After C.C. Sabathia’s lucrative contract extension and talk of Cole Hamels receiving a similar deal, I have to think back to Roy Halladay. After their 2009 loss to the Yankees, the Phillies traded for Roy Halladay, and promptly signed him to a 3-year, $60 million deal with a vesting option for the 4th year. It’s looking like pretty much the best big-money contract in baseball at this point.

Since the trade, Roy Halladay has been the best pitcher in baseball. He’s pitched over 483 innings with an ERA around 2.40. The Phillies have built an incredibly good rotation around him. Cliff Lee and Cole Hamels are no slouches, but they are somehow eclipsed by Halladay.

It’s easy to forgot that Halladay could have been sent to the Yankees instead of Philadelphia. The Yankees offered Philadelphia Jesus Montero for Halladay, straight up. They opted to pass, instead taking Travis d’Arnaud, Kyle Drabek and Michael Taylor. Taylor was quickly traded to the Athletics, while Kyle Drabek has struggled in the major leagues. Travis d’Arnaud has developed into a strong prospect, but I think the Blue Jays would probably take a Jesus Montero + smaller pieces package today if they had the chance for a do-over.

As awesome as Michael Pineda is, I don’t know anyone who wouldn’t rather have done a Montero-Halladay swap. The Yankees, instead of the Phillies, would have the best 1-2 punch in recent memory, at  a very reasonable cost. Halladay may be getting older, but his play hasn’t yet shown any sign if dropping off. And above all of that, there’s something about having all-time-great, Hall-caliber players on a Yankee team. It just feels right that Halladay, probably the most dominant pitcher of the post-Pedro era, would play his career in pinstripes. Along with Sabathia, he’s the kind of player that reminds us of the Torre-era rotation of David Wells, Andy Pettitte, and David Cone.

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12 Responses to Roy Halladay: What a Bargain

  1. Craig Maduro says:

    Eh, I’m not sure that would have ended in a better situation overall. You mentioned Halladay’s age which is a con when compared to Pineda. Obviously Pineda has a long way to go before he’s mentioned in the same breath as Halladay, but I don’t think its too crazy to prefer the 22 year old locked up for the next five seasons far below market value. I’d also dread the presence of Jesus Montero in the division – esp. teamed up with Jose Bautista, Brett Lawrie and whatever other bats they have coming up.

    Doc would certainly have helped the Yankees in 2010 and 2011, but I think the current situation is better in the long-run.

  2. Michael P. says:

    I very vaguely remember the awesome pitching of the 90s Yankees dynasty. They have a chance to repeat the success next offseason. CC, Grienke, Pineda, Nova, Banuelos would be about as good a 1-5 as anyone in baseball. I do think its imperative the Yankees remember the success of those teams was based on excellent pitching and timely hitting, not excellent hitting and timely pitching. Hard decisions are going to have to be made about signing Swisher, Granderson, and Cano to extensions though. I honestly do not see how the Yankees can keep Granderson and Cano and sign a high end pitcher like Hamels/Cain/Grienke if they are serious about the the payroll limit.

    • T.O. Chris says:

      No thanks on Grienke. I’m not a huge fan of his anyway and he has a wild card that, whether you want to make fun of someone for worrying about it or not, has to be factored in the decision to sign him. At the length and money he’s going to deman I’ll pass.

      I think I’m in the minority on this one, but I REALLY hope we DON’T re-sign both Cano and Granderson. I’ve just resigned myself to giving a 31 year old Cano a 7 or 8 year deal, but Granderson needs to be gone either before 2013 starts, or after it ends. Keeping both will be a disaster sooner than later. I have no desire to watch a declining Arod, Teixeira, Granderson, and Cano all in one lineup.

      Also after Lincecum’s 2 year deal I think you can all but scratch Cain off the free agent list for next year. They now know they can’t keep Timmy long term, I expect a long term deal with Cain before the All-Star break. That guarantee 7 years of Cain, and the next two with Cain and Lincecum. It’s their best strategy available to them.

      • Craig Maduro says:

        Granderson can probably remain productive through his 35 season if not 36. Maybe not MVP productive, but still solid.

        Whether the decline happens, earlier, later or on schedule, the concern is still real and it just emphasizes how important it is for the Yankees to start addressing the offense now before they’re left scrambling.

