Cashman discusses best and worst trades with ESPN

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ESPN recently put together a short little compilation video asking various GMs about the best and worst trades they’ve made over the years. The Brian Cashman segments start at 0:31 (best trade) and 1:57 (worst trade). Here’s the link in case the video embed isn’t working for you.

Cashman has been the GM for a long, long time, but it’s not hard to pick out his best and worst deals. He calls the Alex Rodriguez trade his best — the money aspect of that deal is always forgotten, the Rangers ate so much salary that the Yankees got age 28-31 A-Rod at $16M (!) per year — and it’s interesting to hear him talk about the business impact of the trade, on attendance and cable subscribers, etc. Cashman calls the Mike Lowell trade his worst, which he’s been doing for about eight years now.

Of the top of my head, other candidates for Cashman’s best trade include the Nick Swisher and Bobby Abreu deals. The Jesus MonteroMichael Pineda swap has to be a worst trade candidate until Pineda actually pitches for the big league team. The jury is still very much out on that one, obviously. Tyler Clippard and Ted Lilly are worst deal candidates as well.

Jeter leaves game with right quad tightness
Steve Delabar beats out David Robertson for final All-Star spot
  • Justin

    How about David Justice as one of his best?

    • trr

      it was!

  • forensic

    I was gonna ask why Friedman was talking about a trade from 2006, then realized he was named GM in 2005. Doesn’t seem like he’s been there for that long.

  • briancg

    how’s the pineda/montero trade one of the worst?

    neither team has gotten anything from it. kind of a non factor trade.

    • Dalek Jeter

      Because Lowell went on to be an everyday really good player where as right now Montero has a .300 OBP (not average, but OBP) in AAA this year.

    • Different Josh

      Because Jesus Montero was the #3 prospect in baseball. You only get to trade him once. Unfortunately right now that hasn’t worked out well.

      • Cool Lester Smooth

        There’s no point in judging a trade like this until 3 years out.

        Anyone saying it was good or bad before then is just guessing.

        • RetroRob


          The A-Rod deal can be rated. The Lowell deal can be rated.

          The Montero-Pineda deal is unknown, and the one word both teams would probably use would be disappointment.

      • Slugger27

        this comment is straight out of the axisa handbook. pineda was coming off a 3 WAR season as a 22 year old with 2 strikeout pitches. thats not a fair trade for a prospect who hasnt proven anything in mlb?

        if the twins traded buxton for, say, shelby miller… you would consider that a terrible trade? one that would be worthy to be called the worst of a GM’s career?

        • JobaWockeeZ

          lol when you have to describe someone with a decent WAR, an age and things that every good pitcher has then you know you’re bullshitting.

          Montero was offered and asked for for pitcher sliek Roy Halladay or Cliff Lee. Montero was off limits for guys like Dan Haren.

          Cashman took a risk which could either work out but he didn’t have to on what will be his best chip he’s had for awhile. But keep throwing Mike’s name around thinking it’s a good insult (it isn’t).

          • Bubba

            For Halladay, it was Montero plus plus plus. They also were probably still clinging to the dream that Montero could catch.

            For Lee, didn’t the mariners back out.

          • Cool Lester Smooth

            Montero and Noesi for 5 years of Pineda+Campos is a better deal than Montero++ for 1 year of Roy Halladay or half a year of Cliff Lee.

        • Mike Axisa

          A trade can both make sense at the time and work out horribly. The Yankees traded a top five prospect in all of baseball for a pitcher who almost immediately blew out his surgery and has yet to appear in an MLB game 18 months later.

          That trade has been a disaster so far. They had one chance to trade Montero and they fired a dud.

    • Preston

      If the Pineda/Montero trade, Tyler Clippard or Ted Lilly are your worst trades in a tenure this long, you’ve done okay. But the Mike Lowell trade was pretty bad.

    • forensic

      Montero hasn’t developed yet as most have imagined, but he’s still got time (so does Pineda, but he’s also coming off a major shoulder surgery). Also, given the value he had at the point he was traded, I felt they could’ve/should’ve tried to get someone better and/or a little closer to sure thing.

    • Slugger27

      how’s the pineda/montero trade one of the worst?

      it isnt. revisionist history.

      • JobaWockeeZ

        Just because people who didn’t like the trade were written off doesn’t mean their opinions weren’t valid.

        You tried your hardest to belittle them sure but that’s not all it takes to actually refute the opinion.

    • alen

      isn’t pineda the guy that went on the DL as soon as he got to the yanks and no one could prove that his old team knew he was sick?

  • Dalek Jeter

    cool vid, but we need an update on the Jeter thing because it’s a veritable coup d’état amongst fans right now.

    • RetroRob

      Amputation is recommended.

