Yankees Thinking of Trading for and Not Signing Halladay

When Yankees general manager Brian Cashman didn’t trade for then Twins superstar pitcher Johan Santana he often cited his distaste for giving up prospects and huge amounts of cash in the same deal.

Until recently it seemed that his thinking would be the same this time around with current Blue Jay superstar pitcher Roy Halladay. Now, according to Joel Sherman of the NY Post, it seems that Cash and the Yankees front office are mulling the possibility of trading for Halladay and letting him walk after the 2010 season in order to collect the two draft picks they would be entitled to when he leaves.

Sherman wrote:

One faction of the Yankee front office has advocated trying to trade for Halladay, but not extend his pact. That way they would get Halladay on a very good contract for 2010 ($16 million) and then offer him arbitration after the season to secure two draft picks as a way to recoup some of the prospects given up in the trade.

But that currently is not a strategy with much traction inside Yankee Stadium. The Yanks could change direction if Andy Pettitte does not return, though they believe he does want to pitch for them in 2010. Yet even in that scenario, the Yankees worry about their starting ranks.

It is an interesting scenario, but one I can hardly believe the Yankees would actually follow through on. The biggest benefit here would be that the Yankees wouldn’t have to give a soon to be 33-year-old pitcher a long-term deal. Other than that though, I don’t see much upside to this.

roy-halladaySure the Yankees could get back two of the prospects that they would otherwise be forced to deal in the form of compensation picks. But unless they really believe that Phil Hughes and Joba Chamberlain would be prepared to take on very large roles in 2011 they’re not only going to have to replace Halladay but probably Andy Pettitte too.

That would mean they’d have to give up their own draft picks and probably more than one too. Meaning, they would never get their prospects back.

There are better ways to address their 2010 rotation as well. With the first two spots locked up by CC Sabathia and AJ Burnett and Pettitte assumed to take the third spot the Yankees do actually have five guys pencilled in right now for their rotation. The issue they’re worried about is depth.

They seem prepared to have Joba and Hughes in the rotation, but if one of the top three guys go down they are not prepared to have Joba or Hughes move into their roles. So it seems to me that they’d be better off getting third starter insurance with no dire need to get ace insurance.

To me that means that guys like Justin Duchscherer, Chien-Ming Wang, and Ben Sheets might actually be better and more cost effective fits.

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