Our Man in Chicago


It’s been a tough couple of months in Boston. The Red Sox went from a virtual playoff lock and World Series contender to missing the playoffs, firing their manager and seeing their long-tenured and well-respected general manager depart for a new challenge with the Chicago Cubs. Change has come to the AL East, change that seemed hard to imagine a year ago. Now that Theo has moved on and no longer runs the Yankees’ biggest and baddest rival, he’s more free than ever to explore a more functional working relationship with long-time nemesis, Brian Cashman. Indeed, one of the more interesting things to watch about the new leadership on the North Side of Chicago will be the extent to which Epstein and General Manager Jed Hoyer find Brian Cashman to be a go-to trading partner.

Photo credit: Aaron Houston for the New York Times

While there certainly isn’t any type of formal prohibition on trading between fierce rivals, Epstein and Cashman weren’t ever really free to pursue a trading relationship during their tenures atop their respective organizations. Despite the fact that a mutually-beneficial deal could have existed at least in theory, the constraints of the rivalry, pressure from ownership, and glare of the media made it extremely unlikely. Intra-division trades aren’t too frequent. Trades between the biggest rivals in baseball almost never happen. The last time the Sox and the Yankees matched up on a deal was back in 1997 when they swapped Tony Armas and Jim Mecir for Randy Brown and Mike Stanley. Neither Cashman nor Epstein were General Managers yet, and Epstein was just 24 years old.

Despite the fact that they worked for rival organizations, Epstein and Cashman have always seemed to get along. This makes sense, as they share a lot in common. As general managers, they were both in big markets with a lot of money to spend. They had high-profile owners and sometimes messy decision-making apparatuses. They were under harsher media scrutiny than anywhere else, and they operated with the pressure to win every year. Setting aside their professional competitiveness, one has to imagine Epstein could empathize with Cashman when he got overruled on Rafael Soriano, and that Cashman felt similarly towards Epstein as the Sox season spiraled out of control and ownership pushed Terry Francona out the door. They’re not so different, Epstein and Cashman.

They could be eager now to explore a working relationship. One has to imagine they’re at least curious to match wits in a trade negotiation, to experience up close what they’ve observed from afar over the past decade. For now there doesn’t seem to be an obvious fit between the Cubs and the Yankees, unless the Cubs were willing to trade one of their starters now. If the Cubs fall out of contention this summer and look to shed payroll and get prospects in return, could they make Ryan Dempster or Matt Garza available? And would Cashman be ready to deal? It’s an interesting question, and the burgeoning dynamic between the once-forbidden partners will be something to watch over the next few years.

Categories : Musings
  • Steve

    Garza is interesting ,

    1- Good Stuff
    2- Big Time Competitor
    3- AL EAST tested
    4- Does well against Boston

    Big time Pass on Dempster !

    • Holy Ghost


    • Mike Axisa

      It’s funny how Garza went from headcase in 2008 to big-time competitor now.

      • Steve

        Mike a headcase is Carlos Zambrano . not Matt Garza.

        • Mike Axisa

          That’s not what people were saying before Game Seven of the 2008 ALCS.

          • larry

            true .. but i still like Garza. lol

          • Mister Delaware

            Narratives change all the time. Michael Young was once seen as the prototypical perfect teammate / team player. Then he complained about being switched off positions for better players twice and suddenly the media … wait … nope … that analogy doesn’t fit.

    • Brian S.

      I actually like Dempster. He makes too much money but he’s actually a pretty good pitcher.

  • UYF1950

    Interesting theory on the possible future dynamics between the participants. Would very much like to see how it plays out.

  • Rich in NJ

    I prefer that they opt for Darvish and/or in-house pitching options.

    • Monteroisdinero


    • Cris Pengiucci

      While I’m for exploring Darvish (definitely prefer going after him instead of Wilson), I’d have to hear what the Cubs wanted for Garza before making that decision. I, too, would love to see the in-house options become viable long-term solutions.

  • BJ

    I’m mostly surprised that there’s been a picture of the two of them taken together. Where was that snapped?

  • Brian S.

    How come in every picture of Theo Epstein he is holding out his arms like that?

    • Plank

      It’s his dickhead Gordon Gecko power move.

    • Mister Delaware

      He saw Eddie Vedder hold his arm out once.

    • nedro

      Jedi mind trick.

  • Jesse

    Maybe Theo should just trade Garza to the Yankees for scrubs just to stick it to the Red Sox :)

    • Soriano Is A Liar

      Then he should try and get the Sox to take Soriano. THAT would stick it to them lol

  • UncleArgyle

    Maybe we could dumb Texeira on them. They actually have the cash to pay him and need a first baseman. Yanks can just put Montero or Swisher at first.

