Yanks could pass on the top free agent pitchers now and look for better next winter

Scouting the Free Agent Market: Joaquin Benoit
2013 Winter Meetings Day Two Open Thread
Is a Garza now worth a shot at a Kershaw later? (Getty)
Garza now or maybe a shot at Kershaw later? (Getty)

Six years ago, the Yankees took one of the biggest risks in franchise history. The Twins were shopping two-time Cy Young Award winner Johan Santana one year before free agency and he was a perfect fit for the Yankees, a team in need of a workhorse ace left-hander. There were offers and counteroffers, a bidding war between the Yankees and Red Sox, and weeks of rumors. It was exhausting, really.

Santana was a perfect fit for the Yankees … except that he wasn’t. Not only would they have had to trade away some of their top prospects to acquire him, but they’d also would have had to give him a nine-figure contract extension to keep him around. Johan was also showing some signs of decline, particularly in his spiking homerun rate and sudden decreased usage of his slider. There were definite red flags. It was a risky move but the type of move the Yankees usually make, except this time they didn’t. They passed on Santana and off he went to the Mets for a mostly forgettable four-player package.

The Yankees passed on Santana for two reasons. One, they wanted to keep their young pitching. Given the state of the franchise at the time, it was the right move. Two, there was a better option coming along the next offseason. CC Sabathia, another Cy Young winning workhorse left-hander, was due to become a free agent following the 2008 season, when New York could acquire him for nothing but money (and a draft pick). It was an incredibly risky move because there was no guarantee Sabathia would actually hit the open market, but the Yankees rolled the dice and a year later they got their man. They kept their young starters and got their ace lefty. Santana, meanwhile, gave the Mets one Cy Young caliber season before starting to break down. The plan couldn’t have worked out much better for the Yankees.

Fast forward to present day, and the Yankees are in a bit of a similar situation. No, they aren’t trying to trade for a Cy Young winning ace southpaw (that would be David Price), but they are in the market for pitching and there are some pricey options sitting out there for the taking, namely Ubaldo Jimenez, Matt Garza, and Ervin Santana. Those are the three best free agent starters available right now while Masahiro Tanaka sits in posting system limbo. And you know what? None of those three guys is a slam dunk, we gotta have him starter. Jimenez was awful as recently as the All-Star break, Garza has been hurt the last two years, and Santana was awful in 2012. The track records are as sketchy as they get for a high-priced starter.

Those are the top free agent pitchers available right now, with Hiroki Kuroda off the board and Tanaka not yet available. Now, courtesy of MLBTR, here is a sampling of the hurlers scheduled to hit the open market one year from now, during the 2014-2015 offseason (2015 season age in parenthesis):

Homer Bailey (29)
Clayton Kershaw (27)
Jon Lester (31)
Justin Masterson (30)
Max Scherzer (30)
James Shields (33)

Those are six pretty great pitchers, right? Just about all of them are reasonably young too. I’d rather have any of those six over Ubaldo or Garza or Santana, that’s for sure. Obviously those guys could sign extensions between now and next winter — Kershaw, Scherzer, and Lester seem most likely to ink an extension at this time — but there’s just so many of them that one or two figures to slip through the cracks and be available next offseason.

If Tanaka doesn’t get posted — I still think they should go all out to land him if he does indeed become available at some point — I think the Yankees would be better off repeating their Santana-Sabathia strategy. Rather than pay for an imperfect solution like Garza or Ubaldo or Santana right now, they could sign a stopgap starter (Bartolo?) for this year before going hard after one (or maybe even two) of those top guys next winter. They’ll want to have as much money available as possible if, say, Kershaw and Scherzer hit free agency next winter. Or Bailey and Masterson. Or Lester and Shields. You get the point. A stray Ubaldo could gum up the works.

Would this plan be risky? Absolutely. There’s a chance all of them will sign extensions before free agency and the Yankees will be left out in the pitching cold. Is it worth the risk? I think it is when there are six (not one or two) of these guys and the alternatives are Garza, Jimenez, and Santana. That’s easy for me to say when my neck isn’t on the line, obviously. It could be that the Santana-Sabathia situation was a one-time thing the Yankees are not willing to risk again, but because they took that risk once before and it worked out so wonderfully, we kinda have to assume it isn’t completely off the table in the future. If Tanaka is not posted, the Yankees’ best course of action maybe be signing a stopgap starter and focusing on those premium arms slated to hit the market next winter.

Scouting the Free Agent Market: Joaquin Benoit
2013 Winter Meetings Day Two Open Thread
  • Jake

    if Yankees land tanaka then the rotation is 1. CC 2. Kuroda 3.Nova 4. Tanaka 5.Pineda/phelps/nuno. I believe this will be kuroda’s last season with the Yankees and they will be in the hunt big time for next years class. wishful thinking: replace kuroda with Kershaw for whatever he wants!

