In the aftermath of the Halladay trade, most commentators have noted that the Yanks just didn't match up well with the Jays' needs as far as being trading partners is concerned. But with a little creativity, the Yankees could have had Halladay while keeping both Joba and Hughes.
How, you ask? Simple. First, everyone knows that the Jays wanted Montero. The Yanks love his bat but probably won't have a position for him on the Major League club for another seven years, when Teixeira's contract expires. Montero is young, having celebrated his sweet sixteen not that long ago (yes, he did have a pony), but the Yankees could move him without blinking. The first step, then, is to put Montero up as part of the trade.
The second step is the key to the trade. The Yanks knew last summer, after their first attempt failed worse than the Challenger, that the Jays would be looking to move Halladay this winter. Right after winning the World Series, the Yankees needed to quickly, and quietly, legally change the name of Kei Igawa. The name doesn't matter, so let's say he is now legally Ted Smith. They could call up the Jays and say, "We're willing to part with Montero, Smith, and some lesser prospects too, or a Melky or Garner. Who is Smith you ask? Just the most dominant pitcher on our AAA staff. His numbers definitely indicate readiness to pitch at the major league level. We're surprised you've never heard of him, he's only our best AAA pitcher. This deal is only on the table for 24 hours though, so act quick, because we're not sure we really want to trade such a great pitching prospect."
At this point the Jays are real curious, not to mention upset that their scouts are utterly unaware of Smith. All sorts of player development people and scouts get fired. Smith's numbers don't lie, he's ready to pitch in the major leagues. Why has no one ever heard of him? They know no other team has a pitching prospect this dominant in their system. After completely gutting their scouting division, they take up the Yankees offer, only to find out a week later that Ted Smith is actually Kei Igawa. Anthopoulous is fired a day later. The scouts cannot be rehired because the Yankees already poached all of them, seeing as they were desperate for work in a down economy. The Jays don't recover for decades.
You see, it's all quite simple. The Yankees could've had Halladay and essentially wiped one of their division rivals off the baseball map with one simple legal name change. Think long and hard about that before the next time you want to praise the Yankees front office.