As Mike noted earlier today, the Yankees Brain Trust has assembled in Tampa to begin preparing for next week’s Winter Meetings. One name bound to come up — as it has numerous times this week — is Roy Halladay. The Blue Jays want to trade him, and the Yankees have the pieces to acquire him.

As Halladay’s name has been the most talked-about this Hot Stove League, we have a general sense of what the Blue Jays want from a potential trade partner. Since the team has to replace one of its most beloved players who also happens to be a high-impact player, Toronto wants a Major League-ready arm and a top hitting prospect. Yankee fans have filled in the gaps for this to mean Joba Chamberlain or Phil Hughes along with Jesus Montero or Austin Jackson. That’s not an unreasonable expectation for Toronto’s initial demand.

When or if a trade goes down, Toronto’s price will come down, and with Halladay’s desire to see this wrapped up before Spring Training, the Yanks can wait out the Blue Jays. It’s beginning to look like The Son of Johan Santana. But not quite, as Buster Olney writes today.

In one of his better blog posts in recent months, Olney challenges the Yankees to be perfectly honest with themselves. We know that they publicly say Joba Chamberlain and Phil Hughes are both starters with high ceilings, but after a few years of watching the pair develop, Olney wants the baseball experts in the organization to lay it on the line. I quote at length:

But here are a couple of things that are different since the Santana talks: Hughes and Chamberlain. They are two years older, two years further along, with (generally) two more years of major league service time. Both players will be eligible for salary arbitration for the first time after next season. Hughes, 23, is coming off a year in which he demonstrated that he could be a shut-down reliever during the regular season — he struck out 96 in 86 innings, with a 3.04 ERA — before he struggled in October. Chamberlain, 24, had flashes of excellence as a starter, but generally was erratic, before finishing his year with some strong outings in the postseason.

If I were sitting in Brian Cashman’s chair, I would identify the smartest pitching people I have on my staff, whether it be manager Joe Girardi or pitching coach Dave Eiland or others, and I would ask them two questions: What are Hughes and Chamberlain now, and what do you think they will be going into the future?

In other words, do you think in three years they will be middle relievers? Do you think they will be dominant closers? Do you think they will settle in as back-of-the-rotation starters, or do you think they will be frontline AL East starters?

And if the smart people that Cashman trusts believe that Hughes and/or Chamberlain will be anything other than (A) dominant closers, or (B) No. 2-type AL East starters, well, then I’d call Toronto immediately and be ready to talk about trading one or perhaps even both of the young pitchers.

Olney is spot on right here. For three years, we’ve been touting the Big Three and the youth movement, but at some point, the Yankees have to recognize when to cash in some of their chips. I don’t know if Roy Halladay is the right move to make; I don’t know if now is the right time. After all, we can’t consider Joba or Phil disappointments, let alone busts, until years have gone by, and it’s very challenging to predict the baseball future.

But if the Yankees’ experts — if the men and women assembled in Tampa — are not sold on a stellar future for either of these young players, the time to make a move is nigh. As pitchers go, they don’t come much better than Roy Halladay, and the Yanks must ask, “What price an ace?”

One of the Yanks’ primary objections to any trade for Roy Halladay is the need to, in effect, pay twice to acquire the pitcher. The team will have to send some highly-touted prospects and a young Major League pitcher to the Blue Jays for the rights to Halladay, and then the Yanks would have to sign him to a long-term contract extension as the pitcher sits just one season away from a potential free agent payday.

We have, of course, been down this road before. In December 2007, the Yankees opted against acquiring Johan Santana because the team knew CC Sabathia would be available for just money after the 2008 season. This year, the team has been hesitant to leap into the Halladay fray because they know some top pitchers will hit free agency in both 2010 and 2011. Even if Doc is better and more durable than Santana, the Yankees aren’t going to change an approach that led to a World Series title.

But what if the Yankees only have to pay once for Halladay this year while gaining the opportunity to recoup some of the cost? Joel Sherman presents a one-year scenario in The Post today, and it goes a little something like this:

[O]ne faction of the Yankee front office has advocated trying to trade for Halladay, but not extend his pact. That way they would get Halladay on a very good contract for 2010 ($16 million) and then offer him arbitration after the season to secure two draft picks as a way to recoup some of the prospects given up in the trade.

According to Sherman, this idea is “not a strategy with much traction” within the Yankee Front Office, but I like the approach. It carries with it an idea that the Yankees would not have to give up as much to the Blue Jays if they aren’t requesting a negotiating window. It would simply be a player-for-prospects swap that would net the Yankees Roy Halladay’s age 33 season and the potential to pick up two first-round draft picks in the 2011 draft. With the Blue Jays are reportedly asking for a Major League-ready pitcher and an impact bat, the draft picks would definitely help offset the loss of young players.

Furthermore, Toronto could prefer this approach as well. What happens, for example, if the Blue Jays grant a team a negotiating window, but the team and Halladay can’t come to terms? Sherman, in a blog post, reported that Halladay is interested in Santana/Sabathia dollars, but Halladay will be five years older than those two were when they received their lucrative deals. It’s easy to see how a negotiating window could result in no trade.