    • Joe

      Plus if one or even two of Pineda/Phelps/Nuno work out, Nova becomes a potential trade chip. With two arbitration years left, he might be a very attractive piece to another team and could allow NY to fill another need. You then end up with a potential rotation of:

      Nova or Pineda/Phelps/Nuno + another piece

      I realize this is mostly rosterbation, but assuming Sabathia’s 2013 was a bump in the road that would be an outstanding rotation that could set NY up for success for the next half decade.

    • JonS

      1.Kuroda, 2/3.Tanaka, 2/3.CC, 4.Nova, 5.Phelps/et al

      Until CC shows he’s better than Kuroda, he’s no longer the ace. We have had 2 seasons of this now.

      • jsbrendog

        and until tanaka shows he can pitch in the major leagues he is nothing more than someone competing for that 4th or 5th spot. it has to work both ways or no way at all

      • Get Phelps Up (looking for a new name)

        Does it really matter as long as everybody is pitching every 5 days?

    • Frank

      If your proposed rotation has CC at the top, that’s not good.

      • Get Phelps Up (looking for a new name)

        Again, if they’re all pitching every 5th day, whoever is at the “top” is pretty meaningless.

        • JonS

          During the season no it doesn’t, but if you are expecting to be a playoff team (the Yankees are expecting that right?), it matters a lot with play-in games, game 1,3, etc.

          • Get Phelps Up (looking for a new name)

            True. But you worry about that when the time comes.

    • Jimmy

      I think they should pass on all but Tanka. I hope they go all out for him. But I’ve wanted to ask a question about 2 nd base. As you know we suddenly have excess outfielders. Has anyone thought about using Soriano as a 2 nd baseman, his old position. Is that really that crazy?

      • King of Fruitless Hypotheticals


  • Bo Knows

    If Kershaw reaches FA (Which I doubt) just give him a blank check and say “Fill in how many years you want, and whatever amount of money you want”

  • Chip

    10 years, 220 million for Kershaw. Getting a left hander with his abilities for his age 27/37 season? Sign this guy up

    • xnyles

      I think 10 for north of 240 will get it done. It’s crazy but I honestly believe so.

    • JonS

      Kershaw will get $250m+.

      • Chip

        Fine, if that’s what it takes, show him the money

        • jsbrendog

          show me the money, chip.

    • Preston

      He’s younger and at least as good, if not better than Cano. The Dodgers are going to offer him huge money before he hits FA (they’re already rumored to have offered 200 million plus) I’d bet 8/200 is just a starting point. He’ll command Lee AAV with a length exceeding Sabathia. Honestly I wouldn’t be surprised if he made a run at A-Rod’s 10/275.

  • Nathan

    Go all in for Tanaka this year and only him. Hope and pray Kershaw isn’t extended and go all in on him next year. If Cliff Lee is available this year, check in.

  • The Great Gonzo

    “If Tanaka is not posted, the Yankees’ best course of action maybe be signing a stopgap starter and focusing on those premium arms slated to hit the market next winter.”

    It goes without saying that even if Tanaka is posted and signed by the Yankees that you at least have to entertain any of those 6 that would make it to Free Agency, right?

    I mean, I would take ANY of those 6 dudes over Pineda/Phelps/Nuno/Nova/201-13 Sabathia/Warren any day of the week…

  • hogsmog

    Do you really think the Dodgers are going to let the face of the franchise go easy? I don’t want to see the Yankees anywhere close to that kind of bidding war.

    • momo

      why not? its not your money. as long as they aren’t crying poverty and trying to stay under 189mil they can give him 300mil for all i care. the guy is one of the few player hitting free agency before 30 with his kind of talent. if healthy he will be our ace for 8-10 years. very rare.

    • Chip

      Said Yankee fans about Cano

  • Yankee Parrotheas

    I agree with most if the article except for the characterization of the Mets trade for Santana. Carlos Gomez has turned out or be a pretty good player although not for the Twins who traded him for JJ Hardy

    • BFDeal

      Mike did say “mostly forgettable”, not “completely forgettable”.

  • ClayDavis

    I kind of wonder if the Yankees keep their eye on Santana. He seems to be the sort of guy they’ve been bringing in lately.

    • TWTR

      If he is DFA’d then on a mL deal, maybe. His injury was very serious.

    • Preston

      If you’re talking about Johan, mlbtraderumors said they weren’t interested, although at the right price I’m sure they’re interested in everybody. I think they’d let him come to st on a milb contract and compete for a job. Not sure somebody with his pedigree would be willing to do that though.

