Halladay trade talk likely to top winter meetings bill; more notes

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Roy Halladay is coming off another fine season in which he went 17-10 in 32 starts with a 2.79 ERA. Chuck Solomon/SI

Star Blue Jays pitcher Roy Halladay, who hopes his current residence in trade limbo will be resolved within the next couple of months, will be pleased to hear that the Jays have engaged the Yankees in at least initial trade talks. According to sources, Toronto officials mentioned at least four Yankees players and minor leaguers that interested them when the teams spoke recently: Phil Hughes, Joba Chamberlain, catching prospect Jesus Montero and outfield prospect Austin Jackson.

Executives with multiple teams who have spoken to the Blue Jays characterize trade talks thus far as "preliminary" and say they expect discussions to heat up at the winter meetings that begin next Monday in Indianapolis. Halladay has told Toronto he is considering spring training the deadline.

The Yankees, Red Sox, Phillies, Mets and Angels are all seen as having interest and varying degrees of ability to make a deal for the superstar pitcher. While the Blue Jays are controlling the action now, Halladay has a big say in where he goes, thanks to a full no-trade clause in a Blue Jays contract that was signed with a hometown discount. With that in mind, people who know Halladay say he is sure to approve at least the Yankees, Red Sox and Phillies, based on his three major criteria:

1. A team that perennially wins.

2. A team that trains in Florida, preferably on the west coast of Florida, near his Oldsmar home

3. A team that perennially wins. (Yup, it's that important.)

With those objectives in mind, the Yankees, Red Sox and Phillies look like the best fits. The Angels qualify under Nos. 1 and 3 but miss on No. 2, while the Mets may have an issue with 1 and 3. The one team Halladay was known to be cool toward last summer was the Texas Rangers, who train in Arizona.

But, every potential deal will be judged on a "case-by-case basis," Halladay's agent Greg Landry said by phone. So that means no one should be counted out yet.

The Jays' interest in Hughes, Chamberlain, Montero and Jackson (to clarify, they didn't say they'd insist on all four) didn't shock the Yankees, since they heard similar requests from Toronto when the Jays were shopping Halladay last summer. But the difference this time is that the Yankees and their rival Red Sox are considered serious suitors, as new Blue Jays GM Alex Anthopoulos wisely has made clear he isn't about to eliminate Toronto's intradivisional rivals -- who also happen to be baseball's two richest teams -- from the bidding war that's expected for baseball's most durable pitcher and arguably its best one, too. Halladay has finished in the top five in Cy Young voting the past four years, has thrown at least 200 innings in all four of those years, and incredibly, he has nearly three times the number of complete games over the past three seasons (25 to nine) than the next most durable pitcher.

Halladay is expected to be the talk of Indy in a year when the trade market is interesting but the free-agent market is weaker than usual, at least at the top. Halladay is a unique modern-day star who appears to have way more interest in winning than money, which makes him even more appealing. "You've got to meet this guy," one Blue Jays person said.

Nonetheless, competing GMs seem to believe there's a decent chance he'll seek a mega-extension even though the topic doesn't appear to have even been raised as yet with prospective teams. If he wants, Halladay, who is to make $16 million in 2010, could probably get a five-year extension for $23 million minimum per year, which is the yearly salary paid to Johan Santana and CC Sabathia. "He'd be crazy not to (insist on an extension). What if he gets hurt? He'd be dead," one GM said.

If an extension is part of the equation, that even makes it more of a Yankees-Red Sox game, as those are two teams that could afford the paycheck. One competing GM questioned whether the Angels would want to pay such an extension (though they quietly offered Sabathia at least $100 million over five years). The Mets already are paying one pitcher $23 million and have a multitude of other needs, and it would be a tight squeeze for the Phillies, as well.

Meanwhile, the Yankees had a boffo year financially (though they won't say how boffo), and their biggest need is for another starting pitcher. The Red Sox are baseball's second-biggest money maker and are also showing interest in a frontline starting pitcher, though their biggest need may be for a run producer, particularly with Jason Bay as yet unsigned.

So it's no surprise some baseball people are starting to see a Yankees-Red Sox competition coming here. A Yankees person suggested he suspected the reason it came out recently that he'd accept the Yankees could be because the Jays are "trying to get Boston's attention." Meanwhile, a Boston person said, "Toronto's trying to get a Yankee-Red Sox thing going here." The Jays are believed to be interested in at least a couple Red Sox youngsters: pitcher Clay Buchholz and superlative infield/pitching prospect Casey Kelly, who seems to be rising on everyone's wish list. "He has a chance to be special as a pitcher," one AL scout said said of Kelly. Though it's possible the Jays see him as a third baseman. The left side of their infield seems of particular interest to Toronto brass.

The Phillies can't be ruled out, either, although budget restrictions and other interests (like getting Cliff Lee extended) may complicate any possible pursuit by them. There seems to be a lot less buzz regarding Halladay around the Phillies than the Yankees and Red Sox, and GM Ruben Amaro has said their priorities are to fill their third-base hole (Mark DeRosa, Placido Polanco, Adrian Beltre, Miguel Tejada, Chone Figgins and Mike Lowell have all been considered) and to shore up their bullpen. The Phillies want to keep their payroll around $140 million, which would make it a very tight squeeze. One way to find a little money to pay Halladay's $16 million 2010 salary might be to consider a swap of Cole Hamels, whose bright star has dimmed a tad this year.

In any case, Halladay will be anxiously awaiting. He is said to have been bitterly disappointed to have waited through last year's talks only to stay put. That's why he doesn't want talks to drag into this spring or season. He and the Jays have made such a great team to this point, and he doesn't want anything spoiling that.

"It was such a distraction last year, not only for him but his teammates. That's something we want to avoid," Landry said. "There was so much hoopla. It didn't do anybody any good."

The smart money says the Jays get the deal done this time around, and they do it with one of their archrivals.