Toronto's General Manager, J. P. Riccardi, has already come under fire, at home and in the national media, for his Roy Halladay publicity tour. Halladay "rumors" dominated the headlines for most of July, but the Blue Jays failed to find a trading partner in the end. It remains to be seen whether Riccardi will wish he had accepted the reported offer from the Phillies which included either J.A. Happ or Kyle Drabek and Dominic Brown or Michael Taylor. If Toronto ends up trading Halladay this offseason for a package that doesn't include two players the equal of what Philadelphia had on the table, Riccardi will look like a bit of a schmuck, overplaying his hand just as the Twins did a couple years ago with Johan Santana.
However, regardless of where Halladay is pitching next spring, there will be at least seven general managers spending the winter asking themselves "What if...?" One team will take home a World Series trophy and that lucky GM will tell his fan base, "See, we really didn't need Roy Halladay?" But whether he admits it or not, even he will have images of the Doc's gravity-defying repertoire flitting through his mind's eye right up to the final out of the season. And the seven playoff competitors who fall short...well, they'll be having trade deadline nightmares for years to come, particularly when several of the vaunted prospects who they refused to consider parting with never reach their potential, as is inevitably the case with the majority of top prospects.
I'm going to assume that Riccardi was especially reluctant to turn Doc over to another American League team (particularly the Rays, Red Sox, or Yankees), where he could make a triumphant return to Toronto half-a-dozen times in the coming two seasons, so I'll focus my comments on National League contenders.
If the reigning champions, the Phillies, don't win the World Series again this year or next, they will probably be the team kicking themselves the hardest, because if they had been willing to part with any three of their top four prospects, they probably could've guaranteed themselves a dynasty. However, by adding Cliff Lee, they may have found a way have their dynasty and their "future stars" too. Lee is somewhere between 80% and 90% of the pitcher Halladay is, but he cost not a single of Philadelphia prized prospects. The distressing question for Phillies fans is whether having a rotation full of left-handers (Lee, Hamels, Happ, and Moyer) could haunt them in the playoffs when they come up against righty-heavy lineups like Los Angeles, St. Louis, and Chicago. Joe Blanton is the only right-handed pitcher in the Phillies rotation, although they do have some kid named Pedro rehabbing for an August return.
The Dodgers put away the AL West sometime in May, so they weren't pressed to make a splash at the deadline. But one has to wonder whether this team can succeed in October when their top two starters are 21- and 25-years-old. Both Clayton Kershaw and Chad Billingsley are on pace to pitch WAY more innings than they ever have before. Billingsley is already showing some wear and tear, having allowed 5 or more earned runs in four of his last seven starts. The Dodgers do have a veteran in Randy Wolf, who has pitched much better than his record indicates (5-5, 3.43 ERA, 1.15 WHIP, 99 K, 134 IP) and they have Hiroki Kuroda recently returned from the D.L. Kuroda hasn't been great so far, but he did have a 1.46 ERA in two postseason starts in 2008. Roy Halladay would've looked really good in Dodger Blue, but the fact is, the Dodgers don't have the prospects to make an offer equal to that which Philly put on the table, so they would've had to part with productive pieces of their current major-league roster - probably Kershaw, Billingsley, or Matt Kemp - which may have created as many problems as Halladay solved.
St. Louis may be the most improved team this trade season. The additions of Matt Holliday, Mark DeRosa, and Julio Lugo (as well as the resurgence of Ryan Ludwick) filled out the lineup around King Albert and gave Tony LaRussa the depth off the bench which he so covets. The rotation for St. Louis has been very good (3.60 ERA, 2nd to San Francisco in the NL), so the Cardinals certainly addressed their more pressing problem. They also made it readily apparent that they planned to "go for it" this season. They unloaded their top two pitching prospects (Chris Perez and Jess Todd) to get DeRosa and their top hitting prospect to get Holliday, essentially decimating the farm system. Nonetheless, they probably could've cobbled together a package including Colby Rasmus and Daryl Jones which might've been enough the nab Halladay as well. If you're going to "go for it," then sell the whole damn store! The 1-2 combo of Doc and Chris Carpenter would've given them the formula for playoff domination.
Of all the contending teams who were relatively quiet at the deadline, the Cubs are somehow the most perplexing and it probably has more to do with their impending sale than any apathy on Jim Hendry's part. The Cubs have no other reason to be conservative. They are a veteran team trying to redeeem themselves after two straight early exits from the postseason. Much of their core is either declining or on the verge of free agency, and they don't look like they have much future beyond Lou Pinella's contract (which runs through 2010). They probably could've made a run at Halladay by giving up some combination of Jake Fox, Randy Wells, Josh Vitters, Jeff Samardzija, Jose Ceda, and Micah Hoffpauir. However, Chicago was one of the few contending teams that didn't even get mentioned in the daily Halladay updates, suggesting that Hendry's hands were truly tied.