  • Frank

    Pitchers are available via trade. Unfortunately, the Yanks’ inability to develop a farm system (despite all the hype of how good their players are) prevents them from even having a chance at Samardjiza, Masterson, Price or anyone else. Heck, the Angels just got Skaggs and Quintana, 2 young lefties with upside and under team control, for Trumbo, a good power hitter who is good, not great.

    • BFDeal

      Angels got Hector Santiago; not Quintana.

      • Frank

        Stand corrected. Still a good deal for the Angels nonetheless.

  • W.B. Mason Williams

    Nah guys, sorry. The Dodgers are floating numbers to Kershaw in the 10 year, 300 million dollar range.

    He might be the best pitcher in baseball but…just no. Not for anyone.

  • I’m a looser and a trader baby so why don’t you kill me?

    A) take Lee off the Phillies hands
    B) sign Tanaka
    C) throw endless shekels at Kershaw


  • W.B. Mason Williams

    My vote would be 6 years and 100 million for Bailey next season.

    Who knows what his market will be like?

  • TWTR

    I would never give a 10 year contract to any pitcher.

  • Dr. Grenaldine

    Two of those guys were (one still is) Red Sox(!!!!)

    Meanwhile, Phil Hughes and Joba Chamberlain are not letting the door hit them on their way out…

  • CT Yankee

    Shields gave us problems when he was with the Rays. I doubt he’ll stick around in Kansas City. Why not grab him on a deal for a few years?

    Heck, maybe we can catch swing Lester over to the dark side. But I got a feeling Boston will lock him up before the season is out.

  • CS Yankee

    Isn’t Price also a FA after 2014?

    • CS Yankee

      Looked it up, a year behind Sheilds but is expected to be moved before Opening Day, 2014.

  • Jorge Steinbrenner

    Half these guys won’t make it to free agency.

    At some point, Kuroda stops signing one-year deals. I’d put decent money on this being it on that.

    Other than Bartolo Colon, what stopgap is there?

    Get someone in here now of the non-stopgap variety. Let the chips fall where they may next offseason.

  • blee

    I dont know why signing Garza or Santana would preclude the Yanks from signing a pitcher next year…

    Kuroda got a 1 year deal right?… Yanks still would only have CC, Nova, and Garza/Ervin signed right? (other than whoever wins the SP5 job)

    so.. why not both?

    • Bavarian Yankee

      because A-Rod will be back in 2015. Well, his contract will be back at least, A-Rod probably not ;)
      So that’s Kuroda’s contract + 11-12 million.

      • CS Yankee

        Unless “trio-genesis” dooms Arod during his 2014 year long rehab.

    • Griffey’s Grotesquely Swollen Jaw

      because it’s more about available funds than available rotation spots.

  • http://www.twitter.com/mattpat11 Matt DiBari

    With or without the good class next year I’m not particularly interested in the top three non Tanaka starters this year.

    • Bavarian Yankee

      this. Tanaka or somebody like Colon this year. I’d even bet that Bartolo will be better than AT LEAST one of Ubaldo/Garza/Santana in 2014.

  • stuckey

    Pop quiz time.

    Q: What so all of the 25 highest paid players in baseball have in common?

    A: None of them played in the World Series.

    Q: What do 18 of the Top 25 highest paid players in baseball, including the Top 9 have in common?

    None of them played in the postseason at all.

    • TWTR

      CC, Tex, A-Rod, and Cano aren’t some of the 25 highest players in MLB?

      • stuckey

        Cano is as of 2014, yes. The first 3 will be too.

        Your point being?

        • TWTR

          You didn’t mention that you were referring to the last WS, but Chip seems to have perceived that, so maybe it’s on me.

          On the larger point, the Yankees have to spend because they can’t find high quality cost-controlled options.

          • stuckey

            Why are the Yankees uniquely in this position in all of baseball?

            • TWTR

              I wish I knew.

              • stuckey

                Maybe because they actually aren’t?

                • TWTR

                  They can develop talent?

                  • stuckey

                    Two of their homegrown players just signed for a collective $264m.

                    Gardner is projected as their starting LF and is apparently well regarded around baseball.

                    Nova is slated to have a secure spot in the 2014 rotation and the Yankees think highly enough of 4 others to have slated the 5th spot to one of them.

                    Do I think they’re at the top of the development game, no. But its not as bad as it’s made out to be.

    • Chip

      Yeah but that’s because teams like the Yankees, Nationals, Angels and Rangers underperformed. The Yankees won it all in 2009 with CC, Jeter, Posada, A-Rod, Burnett and Tex probably all being among the top 25 highest players

      • stuckey

        The point of course is not that it’s impossible for a team with $20m+ players to have postseason success. The Yankees of course did 4 years ago.

        The point, in our increasingly statically-driven view of the game, is to find a correlation.

        Shouldn’t some statistical correlation exists between signing the “best” players and postseason success?

