Why didn’t they trade for Santana?

A common question asked in any 2008 NY Yankees preview is: “How long before the Yankees are wishing they made the Santana deal?”

This is an expected question and one that will undoubtedly hang over the Yankees, however stupid it is.

What I think is interesting, is the Red Sox have not received the same level of second guessing, which I can only assume is a byproduct of winning the World Series.

Maybe it’s because I’m a Yankee fan and have a strong disdain for the Red Sox, but I don’t think they are by any means clearly the best team in baseball. I know – they won the World Series and they’re bringing back the same team. Tough logic to argue with, but they’re not really the same team right now. (Also, as a Yankee fan I think by the end of the season the Yanks were better – and I know, the Yankees lost to the Indians and the Red Sox beat them. But in a 5 game series, the Red Sox would have lost to the Indians, too.)

The Red Sox rotation, as of right now:

1 – Dice-K, 2 – Lester, 3 – Bucholz, 4 – Wakefield, 5 – Colon

Once Beckett comes back, he becomes the number 1 and pushes everyone back. That’s a decent rotation, but is it a strength? Well, if the Yankees’ rotation is considered a weakness, then I don’t know.

Maybe Beckett/Dice-K is a better 1-2 than Wang/Pettitte but over the course of the regular season (in terms of wins), it’s close to a push and probably decided by who stays healthy. Right now, advantage Yankees.

Wakefield and Mussina are similarly a push as both are veterans who have struggled recently. Then you get youth vs. youth. Lester/Bucholz vs. Hughes/Kennedy/Chamberlain, all of whom for both teams will likely have innings concerns. If nothing else, the innings concerns would give the Yankees the advantage simply by having more pitchers, since most everyone will agree that all 5 should be good (and maybe great) pitchers.

So at this point, I just really don’t think there is a clearly better rotation. And if Beckett’s injury is serious, the Red Sox will definitely have problems relying on Colon and/or Tavarez all year.

So what I’m getting at with all this: could the big mistake be the Red Sox not trading for Santana? If Ellsbury/Lowrie/Masterson (with another low level throw in perhaps) could have gotten it done, then the Red Sox will likely regret it. Lowrie seems to be a legit prospect, but he is blocked in Boston, albeit by the pretty terrible Julio Lugo. Masterson is projected to be a bullpen piece with potential. The big piece is of course Ellsbury, but I am not sold on him as an A-level prospect. I think Rob Neyer does a good job breaking him down and discussing Theo Epstein’s claim that Ellsbury will develop “a lot more power”:

I don’t doubt that Ellsbury’s stronger now, or that we’ll see more power in the coming years. I do want to mention that he’s not a little kid. He’s 24, older than Ryan Zimmerman, Nick Markakis, Hanley Ramirez, Ryan Braun, Prince Fielder, B.J. Upton, Matt Kemp and a whole bunch of other guys who have already established themselves as good (or great) major league hitters. That is not a knock on Ellsbury, who’s going to be a fine player. But he was 23 last season and posted a .298/.360/.380 line in the International League, and that’s not typically the profile of a future superstar outfielder.

Fortunately, Ellsbury doesn’t have to carry the team. When Johnny Damon reached the majors with the Royals in 1995 — by the way, he was only 21 — he was considered the franchise’s possible savior, drawing comparisons to George Brett. But of course the Red Sox don’t need a savior, and if he’s the fifth- or sixth-best hitter in the lineup nobody’s really going to mind much.

A “lot more power,” though? Well, maybe. When Damon was 23, he hit eight home runs. When Ellsbury was 23 (last year), he hit five. From 24 through 26, Damon averaged 16 homers per season. Could Ellsbury do that? Sure. At 6-foot-1 and 185 (listed) pounds, he’s bigger than the young versions of Willie Mays and Hank Aaron. But Damon never did become a superstar. And Ichiro hits them a long ways in BP, too.

So while Ellsbury will likely be a nice player, how much better is he really than Coco Crisp? And he’s 24 – three years older than Phil Hughes. A 24-year old CF with speed and plus contact is much easier to find than a 21-year old potential ace. While most people saw Santana as unnecessary and costly for the Red Sox, truth is they probably needed him at least as much as the Yankees, if not more.

And the hidden storyline here: this must be making C.C. Sabathia’s agent very excited, as there is a very good chance there could be an old fashioned NY-Boston bidding war next offseason.


3 responses to “Why didn’t they trade for Santana?

  1. You have Wakefield in the rotation twice… I know he’s a knuckleballer but I don’t think that’s gonna happen. 🙂

    I guess you mean Clay Buchholz as the No. 4?

    I don’t understand why people are so enthralled with Lester – his minor league numbers (3.33 ERA, 1.31 WHIP) don’t compare to Kennedy (1.87, 0.97) or Hughes (2.09, 0.86). He’s an inspiring story, but why is he being portrayed as Boston’s answer to Kennedy or even Hughes? More likely he’s Boston’s answer to Jeff Karstens (3.48, 1.27).

  2. I was disappointed with Bartolo Colon’s performance the other day…. Yea I also think the Yankees HAD TO pull off that trade for Santana… They are going to regret not pulling the trigger for that guy in the post season.

  3. Ha, yeah good catch on the Wakefield thing.

    Those are some interesting numbers on Lester. I remember back when he and Hughes were both prospects, most of the Baseball America people rated Lester higher, sometimes simply because they liked them both and Lester is a lefty.

    So I think Lester’s stock has fallen some, but it will certainly be an interesting season- we’ll finally get to see what all these players can do for a full year.

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