Happy Halladays After All?

I don't mean to alarm anyone, but the Yankees' big trade yesterday for Curtis Granderson just might put the Phillies in position to pull off that trade for Roy Halladay that we've all been asking from Santa and Hanukkah Harry.

As Todd Zolecki points out, the Phils still have the pieces to make a deal with the Toronto Blue Jays--all the players that former Jays GM J.P. Ricciardi asked after last summer (Domonic Brown, Kyle Drabek, J.A. Happ, Anthony Gose) and others from a system that Baseball America recently ranked fourth in MLB. The Phils wouldn't pay that price then, with the prospect of having Halladay for two playoff runs, so they won't do so now. But they might not have to, either; if things break right, they could be the last feasible trade partner for Toronto, leaving GM Ruben Amaro Jr. enormous leverage.

That's where the Yankee trade comes in. To pry Granderson loose from Detroit, the Bronx Bombers parted with three players who weren't key contributors when they beat the Phillies in the World Series, but did represent a big part of the organization's young depth: almost-ready outfielder Austin Jackson, starting pitcher Ian Kennedy and lefty reliever Phil Coke.  Granderson's 2010 price tag is chump change by Yankee standards--$5.5 million--and he's due a reasonable $18.25 million for the following two seasons with a $13 million club option or $2 million buyout for 2013.  Still, that's an obligation of some significance for a team supposedly looking to trim payroll slightly, still waiting on negotiations with vets Johnny Damon and Andy Pettitte and rumored to be kicking the tires on top free agent starter John Lackey. Between their payroll obligations, a relative paucity of prospects after catcher Jesus Montero and young big-league pitchers Phil Hughes and Joba Chamberlain, and the likely in-division premium they'd have to pay in talent to make a deal with AL East foe Toronto, the Yankees suddenly look like a long shot to trade for Halladay. 

And if they're out, the Red Sox might be, too. 

This was the case two winters ago, when the Yanks and Sox were considered the leading contenders to trade for then-Twins ace Johan Santana. But it soon became clear that New York and Boston were more interested in keeping Santana from the other than paying the steep price in talent and dollars to bring him on board. Similarly, if the Yanks turn away from Halladay, Boston might do so as well: they already have a pretty darn good rotation front four in Josh Beckett, Jon Lester, Clay Buchholz and Daisuke Matsuzaka, and likely don't want to part with either of their top prospects Casey Kelly and Ryan Westmoreland plus Buchholz, then have to pay Halladay some $100 million to hang around for the next five years. Besides, baseball thinkers from Joe Sheehan to Bill Simmons argue that the team's needs and priorities lie elsewhere. 

Those two AL East behemoths aren't the only other potential destinations: the two LA teams long have been rumored to be in Halladay too. But the Dodgers, wracked by their owner's divorce, pretty clearly can't afford him--evidently they felt they couldn't even risk Randy Wolf accepting arbitration. The Angels could, but it isn't clear they can match up with the Blue Jays on a trade and presumably their first goal will be to retain free-agent ace Lackey. If he signs elsewhere, we can worry about LA of Anaheim. It's also not clear that Halladay, who has a full no-trade clause he's reportedly said he'd waive for the Phils, Yankees and Red Sox, would allow a trade to a west coast team. (I'm guessing he would in the end, but that could be one more obstacle.)

That leaves the Phils, who can make a trade for Halladay and presumably could afford him (or Cliff Lee, but not both) long-term. The team's alleged $140 million budget for 2010 presents a problem, but that probably explains why they're supposedly shopping Joe Blanton (and FWIW, dealing Cupcakes to clear payroll space for Halladay is about a zillion times more palatable than doing so to afford Brandon Lyon). The biggest problem is that everything likely would have to happen at once: trading Blanton to free payroll and hopefully add a prospect or two, simultaneously with a deal for Halladay that might or might not include that prospect/s. 

Baseball trades are tricky, and the degree of difficulty rises exponentially as additional teams get involved. But it's a reasonable guess that this the "groundwork" Amaro and his crew have been trying to lay in Indianapolis this week. And if it doesn't happen before the calendar flips, that's no reason to despair: Santana ultimately went to the Mets, for a package of prospects considerably less impressive than what the Phils sent to Cleveland for Lee, on February 2, 2008. By then, the Twins realized that their choices were to make that deal or watch the pitcher walk away after the '08 season for nothing more than picks in the next draft. This essentially is the scenario we're hoping for.  

So it's something to keep in mind in the weeks and maybe months to come. And it's a lot more interesting than contemplating the uses of Ross Gload

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