Where to, Doc? (Update!)

Matt Holliday was the first big name to move before the deadline this year, but with him now in a Cardinals uniform, there’s some big names still on the block. But of the players still to change clubs, only one will vault his new team to the front of the pack among contenders for this year’s crown.

Roy Halladay is the cream of the likely-to-move crop, and while a number of teams have shown interest, Philadelphia has been and still is the most likely landing spot. The Cardinals have been thrown around, but after the Holliday deal it’s unlikely they’ve got the chips to satisfy Blue Jays GM J.P. Ricciardi, who’s asking for the moon, sun, and constellations to be named later. The Brewers might have the prospects to get the deal done, but after trading top prospect Matt LaPorta in the Sabathia deal last year, I have a hard time believing they’d be willing to strip their farm system again. And while they’d be getting another season of Halladay, Milwaukee couldn’t come up with the cash to keep Sabathia, so if you can figure out how they’d be able to keep Doc in the fold, be sure to contact Doug Melvin ASAP.

The Dodgers have expressed interest as well, but Toronto will be asking for a package starting with some combination of Chad Billingsley, Clayton Kershaw, and Matt Kemp. LA is in the enviable position of having so much of its young talent producing at the big league level, but trading away such important parts of their big league roster just leaves another hole to fill. With a sizable division lead, and a relatively healthy squad, the guess here is that LA takes their chances with a lesser acquisition, a second-tier starter or another arm in the bullpen.

Ricciardi has expressed some reluctance to trade Halladay at all. That goes double for the teams in the AL East. Let’s face it: the Yankees and Sox aren’t trading for a year and a half of Halladay. They’re driving the Brinks truck right through his living room wall and making the Jays’ lives a living hell for the rest of Doc’s career. It’s going to take a mother lode for one of those teams to make it happen.

That said, look out for Boston.

The past few weeks have been rough on the Sox, as Jason Bay’s bat has turned to sawdust along with their division lead. The top of their order is struggling. And the Sox’ personal whipping boys from the Bronx have just slipped by them for first place in the East. Why, then, did Theo Epstein trade for Adam LaRoche and Chris Duncan instead of pursuing Victor Martinez in exchange for Clay Buchholz? Boston has been rumored to move Brad Penny for weeks, and John Smoltz isn’t himself yet, but they’re not hurting for pitching depth, and the young Buchholz is big-time trade bait.

The holdup to a Jays-Phillies deal has been the Phils’ unwillingness to include Kyle Drabek, the young, potential top of the rotation arm Ricciardi wants. Buccholz only turns 25 next month, and he’s got a big league no-hitter under his belt. This is the type of guy a Halladay deal could be built on. It was only last Sunday that Halladay turned in a complete game, one-run performance against the Sox. It would take a lot to make it happen, but if it does, there’s not a team on this planet getting through a Halladay-Beckett-Lester rotation in a playoff series. I’m thinking Epstein is well aware of that.

If Boston doesn’t jump in, it’s Philly or bust for Halladay. While Ricciardi is clearly going to play his hand strong, looking for Drabek, along with J.A. Happ and other top Phillies farmhands, I think Ruben Amaro will be able to keep one of those young pitchers in the fold and still get the deal done. Toronto needs to move salary, and any GM taking Vernon Wells or Alex Rios off the Jays’ books had better have his resume up to date. Halladay is the biggest chip they’ve got, and he’s worth less to them over the winter than he is now or will be in a year. No matter what he gets in return, if he makes this deal, Ricciardi won’t be popular in Toronto. But being popular isn’t his job. His job is to make the Jays a contender, and the quickest way of doing that is to get the best package he can, and to do it by this time next week.

(Make it happen, Rube!)

UPDATE: The NY Post (yeah, I know), citing MLB XM and MLB Network, is saying Halladay to the Phils could be done within 24 hours. (NY Post via The700Level)

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