      The Captain says he’ll play with one leg.

    • SDB

      Cashman failed. What else do you want to know?

  • jsbrendog

    yeah. fuck jeff weaver hahaha. i remember being so psyched when they got him. that bastard haha.

  • RetroRob

    It is interesting that people forget the A-Rod deal, which is his best. Obtaining a great in his prime, who will win two MVPs, while having the other team pay a large chunk of his salary is one for the positive ledger.

    The Montero-Pineda deal makes neither the best or worst. It’s too early to assess the deal so it can’t be in either column. Both have been a bust for different reasons, but Pineda may swing this into the positive side very soon. Most likely, though, it will be a few years before it can be called a great deal, bad deal, an even deal, or declare who “won the deal” no matter how hard fans try.

    • jsbrendog

      AND all he gave up was alfonso soriano.

      • I’m One

        And that trade would have looked even better if Hank hadn’t … Oh, fuck it. We’ve been through this too many times before. It was a great trade, though.

  • forensic

    It’d be interesting to see if most fans (or maybe even Cashman himself) would put the Granderson/Jackson trade more in the good category or bad category. I bet you wouldn’t get a real consensus either way.

    • Blake

      I think it was fair….neither good or bad really . The tigers clearly got the best of the deal though considering they got both Sherzer and Jackson.

    • RetroRob

      I would say he’d put it in the good category. Certainly not the bad category. He was remaking the team and the OF and needed LF’d power. Jackson would not fill that. He traded away value and got value he needed more at that time.

      Fans want one kind of deal: One where there team receives great value and the other team receives nothing. Doesn’t work that way.

      • RetroRob

        “*LH’d* power” and “*their* team”

        Oh for to bring back that brief one-week period one there was an edit button.

  • Blake

    I agree with Cashman that Arod was his best trade…..I know everyone hates him but he was an unbelievable player at the time of that trade and had his original contract stood… would have been a great value all the way through.

    • Paco Dooley

      Thinking about the A-Rod trade and the subsequent opt out and loss of that money from Texas makes me wonder why the team could not find a way to a CC type of solution – extend him to avoid the opt out. In Alex’s case it would have certainly saved money. I assume Boras wanted to maximize leverage and called the Yankees bluff.

      • Blake

        Alex had crazy leverage…..he was coming off a historic season (2007) where he carried the yanks to the playoffs on his back….he had never really been hurt ….no PED allegations ….he was goin to break all the records and save them from Barry bonds and do it in pinstripes. That was the narrative in the winter of 2007… Hal and Hank had just taken over and were inexperienced and likely were afraid to lose their best player over money….a perfect storm of events got Alex that contract. It looks terrible now and is really hampering the club but if you consider what was known at the time it’s a little easier to at least understand how it happened

        • Cool Lester Smooth

          “Hal and Hank had just taken over and were inexperienced and likely were afraid to lose their best player over money.”

          Ahh, the good old days when they cared more about winning than marginal savings.

      • RetroRob

        They wanted to do just that so they could also keep the money Texas was paying. Boras would have none of it. They just weren’t open to negotiation. It wasn’t a shock that A-Rod returned. It was a surprise that they didn’t get a better deal.

  • SDB

    Chrissakes, I can’t stand this Boston team. Tied the game 7-7, and they’re doing it with hits from fucking Brock Holt and Jose Iglesias. Still.

  • Jim James

    That was cool, it kinda humanized these guys who mostly come across as robots almost every other time you ever hear them talk. They sounded like people sitting around talking about bad fantasy trades. I guess maybe because you never really hear anyone discuss mistakes, it’s usually a writer doing that & without the actual perspective of why they made the deal at the time. Usually the way writers talk about these things is full of their schtick too, trying to impress ESPN into paying them to not really do anything but argue about stuff.

  • LW23

    He forgot the Canseco deal? That was a gem.

    • RetroRob

      What was the exact deal?

    • Steve (different one)

      It wasn’t a trade. It was a waiver claim.

  • Pasta Stumbling Sojo

    Check out this NYTimes article reporting on the Lowell trade:

    “In return for Lowell, the Yankees received three highly rated young pitchers, each of whom was involved in a previous trade that involved a big name. Ed Yarnall, a 23-year-old left-hander, was a part of the Mets organization until he was shipped to the Marlins in the package for Mike Piazza. Mark Johnson is a former first-round pick of the Houston Astros who was sent to Florida in a trade for outfielder Moises Alou. And Todd Noel is a 20-year-old right-hander who was a first-round pick of the Chicago Cubs in 1996, then was traded to Florida last season for the reliever Felix Heredia.

    Executives with other teams gave the Yankees high marks for this trade, saying all three pitchers possess excellent potential and could develop into good major league pitchers.