        If signing players to that sort of contract is designed to increase your odds of postseason success, wouldn’t a statistical correlation exist?

        I’m not stating it does not, I’m asking if anyone know if it in fact, does?

        • Jim Is A (Bored) Peckerhead

          Finding causation would be way, way more useful than finding a correlation.

  • JGYank

    I don’t think we should wait. Scherzer, Kershaw, and Lester are probably all going to sign extensions and in Kershaw’s case, the Dodgers won’t let their best pitcher go and definitely will try to extend him. A Yankees/Dodgers bidding war will make his price more ridiculous than it already will be. The Tigers also freed up some cash and traded Fister so they definitely will aim to keep Scherzer from hitting the market. I heard Lester likes Boston but he if hits the market we could try to go after him since he’s a lefty.

    Shields isn’t young, and I wonder how he will age and pitch in a hitter’s park. Bailey is younger and we could go after him as well as Masterson. But the chances of even one of those guys signing with the Yanks are not good even if some of them get to free agency.

    I still haven’t given up on Pineda, Banuelos, Phelps, Warren, and Nuno. If we can get a cheap starter out of one of them, I’d be happy. Also, I’d do what it takes to get Tanaka. That would give us CC Nova Tanaka one of Pineda/Phelps/Banuelos/Warren/Nuno/other prospects and no fifth starter beyond 2014 when Kuroda is gone. Even if we sign Tanaka or another FA starter this offseason, CC rebounds, and one of the young guys I mentioned becomes a mainstay in the rotation, we’ll still need another starter so we can sign one this offseason and still sign someone else later on if we like what is available and maybe sign one of these guys. Plus signing a starter this offseason will help the team in 2014 as well.

  • JM

    What the hell is Cashman doing ? Pitchers are being signed and traded, I guess he is climbing buildings !

    • TWTR

      Blame for being unable to develop talent, but spending money is at the owners’ discretion.

    • stuckey

      Perhaps he’s exhausted from signing McCann, Ellbury, Beltran and Johnson and getting Kuroda to come back for another one-year deal?

    • Jim Is A (Bored) Peckerhead

      …were you hibernating for the past 2 weeks

  • daBombers

    Kershaw I believe will get a MEGA deal extension with LA…We should start dreaming that don’t happen though and act like we have a chance…But I think there are a couple pitcher being shopped try striking a deal quick and with a package that we don’t sell are whole farm system and add a starter. Then we should bring up someone from the farm system for the bullpen. I just feel we can get pitching just gotta make smart moves like we used to and not get 10 OUTFIELDERS like wow..

  • Johnny Callison

    With a rotation that is shaping up to be an “Over the Hill Gang” I wonder if the day will soon be dawning when a six-man rotation becomes the norm. CC’s numbers have been dwindling downward for the last three years, weight or no, and Kuroda, who has fizzled out down the stretch two years in a row, could benefit from the extra rest.

    Hell, it wouldn’t kill them, and one of the issues that has sunk many a Japanese “Ace” has been the workload. It’ll be interesting to see what Darvish does going forward. Is he an Irabu or a Dice-K, shot after two seasons or so? Or does he have what it takes to be an elite pitcher for the long haul? The Yankees have thrown away a lot of money on pitching that didn’t play well in the Bronx over the years, so they may be leery about Tanaka.

  • OldYanksFan

    Hey…. Let’s not forget that the tax is now 50%. So Kershaw doesn’t cost us $25m+/yr, but $38m/yr.

    It might not be our money, but let’s not act like Yankee funds are bottomless.

    It is scary enough going 10 years on a position player. I would NEVER invest $250m in a pitcher. While an Ace is great, you still look at your 1 thru 5. I’d rather have a bunch of #2’s and #3’s. Cheaper and less risky.

    • Jerkface

      The tax is on a marginal amount over the threshold. So excess over 189. Individual contracts are not taxed. So Kershaw would not be 38 million per year. If the Yankees had a 220 million payroll they would pay 15 million in tax.

  • The Tenth Inning Stretch

    Imagine the reaction if the Yankees followed up this offseason’s signing of Ellsbury by signing Lester in a year.

    • Mike

      They should be honored. We are giving them props by grabbing their former prospects.

  • D$1184

    I think I still might take a flier on Garza, if the price is right. Even if the Yankees get say, Kershaw, in the Fall of 2014, what’s the rotation for 2015:


    Are we comfortable with that? Granted, it’s hard to say before we know what we get out of those 2 this year.

    • Jorge Steinbrenner (the rarely spoken-of sibling)

      I’d be shocked if Clayton Kershaw wears anything but a Dodger uniform before the next decade.

      • Mike

        Are you saying the Dodgers are willing to overpay to sign their own homegrown players?

  • camilo

    The more you want a young ace on your team, the more likely it won’t happen…. Muy triste