burt Hooton to the Dodgers for Geoff Zahn. Zahn did nothing for the Cubs and only became a good pitcher for the California Angels in the late 70's and early 1980's .Burt Hooton became a better pitcher for Dodgers and became one the games most consistent pitchers throughout the 1970's and into the early/mid 80's

  • In reply to rodeosteve:

    We must be on the same wavelength because I just thought of that one too. I missed it the first time around but that one definitely deserves a mention. Cubs could have had a pretty nice staff if they would have had a nice staff in the late 70s with Hooton, Gura, and Reuschel...

  • In reply to rodeosteve:

    That's pretty funny John, but I was thinking of that one for a while. It was a bad trade from the get go, Hooton won 12 straight with the Dodgers that same year. The Cubs back then were run by morons back then.

  • In reply to rodeosteve:

    The whole Lou Brock was traded and became a HOFer -woe is me thing is getting really old! For one, Brock is probably one of the most overrated players in the Hall. His whole membership is based on the 3 World Series he appeared in. The 3,000 hit were accumulated over time. Brock overall was not a dominant hitter like Pete Rose or even Tony Gwynn. He could one thing good and that was steal bases. He was never an especially great defensive player. As for the trade itself, at the time the Cubs were in a pennant race and needed a starting pitcher. At the time Broglio has just come off a 18 victory season and Brock was doing nothing for the Cubs. All the whiz kids who think they know everything, where were you going to play Brock? Take Billy Williams out? Brock was going nowhere at the time. It seemed like a good trade for the Cubs at the time. Who knew Brock would find himself at that exact moment? The Smith trade was far worse and did hurt the Cubs for long time. Why does Jim Frey get a pass when he took what was a good team with Dallas Green and pretty much dug them into a hole? But John Holland, who did some good things and built the '69 Cubs is looked so down upon. Ill take Holland over Frey as a GM anytime!

    FYI. Cure for cancer that helped me. http://www.aCURE4cancer.com

  • In reply to mikechi59:

    Hey, I agree with you on the Smith deal. It set the Cubs back for an entire decade -- but I very much disagree on the Brock deal. Of course, we have the benefit of hindsight -- and I also know by today's standards and advanced metrics, Brock isn't as good as his legend suggests...but it was still a bad deal.. The Cubs were not yet contending in 1964, they were 76-86. And when Brock left, they stuck Jimmy Stewart and George Altman in LF. They combined to hit .228 with 4 HRs. Even if you think Brock was overrated, he was still much, much better than that combo platter -- even while he was still with the Cubs. And they had plenty of room to play both Brock and Williams (at the time Williams was playing RF).

  • In reply to walrus:

    I do agree, by the way that Jim Frey doesn't get enough grief. But between you, me and Steveo maybe we can get an anti-Jim Frey campaign going!

  • In reply to walrus:

    One thing that aggrivates me even more is that Ken Holtzman is from and still lives in St. Louis!!!!!

  • In reply to crackboy:

    I missed that...good catch. That little fact does add some insult to injury!

  • In reply to crackboy:

    Don't get too down on Leon Durham...I have no idea why he gets a pass on this, but Ryne Sandberg spilled Gatorade all over his glove the half inning before Leon made his infamous error. Somehow Ryne gets sainted and Leon's a goat.

    Also, Eckersley admitted to being a drunk when he was with the Cubs. Great for him that he cleaned up his act, but you can't fault the Cubs for making him someone else's problem.

  • In reply to UncleBouncy:

    I remember the Sandberg misplay too...and I agree that Durham got too much flak. There was a lot more to the '84 collapse than that one play. I had a friend who actually told me at the time, "Buckner would have never made that error"...of course, we know what happened in Boston two years later.

    The one thing we fans always have is the advantage of hindsight...so making these lists can be a little like being a Monday morning quarterback. At the time, no one knew that Eckersley or Willie Hernandez or Bill Caudill would do as well as they did. And in the case of Caudill, many experts praised the Cubs for being able to get Pat Tabler, who was a nice prospect at the time. But that's what made the list fun for me...it gave me a chance to look back and realize how unpredictable the game can be. The Cubs have also had deals work out there way unexpectedly (check out the best trades list on this site) I will have to say, though...some of the deals on this particular list looked pretty bad even at the time, especially the Lee Smith deal.

    What do you think of the latest big trade for Matt Garza, by the way?

  • In reply to UncleBouncy:

    As an A's fan (yes there are 4 more of us) I have to thank the Cubs for helping out a small market team.

    We have given you indirectly Carlos Pena for this year. Good Luck

  • In reply to wings9798:

    Glad to help you guys out ;)

  • In reply to UncleBouncy:

    I would also add the Juan Pierre trade as well. I know Nolasco hasn't been great but I would much rather go into the season with him as my #5 starter then Carlos Silva. At the time I could not believe we gave up three legit pitching prospects for what wound up one sub-par year of Pierre.