  • Duh Injuries

    The A-Rod trade was a no-brainer.

    The A-Rod re-signing was a shit-for-brainer.

    The best trades Cashman has made by players he acquired:

    Brosius, Justice, Chacon, Small (he got lucky with the last two.)

    The worst trades:

    Jackson, Cabrera, Kontos

    Kennedy was 8.17 ERA awful in 2008 and pitched exactly ONE INNING in 2009, besides that the 2009 Yankees Opening Day rotation was Sabathia/Wang/Burnett/Pettitte/Chamberlain (remember Wang was still considered an ace/#2 despite his injury-shortened 2008), so spare me that was one of the worst trades.

    I don’t wanna hear about Lowell either when the Yanks went on to win THREE World Championships and a pennant where the Yanks were three outs away from winning the World Series with Brosius as their everyday thirdbaseman. Nice that Lowell got World Series rings with the 2003 Marlins and 2007 Red Sox to go with the cake one he snagged with the ’98 Yanks as a cup of coffee player, he got lucky, what else? He was not “The Man” on either team and even if he was on one of them, so what? Brosius still has double the World Series appearances as Lowell, one more real WS ring than Lowell, and three times as many WS rings as a Yankee than Lowell.

    • Pat D

      Jackson and Cabrera were not worse than Lowell. They at least got SOMETHING out of those deals. They got NOTHING out of the Lowell deal. The Kontos/Stewart deal won’t be truly terrible unless Kontos becomes a top set-up man or closer for multiple years, which he hasn’t done yet.

      At least Cashman wasn’t GM during the ’80’s. He’d have no end of bad trades to pick from (Fred McGriff, Willie McGee, Doug Drabek, Bob Tewksbury, Jay Buhner, Rickey Henderson).

      • The Real Greg

        The Kontos deal is slightly leaning to the Yankees favor as Kontos has a 5+ ERA with San Fran this year and has been
        demoted to mop up duty.

        Plus Stewart has had career years in offense with the Yankees. Yes, that’s technically true.

    • Get Phelps Up

      Kontos and his 74 ERA+?

      • Get Phelps Up

        And the Yankees actually “won” the Melky trade if you look at fWAR the acquiring teams got. (1.7 to -1.3)

  • Pasqua

    As a credit to Cashman, all of his “bad” trades are in hindsight (i.e. players who turned into something unexpected after being dealt). I can’t think of one deal the man has made that made no sense at the time of the deal (i.e. “What in the holy hell did he just do?!”)

    • JobaWockeeZ

      You can negate like 80 percent of bad trades for most GMs if we’re doing this.

      • Pasquapissandwynegar

        Fine, but my point is that, even using that logic, Cashman has avoided the other 20% (obviously crappy deals) almost entirelyy.

      • Preston

        Of course, but the other 20% are the ones a GM can actually avoid. The other 80% have a lot of unpredictable variables involved.

    • The Real Greg

      The second Javier Vasquez deal was hated by the fans from the start.

      • RetroRob

        Not by me and many, many others. By baseball people, it was actually rated as an exceptional deal by the Yankees at the time.

      • Pat D

        I didn’t hate it. I thought it was a great deal.

      • jsbrendog

        plus the yankees won that trade because Boone Logan, of all people, has been an extremely useful player.

        Melky was the worst ML outfielder in his year with the Braves, Arodys is still injured and in a different org, and what was the other one, mike dunn?

        yeah Boone >>>>>>>>>>>>>>>>>>>>>>> Mike Dunn

  • Get Phelps Up

    I think the Ichiro trade also needs to be mentioned as one of his best. Definitely not the best, but it deserves recognition.

    • The Real Greg

      No matter what Axisa thinks.

    • Tom

      Cashman had practically no involvement in that deal – that deal was done at the ownership level.

      Cashman basically worked out the details and decided what org filler prospect to send back.

      • Get Phelps Up

        Do you have a link to that? I know that the ownership had alot to do with resigning him but I hadn’t heard that they were involved in the trade.

  • Rolling Doughnut

    Meanwhile Nava just put the Sox ahead in the tenth.

  • Larry W

    Worst by far was Ted Lilly and Joe torre gets an assist. This was not a big money move. Which should have sent alarm bells off. Torre simply hated Lilly…we end up getting Weaver who lost the 2003 World Series for us…them we flipped him for Kevin Brown who lost the 2004 ALCS for us! Meanwhile Lilly turned into a solid #2/3 starter who was a lefty!

    The mike Lowell trade was bad…but at the time 3b was blocked. Never understood the Clippard trade

    • Pat D

      Jeff Weaver didn’t lose the World Series. Joe Torre, David Wells and the pitching of Josh Beckett did.

  • HenryCotto

    Betemit for Swish??