Here's why Halladay deal won't get done soon

Published Nov. 25, 2009 9:33 p.m. EST

If Blue Jays right-hander Roy Halladay requires a contract extension to waive his no-trade clause, then the Jays' trade discussions could mirror the Twins' talks involving Johan Santana two years ago.

In fact, the return could end up being similarly low.

Santana was nearly 29 when he was traded for outfielder Carlos Gomez and pitchers Phil Humber, Deolis Guerra and Kevin Mulvey, receiving a six-year, $137.5 million extension. Only Guerra is still with the Twins' organization.

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Halladay turns 33 on May 14. The Red Sox, according to the New York Daily News, are "putting on a full-court press" to acquire the pitcher. But one rival executive says there is "no way" the Sox will give up both right-hander Clay Buchholz and pitcher/shortstop Casey Kelly in such a deal.

They might not give up either.

Kelly was the stumbling block in the Halladay discussions between the teams last summer, when the Jays' price was higher due to the potential for Halladay to influence two pennant races — and the reluctance of then-Jays G.M. J.P Ricciardi to trade within the division.

Although the Sox have yet to decide upon Kelly's position, they consider him a vital part of their future. Buchholz, meanwhile, projects as part of the Sox's 2010 rotation — and their rotation for the following four years as well.

The Jays, on the other hand, need not accept an inferior package for Halladay. They can keep him next season, offer him salary arbitration after he becomes a free agent and receive two high picks in return. Halladay's trade value is at least the talent equivalent of the two high picks.

There also are fewer performance questions about Halladay now than there were about Santana two years ago. Halladay produced sub-2.80 ERAs in each of the past two seasons. But in 2007, Santana sharply reduced the use of his slider, giving interested teams pause.

If Halladay truly wants out of Toronto, he could tell the Jays that he would not require an extension as part of a trade, lowering his acquisition cost. That was his position last summer, when he was still under contract for the 2010 season.

The risk now is that he could get injured in '10, damaging his free-agent value. Still, teams such as the Red Sox, Angels and Yankees would be more inclined to trade if they needed to part only with players, not tens of millions for an extension.

Little is known about Halladay's intentions; he grew up in a suburb of Denver, and might prefer to go to the west coast. His no-trade clause effectively gives him right to choose his next team.

The Red Sox would be wise to push hard for a rapid resolution on Halladay at a time when the Yankees have yet to set their budget for next season. Santana, though, was not traded until Feb. 2 in the 2007-08 offseason. The Twins' Bill Smith was a new G.M., just like the Jays' Alex Anthopoulos is now.

The Jays are motivated to move Halladay, but these will be complex, tricky, multi-layered negotiations.

It would be an upset if they ended anytime soon.