Yankees Could Be Perfect Fit for Halladay, but Toronto Must Get Hughes

Making up for years of lackluster player development isn't something that a team can do in one fell swoop. That is unless you are the owner of arguably the best pitcher in the game and are looking to unload him. The Toronto Blue Jays have been handed a golden opportunity to infuse elite prospects into their farm system or get young, major-league-ready talent directly onto their roster by pulling the trigger and dealing Roy Halladay.

There's a very harsh reality for the Blue Jays to deal with right now. Their pipeline of young players, aside from the recent emergence of the likes of Aaron Hill and Adam Lind, has been unimpressive. So, what they should expect or ask to get in return for their ace pitcher?

At this stage, the Yankees, to no one's surprise, look like they could be a major player for the Jays' hurler. Fortunately for Toronto, New York also has the pieces to put together a very enticing package. History tells us that more often than not the sellers of these big-name pitchers end up receiving far less big-league-ready talent in return than is initially speculated, making it even more imperative for the Blue Jays to choose wisely.

Will they receive a package featuring Phil Hughes and Joba Chamblerlain from the Yankees? No, they will not and that's why they need to find one player to headline any potential deal. The risk of taking quantity over quality is tangible, and although we've yet to see the likes of Deolis Guerra as a finished product for Minnesota, the Twins settled for a package bereft of that one top-flight talent in the Johan Santana deal.

Carlos Gomez had his question marks and proved to be very raw offensively, and Kevin Mulvey and Phil Humber profiled as mid-rotation starters. We'll see how Guerra pans out, and his upside is good, but Toronto cannot make the same mistake of relying on low-level players or players with limited upside in a blockbuster deal.

About the only other trade in recent memory in which there's a precedent related to Halladay is the CC Sabathia deal in 2008. That deal was centered around prospect Matt LaPorta, a player the Indians had been very high on since his days as an amateur. The complimentary pieces in the deal like Zach Jackson have not panned out, but Cleveland still has a player in LaPorta that they feel has star potential. And, there in lies the art of a blockbuster trading. The Blue Jays need to be certain of getting a star-caliber prospect rather than a package of less thrilling players.

With that in mind, Toronto will have a handful of names that would have to be included in any deal for Halladay. From the Yankees, they should receive one of Phil Hughes, Austin Jackson, or Jesus Montero. From the Red Sox, their short list should include Clay Buchholz, Daniel Bard and possibly Casey Kelly. For now, let's think about just what kind of package from the Yankees it would take to land Halladay.

Given their hesitancy to go the extra mile for Johan Santana, the Jays shouldn't expect to land two of the group of Phil Hughes, Austin Jackson and Jesus Montero. Don't expect Joba Chamberlain to be paired in any deal with the aforementioned names either. So, the decision Toronto would need to make is which one of these names can have the biggest singular impact on the organization's future.

The Blue Jays have been more successful in developing hitters in recent years than they have with pitchers, so despite the upside of Jackson and Montero, their focus should be on Phil Hughes. You can say it was because he was working out of the bullpen, but Hughes found a comfort level in 2009 that we hadn't yet seen from him as a big-leaguer. The curveball was sharper, the aggressive demeanor he had shown in the minors returned, and his velocity was better. Hughes is now a stronger, more confident pitcher still possessing the stuff to be a frontline starter. Toronto will have trouble finding this kind of young, high-upside arm that has already been broken in on the major league level.

The next question is what if the Yankees balk at the idea of dealing Hughes? Joba Chamberlain would probably be the next name to come up. You can say what you want about the Chamberlain starter-vs.-reliever debate, but given his skill-set this isn't a pitcher who figures to improve on what he currently is as the years go by. Some pitchers rely on stuff, others on pitching aptitude and command, while a select few are the total package.

There's a good reason that Chamberlain shows flashes of brilliance but rarely maintains it for long stretches. When he has his good stuff, especially out of the bullpen, he has two above-average pitches, including a 7 slider on the 2-8 scouting scale. The problem is when things aren't going his way and his high-effort delivery gets out of sync. Therein lies the difference between him and Hughes. Hughes has shown the ability to change his strategy, make adjustments and rely purely on command at times.

Very few times in 2009 did we see the type of fastball command from Chamberlain that Hughes can often display. The moral of the story here is, when evaluating young pitchers, you are better off taking the pitcher who has more than one gear and has shown a learning curve over his time in the majors. Chamberlain's raw stuff grades out better than Hughes' but can you really point to many improvements that Chamberlain has made since arriving in the big leagues?

He made attempts to mix his other pitches as a starter in 2009, but when push came to shove he remained a two-pitch pitcher that relied heavily on simply having his good stuff that day. And, all excuses aside, there's no hiding that his stuff even upon returning to the bullpen wasn't the same as when he initially burst onto the scene in 2007. The velocity was consistently down and we saw far fewer hard, disappearing sliders.

If you're the Yankees, Chamberlain is the young arm you part with, not Hughes, if a deal is put on the table for Halladay. Of course, if you are the Blue Jays you have to hope you can pry Hughes away.

Toronto then has the task of building a deal around someone like Hughes that works for both them and the Yankees. They would likely seek a lower-level pitching talent along the lines of Manny Banuelos, D.J. Mitchell, Jeremy Bleich, or Hector Noesi.

The Yankees would have to also include one of their better position prospects not named Montero or Jackson. And, the overall feeling among scouts is that the next name on that list is Austin Romine, the Yankees' lesser known but highly talented right-handed catching prospect. Romine showed good raw power this year, and has the above-average defensive tools that Montero lacks.

Given the Blue Jays' scouting philosophy, pitchers Ian Kennedy and Alfredo Aceves also figure to be arms they will ask the Yankees about. Kennedy in particular could be a wild card given how good his stuff looked in the Arizona Fall League. Let's not forget how skilled a pitcher he showed the potential to be before his health issues. He has the command and pitchability Toronto has been well known to put an emphasis on in their scouting department.

Receiving a package that includes two or more of New York's prized commodities is a pipe dream for the Jays if the recent history of trades involving star pitchers is any indication. With that said, it's incumbent upon Toronto's front office to get a young arm that not only can contribute in the present but for years to come. The Yankees have the personnel to give them what they want, and the depth in their farm system to be flexible in any negotiations. We could find out in a hurry just how highly both the Yankees and Blue Jays value Hughes and Chamberlain.

But, if presented with a choice, choose wisely Toronto, and choose Phil Hughes.

Frankie Piliere spent the last three seasons working as a scout, most recently in the professional scouting department for the Texas Rangers in 2009. He now serves as the National Baseball Analyst here at FanHouse.