        • T.O. Chris says:

          I think you are being WAY too optimistic on that one. He has very light on base skills, strikes out as much as anyone in the league, relies on his bat speed for 100% of his power production, and can only play CF because of his ridiculous speed.

          With Grandy you’re looking at a 20 HR LF, striking out 140-160 times by 34-35. His production won’t slowly decline, it will fall of cliff from one season to the next. His bat speed will determine it all, once that slips his offense will be taken like a thief in the night. This is coming from a HUGE Granderson fan too.

          • Craig Maduro says:

            Maybe I’m too optimistic, but I think you’re too pessimistic on this one. If we meet in the middle we should be fine. Players don’t just fall flat like they used to. The K’s are troubling but his BB% has been double-digits since 2008.

            I’d definitely prefer an extension that expired after his age-34 season, but if it has to go through age-35 I don’t think it will be such a terrible thing.

            • T.O. Chris says:

              You have to look at skill set to determine that. You can’t just say “it’s 2012 no one falls off a cliff these days, ink him up”. It’s just not smart buisness. You have to look at each player on a case by case basis. In this case Granderson is a sub 200 pound center fielder who generates 100% of his HR power via his bat speed, one that goes so does the power. Plus he’s only valuable in an extension if he’s playing CF most of the contract, if he moves to left field 2 years into a 5 or 6 year deal it’s not worth it. He doesn’t take routes to balls well enough to stay at center once his speed falls off. There isn’t a worry of that this year or next, but if he starts to slow down in 2014 or 15 you’re looking at a bad decline in offensive production, with a move to left field. The combination is a terrible outcome to an extension.

              • Michael P. says:

                I honestly think the Yankees should have explored the possibility of trading Granderson this offseason. He has this year and a team option for next year and is coming off his career best season. You can slide Gardner into CF and that would only add to his value since much of it is tied up defensively.

                However on Grienke I can easily flip the argument that pitching in NY would not cause him to have a break down, but instead alleviate it. Hell that was like what 6 years ago? Besides he will be cheaper than Hamels and if you look at the numbers just as good if not better and a year younger. If signing Grienke to a “Weaver deal” instead of Hamels to a “CC” deal can be done I think it would be a better investment of the teams resources and allow more payroll flexibility.

                Cain is probably staying in San Fran, but I truly believe Hamels is going to be a free agent based on what his agent said about the Weaver deal. Wouldn’t say no to any of the three but if were going to split hairs here

              • T.O. Chris says:

                Actually you can’t… New York has never alleviated any pressure on any player, ever. It’s whether or not you thrive on pressure, or have the ability to shut out said pressure that allows you to play in the big markets. Grienke hates giving interviews at his locker after games, in Kansas City or Milwauke you have a handful of reports around the lockers asking questions, in New York you have 20 plus. Add in all the extra pressure nationally that cover even the smallest Yankee flaw and you have a pressure cooker. He may be able to deal with, but you will never know until it happens, and by then it would be too late to fix.

                Yes it was six years ago, but SAD doesn’t dissapear. It’s something you deal with your entire life, my ex-roommate still has problems with these things and it can drastically effect mood from day to day.

                Grienke isn’t going to sign a Weaver deal, he’s going to get 7 years and somewhere around 17-20 million per year. His youth and career numbers guarantee that. Both are going to be paid like aces, but I would have doubts about Grienke’s ability to actually pitch like one.

                At the end of the day I think this whole conversation is moot anyway. The Yankees aren’t going to sign any of the above pitchers, they have CC, Pineda, and Nova, they may go after another middle of the rotation guy to fill Kuroda’s spot, but I imagine they will want to go with Banuelos and Hughes in the 4 and 5 if at all possible. They may bring in some back of the rotation guys to compete with them, but if Hughes shows any kind of life this season they won’t be shopping for a 1 or 2 starter come FA.

  3. lolwhat says:

    Uhh, no. Jesus Montero is not greater than the pack of Travis D’Arnaud, Kyle Drabek and Anthony Gose (who was received from the 1-for-1 trade for Brett Wallace, who was received for the 1-for-1 trade for Michael Taylor).

  4. bpdelia says:

    No you cant count hose man. That’s two deals later. Drabek is looking like a disaster. Seems to me banuelos, montero and a heathcott might have been a better deal. Montero straight up no.

  5. obin says:

    I think Pineda has to walk much time mentioned in the same position as Halladay. I think there should be disagreement about this. Thank you for the post.

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