Let me start by saying that I will certainly not be unhappy in any way with Roy Halladay as the Phillies’ ace. I argued extensively last season for the Phils to make a move to get him and he is one of the top-5 pitchers in baseball, perhaps made even better in the short run by being a veteran of baseball’s best division. And now Halladay will land in the N.L. which by recent experience should mean he’ll get even more of a boost. From a performance perspective, Halladay probably becomes the best pitcher in the National League going into 2010.

But there are questions surrounding this move and its timing that can’t be ignored. First and foremost is the issue of what the Phillies have given up to acquire Halladay. Because Cliff Lee is gone as a result of this trade, the Phillies are simply replacing one ace with another. Let’s start with the trade that rented Cliff Lee for 12 starts to close out the 2009 season (and 4 brilliant playoff starts). According to mlb.com the Phillies will part with previously “untouchable” top pitching prospect, Kyle Drabek, as well as outfielder Michael Taylor and catcher Travis d’Arnaud. Combine that with the players they sent to Cleveland in the Lee deal (pitchers Jason Knapp and Carlos Carrasco, catcher Lou Marson and infielder Jason Donald) and you have a pretty high price paid for what amounts to be one pitcher.

In fairness, prospects are exactly that: an unknown commodity. But emptying close to your entire minor league tank to fill one rotation spot seems to be a bold gamble, even moreso when you consider the fact that Roy Halladay is negligably better than Cliff Lee. To boot, Roy Halladay has pitched 4 more seasons than Cliff Lee and has pitched exactly 850 innings more than Lee, meaning his treads are a lot more worn than Lee’s.

There’s a third party in this trade that has almost as much to do with it as both Lee and Halladay, and he’s as much of a gamble in this scenario as any other factor: Cole Hamels. Cliff Lee is left handed. Cole Hamels is left handed. J.A. Happ is left handed. Given the option for the next 3 seasons, Amaro clearly felt that he needed to mix a righty into the rotation and despite the fact a left handed ace (Cliff Lee) may be generally more desirable than a right handed one, there is plenty of logic in the need to mix it up. But in order for the reasoning that allows Lee to walk to pan-out, Cole Hamels needs to perform up to his potential.

The right hand-left hand thing is only as good as Cole Hamels. So gambling on him to rebound and become a premier pitcher is exactly what Amaro is doing. If Hamels comes back and pitches as well as he did in 2008, then the logic behind this move seems concrete. If not, well I guess they just traded away last year’s best postseason pitcher for nothing. Come to think of it, if the Phillies are so interested in right handed pitching, why have they traded-away their top-3 pitching prospects (all righties) in the last 6 months (Kyle Drabek, Jason Knapp and Carlos Carrasco)?

And one final area of concern: the competitive outcome of this trade. Of the three teams involved (Toronto, Seattle and the Phillies), an impartial observer has to conclude that the Jays and Mariners made out much better than the Phillies. Seattle now has two of the top-8 pitchers in the American League in Lee and Felix Hernandez. With the subtraction of John Lackey from the Angels rotation, this makes Seattle a legitimate contender for the A.L. West title. As for Toronto, in the past 6 months they’ve managed to get rid of Alex Rios, Marco Scutaro and Roy Halladay, freeing them up to pursue just about anyone they want. With the prospects they’ve acquired they’re doing exactly what they need to do in that division, which is to rebuild with very little vestigal parts.

Of course, the Phillies shouldn’t really care what’s going on in the American League, or should they? Despite an improved Braves team, a strong Cardinals team and 2 potential threats from the West, the Phillies are clearly thinking about the World Series in their personnel moves. In acquiring Halladay, the Phils have an historical Yankee killer, which may help them if they meet the Bombers again in October. But they’ve also removed that Yankee killer from the A.L. East which means Toronto’s likely to lose just about every game they play against the Yankees, a fact that can only make the Yankees’ postseason presence more of a reality.

And then there’s Boston. In signing John Lackey, Boston now has unquestionabley the best rotation in baseball. Josh Beckett. Jon Lester. A rejuvenated Dice-K. Clay Buchholtz. And now John Lackey. If their pitching staff performs anywhere near its potential they will be unstoppable. Plus they’ve shored-up their infield issues by signing shortstop Marco Scutaro from Toronto and they’re still fresh-off the acquisition of catcher/first baseman Victor Martinez. Um, and Theo Epstein made a $15.5 million offer to the Cuban version of Daisuke Matsuzaka, Aroldis Chapman. If Ruben Amaro is thinking the way he should be thinking (i.e. making decisions based on likely World Series matchups, not just focused on winning the division) he’s got to figure that he’s holding a good hand but he’s still way behind the two-headed monster called Boston and New York.

So for as great as Roy Halladay is, big questions loom. Does he make the team appreciably better than it was just two months ago? Is he worth significantly degrading what was once one of baseball’s richest farm systems? Does the reliance on a Cole Hamels turnaround have much to do with the success of this move? Does the trade make the Phillies more competitive with the American League’s elite? Only time will tell and I certainly hope this move answers all these questions in a positive way. But there are a ton of assumptions in this trade that could go dreadfully wrong, begging the question whether Ruben Amaro should have simply left well-enough alone.