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Heyman: Yankees ‘have a real reason to believe’ they can land Halladay

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Over the past three winters we’ve seen big name starting pitchers on the trade block. The Twins made clear their intentions to trade Johan Santana in the winter of 2007-2008. Last year, Jake Peavy dominated headlines for months, as the Padres fruitlessly dangled him in November. This year it’s Roy Halladay. Unsurprisingly, the Yankees have been connected to each player. They passed on both Santana and Peavy, but could it be different this year? SI’s Jon Heyman seems to think so.

What has changed between July, when the Yankees didn’t make a serious run at the available Halladay, and now? The Blue Jays’ general manager situation. They’ve since fired J.P. Ricciardi and have replaced him with Alex Anthopoulos. Learning from his predecessor’s mistakes, Anthopoulos has a different stance on Halladay than Ricciardi. The latter was hesitant to trade Halladay within the division, and also would not grant a trade partner a window to negotiate an extension. As we learned this morning, a Anthopoulos could allow an extension window. In his column this morning, Heyman notes that Anthopoulos will be more willing to deal within the AL East. Says the Jays’ GM:

“This isn’t the NBA where you’re talking about one of five guys on the floor at all times … If you have two trades that are identical, and one is in the division and one is outside, then it’s easy to go outside the division. However, if the trade is better inside the division, I think you have to take a look at it. We have to do what’s best for our organization.”

Another factor that has changed is Halladay’s price tag. As Heyman notes, the Red Sox made a large offer for Halladay in July, consisting of Clay Buchholz, Justin Masterson, Michael Bowden, and Nick Hagadone. From the Yankees, Heyman reminds us that the Blue Jays wanted a package centering around both Joba Chamberlain and Phil Hughes. The Blue Jays won’t get anything close to that this winter. They still should trade Halladay, but will have to accept a lesser package of prospects. That will make him more attractive to both the Yankees and the Red Sox.

Still, I’m not sure the Yankees will be serious players in this sweepstakes. They have their top two pitchers locked up for four and six more years, and they also have a number of promising young arms to complement them. Adding Halladay would be a good move for any team, but considering the price they’d have to pay, they might opt to stick with their guys and wait to see if Halladay reaches free agency next winter. I say this because even though Anthopoulos will deal more openly than Ricciardi, the Yankees have shown that they’re not keen on paying twice for a player.

Anthopoulos’s willingness to deal within the division will clearly open an avenue for the Yanks. All things equal he’d deal Halladay elsewhere, but if the Yankees have the superior offer he’s not going to spurn them. That means, however, that the Yankees would have to top any offer from another team, and the other team in question probably needs Halladay more than the Yankees. Unless the market is truly limited to just the Yankees, Mets, and Red Sox (which I doubt), it stands to reason that another team would be willing to offer more for a player they need, and who would be a luxury for the Yankees.

The negotiation window also makes Halladay more attractive, though I’m not sure it’s a tipping point for the Yankees. Heyman talked to a GM who thought that Halladay could get a “Santana or Sabathia deal.” Halladay will be 33 early in the 2010 season, so I’m not sure any team will be willing to offer him a six-year extension, especially if it comes at $23 million per season. Maybe the Yankees would be willing to offer a four-year, $92 million extension (so they’d have him for five years), but again, that would mean paying a bounty in prospects and then doling out $23 million per season. That just doesn’t seem to fit the team’s M.O.

No one can rule out the Yankees acquiring Roy Halladay. He’s clearly available, and the Yankees have already been connected to him. Given the team’s past behavior, though, I doubt they get too far in negotiations with the Blue Jays. They seem more apt to make a deal for John Lackey, who will just cost money, or to take a chance on a high upside player like Ben Sheets. That’s the way Brian Cashman has operated, and unless something drastic changes in the Halladay situation, I think he’ll pitch 2010 elsewhere.

Rumor du jour: An extension window for Halladay

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As a follow-up to yesterday’s discussion on Roy Halladay, Jordian Bastian of MLB.com throws a wrench into the plans. According to Bastian’s sources, the Blue Jays are willing to allow a negotiating window for any team interested in acquiring Halladay. The Blue Jays’ ace has just one year left on his contract, and a negotiating window would allow Toronto to extract more value for Halladay. As iYankees notes, this move is a similar to the one the Twins employed in the Santana trade talks, and I’m not surprised to hear it. After all, as I said yesterday, the Blue Jays need to land a big impact player if the team trades Halladay, and a negotiating window gives them more leverage.

In other rumor news, Tyler Kepner runs down the potential organizational wishlist for the Hot Stove league. He doesn’t cover much new ground, but the summary is a succinct one of the Yanks’ desires for an outfielder, a starting pitcher and a few younger players. A team of mid-to-late 30s players can only carry a franchise so far.

Drilling down on Roy Halladay

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When it comes to pitchers on the block, the Yankees are always a likely destination simply because, for the last 15 years, landing pitchers has been the team’s modus operandi. They acquired David Cone in 1995, David Wells after the 1996 season and Roger Clemens prior to 1999 campaign. In the 2000s, the names — Javier Vazquez, Randy Johnson — kept coming but with less success, and just a year ago, the Yankees nabbed CC Sabathia and A.J. Burnett out of the clutches of free agency.

So we arrive in the winter of 2009-2010 with Roy Halladay seemingly filling the role Johan Santana played in 2007-2008. Already, the Yankees have been rumored to be interested in Roy Halladay, and the new Blue Jays’ GM Alex Anthopoulos seems both willing to ship off Halladay and willing to send him to an AL East competitor.

