Did Philly Really Need Roy Halladay?

Yesterday one of the biggest, most complex, and - to me at least - confusing trades of the past several years was finally completed. The Phillies sent Cliff Lee, who they acquired at last summer's deadline for a package of prospects after they and Toronto couldn't agree on a package for Roy Halladay, to the Mariners for a package of prospects. Philly then sent a package of their own prospects - one nearly identical to the one they balked at less than five months ago - to Toronto for Roy Halladay and $6M. Then, Toronto took one of the minor leaguers they received from Philly, Michael Taylor, and flipped him to Oakland for Brett Wallace, who was the centerpiece of the package Oakland received for Matt Holiday just five days before Philly pulled the trigger on the first Cliff Lee deal. Got all that?

What confuses me isn't keeping all the players and parties straight. It's that I can't figure out what Philly is thinking here. Don't get me wrong, the Phillies hauled in the unquestioned best player amongst the nine on the move in this deal. But I don't get why they're willing to pay virtually the same price for Halladay now that they refused to pay in July, and to do it for a half a year less of his services.

Further, I can't figure out why they would pay that cost now, essentially decimating their farm system, to make an incremental upgrade from a top ten pitcher in Cliff Lee to a top five pitcher in Halladay, especially when they were universally lauded for making a smart deal for Lee when the Halladay price was too high five months ago. Lee is more than a year younger, has 1,060 fewer professional innings on his odometer, is half as expensive as Halladay in 2010, and they had to commit a $20M per year extension to Halladay that will carry him through his age 36 or age 37 season.

But let's back up the train a bit. In July, Toronto was apparently asking Philadelphia for J.A. Happ, Dominic Brown, and Kyle Drabek - son of former Yankee pitcher Doug Drabek. The Phils continually balked at that request, deeming Drabek untouchable and were willing to offer Carlos Carrasco instead. When a Halladay deal couldn't be reached Philly turned to Cleveland, and were able to bring in Lee for Carrasco, Jason Donald, Jason Knapp, and Lou Marson. The Lee trade allowed them to keep all the proposed chips from the Halladay deal but cost them their number 2, 3, 4, and 10 prospects according to Baseball America.

Less than five months later Philly chose to make the deal for Halladay, surrendering Drabek, as well as Michael Taylor in place of Brown and Travis D'Arnaud in place of Happ. In surrending this package they give up their number 5, 6, and 7 prospects, but did get to keep their top prospect in Brown, as well as Happ, who has proven himself capable of pitching at the Major League level.

In order to afford Halladay, and to restock their beleaguered farm system, Philly then shipped the younger, less used, less expensive Lee to the Mariners for Phillippe Aumont, Tyson Gillies, and Juan Ramirez. Aumont ranked as Seattle's third best prospect, Ramirez as their fifth. Gillies didn't rank, though he did profile as their system's top base runner and best outfield arm.

Then just for good measure, Toronto flipped Taylor to Oakland for third baseman Brett Wallace. Hypothetically, if not for the Halladay deal, Philly could have made the same trade with Oakland and received Wallace, which in turn may have prevented them from committing three years and $19M to 34 year old - and declining - Placido Polanco, who has made just 43 appearances at the hot corner over the past seven seasons. Making that hypothetical trade and saving the Polanco money might have allowed them to use that money and the money they'll be paying Halladay towards an extension for Lee.

I don't know that this was bad a series of trades for Philadelphia, but I'm unsure that they were necessary. I suppose the regime change in Toronto had something to do with it. And I suppose Seattle's apparent willingness to go all in for 2010 played a role in the decisions as well. But it boils down to Philly trading seven of their top ten prospects, and six of their top seven, to get Halladay, two of Seattle's top ten prospects, a third Seattle prospect, and $6M - or enough to cover slightly more than 75% of the 2010 salary difference between Halladay and Lee.

Now not all prospects are the same and not all systems are created equal. Perhaps the package Philly received from Seattle is comparable to what they gave up for Lee in the first place. But it doesn't appear to be. Instead, they've given up seven of their own guys - guys who they drafted and developed and know very well - to get a pitcher who's only slightly better than the one they gave had and three other prospects about whom they don't know nearly as much. It just doesn't add up to me.