There are, however, a few too many roadblocks for me to believe that a one-year rental would be a viable solution. First, the Blue Jays would have to feel that the Yankees’ offer remains the strongest even if other teams want the negotiating window. Perhaps, though, the other teams — assumed to be the Red Sox, Dodgers, Angels and Phillies — aren’t too keen on giving too many years and too much money for a 33-year-old pitcher. If no one wants a negotiating window, the Jays may not have that leverage. Right now, no one knows.

The other major problem is Roy Halladay’s full no-trade clause and his desire for some stability. With the no-trade clause, Halladay can veto any trade, and if a team is not willing to give him the dollars, he will simply reject the trade and file for free agency. Additionally, Halladay knows that the next deal he signs will be his last big contract, and he’ll want the stability and the guaranteed money up front. For pitchers, the end is just one arm injury away.

In the end, the idea of a one-year marriage with Roy Halladay is very appealing. It remains, however, a long-shot to come as the end to this saga. And so we wait for the Halladay sweepstakes to take shape.

In an unsurprising development, the Daily News reports that the Red Sox plan to aggressively pursue Roy Halladay early this off-season. According to the News’s source, the Sox want this done before the Winter Meetings. That puts pressure on the Yankees, who haven’t even determined their 2010 budget yet.

The Yankees do not want Halladay to land with their toughest division rival. With a rotation headed by Halladay, Jon Lester, and Josh Beckett, the Sox would have the best rotation in the AL, and probably in the majors. The Yankees have their top two set with CC Sabathia and A.J. Burnett, but even then they’d have to add a significant No. 3 to match the Sox’s prospective top pitchers. So what should the Yankees do in this situation?

Pursuing Halladay themselves makes sense. As with the Mark Teixeira sweepstakes, the Yankees could pull a huge swing, adding Halladay to their rotation and dubbing it the best in the game, while leaving the Red Sox in the dust. There’s a certain attractiveness to that plan, especially coming less than a year after it happened with Teixeira. The emotion of trumping the Red Sox, however, should not derail the Yankees long-term plans.

As in 2007, the Yankees face the issue of paying in both players and dollars for a front-line pitcher. There are certain situations where this makes sense. In others it doesn’t. The Yankees felt that paying such a bounty for Johan Santana wasn’t worth it at the time, and could feel the same way about Halladay now. He would cost them three or four prospects, plus a long-term extension, possibly in the $100 million range. Is that type of deal worth it for a 33-year old pitcher? Or is Halladay the exception, like Curt Schilling and Randy Johnson?

For the money, Halladay is probably worth it. He’s suffered minor injuries over the past few years, but has spent minimal time on the DL and has kept his innings counts among the highest in the league. In fact, Halladay spent two weeks on the DL in June of last season and still ended up with 239 innings, second most in the AL by one measly inning. His innings totals get so high because he finishes more games than any other starter — he’s led the league (or tied for the lead) in complete games for the past three seasons, and has led the league five times over his career.

The question facing the Yankees is of whether they want Halladay in their long-term plans. This is completely independent of any Red Sox rumors. True, Halladay on the Sox hurts the Yankees, but they can’t make long-term decisions based on their opponents. They have to figure out what players fit their plan, both in terms of the players themselves and the cost of acquiring them. If they feel that Halladay is an organizational fit and that the cost of acquiring him isn’t prohibitive, they should make a move to cut off the Red Sox. If they feel they can achieve the same effect with other pitchers, then they should bow out, even if it means the Sox landing Halladay.

If the Yankees decided to pursue Halladay, I think they have the pieces to top a Red Sox offer. In the Daily News report, Mark Feinsand and Bill Madden speculate that the cost for the Sox will start with starter Clay Buchholz and likely include 2008 draftee Casey Kelly. That’s certainly a strong start to a package, but as the report says, the Red Sox could be loathe to trade him. A Yankees offer of Joba Chamberlain plus Jesus Montero would likely top that. Whether the Yankees are willing to surrender such prospects, however, is a different story. Those are two players with excellent potential.

Based on the above speculation, I think that the Yankees are in an advantageous position regarding Halladay. They have the players to attract Toronto, and I think that unless the Red Sox grossly overpay, the Yankees can top them in most reasonable scenarios. The Red Sox are probably using this aggressive tactic to catch the Yankees flat-footed, putting pressure on them to decide their plans, lest the Red Sox land Halladay without a fight.

It’s easy to say that the Yankees should trade prospects for Halladay, but in a game as complex as baseball, decisions are never that simple. A deal for Halladay would dramatically change the franchise. The Yankees would lose several young, promising players for a 33-year old, plus a likely $100 million contract commitment. If they think that Halladay gives them the best chance to win, in 2010 and beyond, they should pull the trigger. If they think that their young players are poised to contribute, they should back off. The only effect the Red Sox should have on this decision is the timing. Other than that, the Yankees need to make the decision based on their own needs and projections, and not based on blocking a rival.