  • In reply to 10withamop:

    Nolasco made that deal for the Marlins and I agree that I'd like him better as a 5th starter right now. Though I will say not having to watch Sergio Mitre take the mound lessens the blow a little bit.

  • In reply to UncleBouncy:

    How about these deals:

    Tom Gordon to Houston for Ross Rohlicek & 2 players to be named later

    Bill Mueller & Cash to SF for Jeff Verplanke

    Greg Maddux for Cesar Izturis???

    Josh Hamilton to CIN for cash??

    David Aardsma & Carlos Vazquez to the Sox for Neal Cotts

    Ricky Nolasco, Renyel Pinto & Sergio Mitre to Florida for Juan Pierre?

    Omar Infante & Will Ohman to Atlanta for Jose Ascanio?

    All of these are "winners" from Jim Hendry

  • In reply to the1tab:

    Yikes!! There's just no way to make a Cubs bad trade list a short one is there? I'm giving him a pass on the Hamilton deal because the Cubs never planned on picking him -- really, nobody did. Any team could have had that Rule 5 pick from the Cubs for a little cash and the Reds were the only team interested in picking up a Class A outfielder with all sorts of issues. And you have to remember, the Cubs were a contender then, they couldn't afford to stash that kind of player on the roster for a full season the way a rebuilding team like the Reds could.

    The other trades are hard to explain away other than, Sergio Mitre. Of all the players we gave up, I'm glad Sergio Mitre was one of them. I used to turn the channel every time he entered the game.

  • In reply to UncleBouncy:

    Lee Smith was never that great a pitcher. He would constantly give up gopher balls in the 8th or 9th inning that would make the Cubs lose. Constantly.
    The only reason he made the HoF was his luck in having a long career, where he often played on teams that could give him a big lead that even he couldn't blow.
    Eckersley was another story. That was a huge loss.
    In 1990, he had the greatest year a closer ever had.
    Look it up.

  • In reply to JoeP:

    I think the Lee Smith deal was catastrophic in two ways that are unique:
    1) They turned down a Cy Young award winner and took two scrubs instead.
    2) It forced them to make a deal one year later to acquire Mitch Williams, who was far worse than Smith, for Rafael Palmeiro, who'd easily be a a HOF'er if not for the steroids scandal, and Jamie Moyer who's won tons of games over his career.

    And I don't think Lee Smith was that bad. He had his share of adventures, but overall he was one of the best closers we've had here.

    Totally agree about Eckersley in '90 by the way. That was a phenomenal year. Decided to include '92 because that was the year where he finally got the recognition and awards he deserved -- but '90 was his best overall season, no question about it.

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    Although not mentioned on the list, Manny Trillo was part of the 1980 World Series Champion Philadelphia Phillies. Trillo also was along with Ken Holtzman and Bill North a part of the World Series Champions in Oakland six years earlier. Starting with Brock, the Cubs have either traded or lost (via free-agency) several players to teams that have so far combined for at least a whopping 20 World Series Championships! You heard right. TWENTY!

  • fb_avatar

    I have a list (at least partial) of several Cubs players that have won World Series Championships while wearing other teams' uniforms, after being traded, released or lost via free-agency:

    - Lou Brock (St. Louis Cardinals, 1964 and 1967)
    - Ken Holtzman (Oakland Athletics, 1972-73-74)
    - Billy North (Oakland Athletics, 1973-74)
    - Bill Madlock (Pittsburgh Pirates, 1979)
    - Manny Trillo (Philadelphia Phillies, 1980)
    - Rick Monday and Burt Hooton (Los Angeles Dodgers (1981)
    - Bruce Sutter (St. Louis Cardinals, 1982)
    - Willie Hernandez (Detroit Tigers, 1984)
    - Dennis Eckersley (Oakland Athletics, 1989)
    - Joe Carter (Toronto Blue Jays, 1992-93)
    - Greg Maddux (Atlanta Braves, 1995)
    - Joe Girardi (New York Yankees, 1996, 1998-99-2000 as player,
    and 2009 as manager)
    - Alex Arias (Florida Marlins, 1997)
    - Jose Vizcaino (New York Yankees, 2000; St. Louis Cardinals,
    2006, although inactive during postseason)
    - Mark Grace and Miguel Batista (Arizona Diamondbacks, 2001)
    - Bill Mueller (Boston Red Sox, 2004)
    - Jon Garland (Chicago White Sox, 2005)
    - Jamie Moyer (Philadelphia Phillies, 2008)
    - Chad Gaudin (New York Yankees, 2009)
    - Mike Fontenot (San Francisco Giants, 2010)
    - Ryan Theriot (St. Louis Cardinals, 2011; San Francisco Giants,

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