The parallels to Santana are obvious. Halladay is one of the American League’s top five pitchers, and as he has aged, he’s become a smarter and better pitcher. Over the last two years, he’s 37-21 with a 2.78 ERA and 414 strike outs in 485 innings. He has thrown a whopping 18 complete games over the last two years. As a comparison, the Yankees’ entire pitching staffs have thrown just four complete games in that same span.

Similar to Santana, Halladay is playing out the last year of his contract, and the Blue Jays are unlikely to resign him after 2010. Furthermore, as the Twins were in 2007, the Blue Jays are living through their first off-season under a new General Manager. While Bill Smith inherited a healthy organization, Anthopoulos has his work cut out for him as he tries to compete with the big guns of the East while uncoupled Toronto from a few bad contracts.

So what, then, would a potential trade partner expect the Blue Jays to want, at least initially? For Anthopoulus, trading Halladay will be a defining moment of this off-season. He’ll be trading one of the best pitchers to throw in Toronto and big crowd favorite at a time when the team is hurting for attendance. He’ll need to recoup that investment while stocking up for the future. In that sense, I don’t see him settling for a package as weak as the one Minnesota received for Santana.

If I were a betting man, I’d guess that Anthopoulus would initially ask for Jesus Montero. At that point, Brian Cashman would hang up the phone. But the point remains: Toronto will need an impact, near-can’t miss prospect to give up Halladay right now. Since the Doc has but one year left on his contract, a team acquiring him may have to give up just one prospect, but it will be a costly one. Would Austin Jackson get the job done? Would the Yankees feel comfortable trading him? Does Toronto, as many others do, feel Jackson’s stock is low right now?

In writing about John Lackey last week, Joe mentioned how Halladay is a desired piece potentially available next winter. That, of course, is where the Yanks found themselves with Santana, but Johan never hit free agency. Brian Cashman will have to ask himself if he wants Halladay enough to pay in prospects and later in cash or if the team is willing to chance it and wait. Josh Beckett and Cliff Lee loom large in 2011 as well.

Right now, this is sheer speculation and the framework for a discussion on Halladay. The rumor mill is quiet in advance of the Winter Meetings, and teams are waiting to see how the market shakes down. When the Hot Stove warms up, Halladay will be front and center. Let’s see how the Yanks approach a big-name pitcher this time around.

Rumor du Jour: Roy Halladay

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That Jon Heyman, he just loves tying every big-name pitcher to the Yanks. Today’s rumor of the day from Heyman suggests that the Yanks will inquire about Roy Halladay. The Blue Jays’ was infamously not traded this past July, and that non-move was the straw that broke the proverbial camel’s back as J.P. Ricciardi was fired by season’s end. Unless Halladay can be gotten for cheap, the Yanks probably won’t acquire him for the same reason the team didn’t trade for Johan Santana: Halladay will be a free agent after 2010, and the team will not pay for him in both prospects and cash. The career Blue Jay turns 33 in May.

Halladay leaving Toronto would be good news for Yanks

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The Blue Jays started the 2009 season as hot as can be. On May 12 they were 23-12, a game up on the Red Sox in the AL East and 6.5 ahead of the Yankees. While some thought they were for real, it looked more to me like a 2005 Orioles job. Lo and behold, almost two months later they’re 43-41, seven back of the Red Sox and six back of the Yanks. They’re not out of it, but it would take an incredible run to charge back in this powerhouse AL East.

What does this mean for the Jays? Ken Rosenthal thinks it means they’re ready to take offers for ace Roy Halladay. It’s not the first time we’ve heard Halladay speculation, but with a year and a half left on his deal the Jays will never find a bigger haul for him than they will this month. General Manager J.P. Ricciardi has said that the team’s best chance to win next year is with Halladay in the rotation, and that’s true. But is it their best long-term option?

What further complicates the situation is that the Jays owe gobs of money to Vernon Wells and Alex Rios, who are both underperforming, through 2014. The Jays just have to hope they produce, because there is little or no chance of trading either without eating a significant portion of the contract. Moving Halladay, who rightly would be the highest-paid Jay next year, could improve the team not only with prospects, but with a bit of financial flexibility that they could use to make another deal in the off-season.

There are almost no bad scenarios for the Yankees here. Rosenthal’s list contains only three American League teams: the Yanks themselves, the Red Sox, and the White Sox. Obviously, the Yanks don’t want to see Halladay starting at Fenway any time soon, but almost any other scenario, including acquiring him themselves, looks just fine.

What about acquiring him? Rosenthal notes that Ricciardi would deal within the division, though we all know there’s a premium there. Any package would probably have to start with Phil Hughes, and then include one of the Yanks’ precious few bats, likely one of the catchers. Would Hughes, Romine, and a third prospect, probably of the top-10 variety, be enough to land Halladay? Would the Yankees be wise to make such a move?

There’s no doubt that acquiring Halladay would leave the Yankees with the best rotation in baseball. In the short term, they’d be as well off as any other team, probably better off. In the long term they’d be giving up prospects, sure, but prospects can bust. It looks like Phil Hughes is finding his way, and it would probably suck to face him four or five times a year. But it wouldn’t be nearly as bad as facing Halladay that many times.

Chances are, Halladay stays put. Teams are more reluctant to part with prospects than ever, especially because of their economic value. The Blue Jays will request a ransom for Halladay, and rightly so, but other teams might not be so keen to part with young, cheap, controllable players to acquire an expensive one whose contract runs only through 2010. If there’s a deal to be made, though, I expect the Yanks will at least kick the tires.