The LoHud Yankees Blog

A New York Yankees blog by Chad Jennings and the staff of The Journal News


Great American Halladay?

Posted by: Sam Borden - Posted in Misc on Nov 25, 2009 Print This Post Print This Post | Email This Post Email This Post

Thanksgiving is usually a quiet time in baseball, though there have been some exceptions. In 2003, the Red Sox put on a full-court press to get Curt Schilling, with Theo Epstein even traveling to Arizona to woo the righthander and his family over turkey and stuffing.

Now, at least according to our friends at the Daily News, it looks as if the Red Sox may be gearing up for a similarly productive holiday season. This time the target is Blue Jays ace Roy Halladay and the inevitable pursuit we all expected appears to be picking up steam. The Red Sox watched the Yankees land CC Sabathia and A.J. Burnett last winter, so is it a big surprise that Boston is looking to add a marquee pitcher this offseason?

Since the Yankees aren’t just going to sit back and watch, there are two options:

1. Get involved in talks with the Blue Jays in an effort to drive the price of a Halladay trade up but ultimately pull out.

2. Legitimately try to make a deal.

In this situation, with Halladay being a 32-year-old ace and Toronto (seemingly) considering a trade within the division, the price is going to be pretty high regardless, so No. 1 almost isn’t necessary. Halladay is going to cost and, with new Jays GM Alex Anthopoulos now in charge, it’s not like the Yankees can just wait until Halladay is going to be a free agent and then pay him. Anthopoulos is surely going to move Halladay so Toronto gets something for him.

If the Yankees are truly interested, they probably need to be prepared to part with Phil Hughes/Joba Chamberlain and Austin Jackson/Jesus Montero, plus about $100 million for a contract extension on Halladay. Is that for certain? No, but it seems to be where most observers see the market. Boston is looking at Clay Bucholz plus another top prospect (the News suggests Casey Kelly, who Epstein is said to love), so this seems like a comparable discussion.

Should they do it? My thinking on these types of situations is this:

I can’t predict what the Steinbrenners want to spend on payroll but with the Yankees there is always wiggle room (and a lot of it) so I don’t factor in the extension very much at all. If the Yankees were willing to give Sabathia and Burnett – especially Burnett – a lengthy deal, Halladay is certainly just as (if not more) viable.

The player perspective is the more important issue and ultimately it comes down to whether you think BOTH prospects in the deal will become big stars. To me, I’d always be willing to trade one great prospect for an established superstar so – in my opinion – it’s only a losing proposition if both kids turned out to be huge.

If the Yankees could get Halladay for Joba and Austin Jackson, I would do it. I’m not convinced both players in that deal would become superstars and even if one did, it’s impossible to say for sure they’d even come close to approximating Halladay’s success. I’d try everything to keep Montero out of the deal (knowing the situation with Posada and the value of catchers in general) but of the other three – Hughes, Chamberlain, Jackson – I’d be less hesitant. There is no reason to believe Halladay won’t continue to be among the league’s premier pitchers, and if you have a chance to get him, I’d take it.

By the way, this isn’t about “blocking” the Red Sox. These kinds of deals can’t be only about keeping a player from another team. Or at least they shouldn’t be. Pitching is always the difference and Halladay would give the Yankees two legitimate aces, the top No. 3 in baseball (in Burnett) and probably Andy Pettitte coming in at No. 4.

That’d the best rotation in baseball and it wouldn’t even be close.

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