    /Wishful thinking’d

    • Jesse

      Or they can take A-Rod who can’t hit in the postseason and the Cubs won’t be sniffing postseason play anytime soon, and they need a third baseman!


      • FIPster Doofus

        Stop ending every one of your posts with that annoying /’d meme.

        • Jesse

          Stop starting your handle with the annoying Sabermetrics meme…

          • FIPster Doofus


            • UncleArgyle

              Can’t we all just get along?

              Rodney King’d

              • Plank


                /most annoying meme that won’t go away’d

                • Jesse

                  Who started the /’d meme anyways?

                  • JobaWockeeZ

                    Definitely not anyone on RAB….

        • BJ

          /unreasonable expectation’d

    • Slugger27

      well the big obstacle is that he has a full no trade clause. but that idea does make some sense for both sides.

  • YanksFan

    Another thing they have in common is how young they were when they became GM’s. For all the talk about Theo being 28 and the youngest ever GM (a month shy of 29), Cash was about 4 months shy of his 31st birthday. Cash is only 6 years older than Theo.

  • dan l

    I like the thought of trading Swisher to the Cubs for Marshall and Baker if the Yankees would entertain the idea of signing free agent David DeJesus for right field.

    • Steve


    • FIPster Doofus

      David DeJesus couldn’t carry Swisher’s jock.

      • larry

        Personally i don’t care what they do with Swisher.

        Im sick of Swish getting a free pass. he’s DOES NOTHING in the playoffs ! . . Maybe David DeJesus can actually a hit in crunch time. Because we ALL know Swish can’t

        • Jesse

          Someone to respond with Swisher’s struggles in the postseaon with SSS in 3, 2, 1…

          • Jumpin’ Jack Swisher

            Some things you are better off ignoring, like the guy picking his nose on the subway and/or the guy using a postseason’s worth of games as proof of anything.

            • Reg


        • FIPster Doofus

          This is such terrible logic. You’d downgrade significantly from Swisher to DeJesus on the off chance that DeJesus hits in “crunch time”? You do realize that’s not a skill, right? Swisher could easily win the World Series MVP next year for all you know. Just because his career in the playoffs has sucked so far doesn’t mean it always will.

          Bottom line: He’s a better player than DeJesus, and it’s not close.

        • Monteroisdinero

          I’d make a comment about our 10.25M right fielder who can’t run or throw but I am always bashing him so I am not allowed.

          But….My absolute favorite Swisher play is when he runs to the wall with his back to the infield, climbs the wall with his spikes planted and reaches for the ball that lands in the…..

          15th row.

          • FIPster Doofus

            He’s no Greg Golson.

          • Stratman9652

            Let me guess, you would rather have Golson out there right?

            Serious question: What makes you think he would be a better option? I just don’t understand what you see in him that the rest of us, not to mention the half a dozen other organizations that have let him go don’t?

          • Mister Delaware

            This makes total sense, harping on something completely immaterial. “I’d be so much less likely to criticize if he simply ran back to the wall then slowed to a trot as it left the park.”

            … and now for the meme thing …

            /jerking off motion’d

    • Jesse

      How about Swisher, Phelps, Romine, and Betances for Garza, Marshall, and Baker, while signing DeJesus to play right?


    • steve (different one)

      Silly question: if this is a good move, why don’t the Cubs just sign DeJesus and keep their players?

      • Jesse
        • steve (different one)

          That’s my point. If Swisher to Dejesus wasn’t a large downgrade, the Cubs would just sign DeJesus themselves. If it is a large downgrade, the Yankees prob wouldn’t want to do that just to bolster an already excellent bullpen.

    • JobaWockeeZ

      I like the thought of trading Swisher to the Cubs for Marshall and Baker for a useful starting pitcher if the Yankees would entertain the idea of signing free agent David DeJesus Carlos Beltran for right field.


      • Cris Pengiucci


        Or not, but we get your point.

  • Mark in VT

    Cashman, Theo, and GM Neal Huntington from the Pirates (and Buster Olney) are coming to Vermont November 12th to do a round-table discussion. Proceeds go to the Vermont Farm Disaster Relief Fund. Check out the website here to grab tix or make a donation.
    I’m going with a bunch of Red Sox fans (in the cheap seats). It should be very interesting.

    • Brian S.

      I say Cashman knocks out Theo by the fifth round.

  • http://none Favrest

    Dejesus would hit some out with our short porch ala Damon. He can play the outfield very well too. If we want pitching, we’ll have to trade something to get it. Swisher isn’t the reason the Yankees lost to Detroit anymore than a dozen other Yankees are. He has played well here since being acquired to be a role player off the bench. That position was Nady’s to lose, and he lost it.