Roy Halladay has the headlines right now. Every major national outlet features a story about him on their MLB page. SI.com even has an homage to Halladay titled “The Race for Roy.” We’ve written about him just a few times over the last two weeks. When the best pitcher in baseball hits the trade market, he’s bound to capture our attention for a while. Eventually, though, the Halladay trade rumors will die down. Next up on the list of players connected to the Yankees could be John Lackey.

Though he’s taken a backseat to Halladay so far this off-season, Lackey is the best starting pitcher on the market. There are others with as much talent — Rich Harden, Erik Bedard, and Ben Sheets at their best can be as good, even better than Lackey, but they’re not as sure a bet as Lackey. Even tough he’s missed time the past two seasons, he’s still managed to pitch over 160 innings in each. Good innings, too. Even in a depressed free agent market he’ll get paid.

By not offering arbitration to any of their free agents, the Yankees have, like last winter, kept free the most possible payroll. This might have been a move related to the individual players — i.e., they thought that there was a good chance the player would accept and they didn’t want to pay the player an amount determined by an arbiter. But it might be that they want available payroll so they can replace one of their departing free agents with a new, younger player. Lackey makes plenty of sense in this regard. Adding him to the Yankees rotation could solidify it for 2010 and beyond.

If the Yankees do seek Lackey’s services, they’ll face plenty of competition. The rumors might be light now, but at the right price the Red Sox, Phillies, Mariners, Rangers, Brewers, and of course the Angels could be interested. It’s tough to say how high any of them will go, but it’s a good bet that, if they’re interested, the Yankees would be near the top of that pack. As they showed with A.J. Burnett last winter, they don’t like being outbid.

Jon Heyman talked up the Yanks’ interest in Lackey a month ago.¹ “Word is that the Yankees probably will be willing to repeat A.J. Burnett’s $82.5 million, five-year contract for Lackey,” he wrote. Whose word that is I don’t know, but it sounds reasonable enough. Lackey’s stuff might not be as imposing as Burnett’s, but he’s generally been healthier, has comparable ERAs, and has better control than Burnett. If this were two years ago, Lackey might see $100 million. But in this market, I’ll buy that a five-year, ~$80 million deal is the best he’ll do.

Assuming they structure a potential deal the same as Burnett’s, the 2010 payroll would be $186.8 million, plus arbitration raises to Melky Cabrera, Brian Bruney, Chad Gaudin, and maybe Sergio Mitre, plus a left fielder and a DH, plus possibly Andy Pettitte, plus roughly half a million dollars for every other player to fill out the roster. In other words, if the Yankees are truly interested in Lackey, they’ll have to commit to a higher payroll in 2010, something they’ve hinted isn’t likely. Not only that, but as we’ve discussed, it would mean a commitment to keep payroll above $200 million for most of Lackey’s deal.

Lackey’s most obvious destination remains the Angels. They have only $77 million committed to 2010 payroll, though they do owe first-year arbitration raises to six players, including Erick Aybar, Jered Weaver, and Joe Saunders. Even so, their rotation would be severely weakened without Lackey. Since they stand to lose the most, I think they’ll make a serious run to bring him back. If they can spend $18.5 million per season on Torii Hunter, they can do something similar for John Lackey.

When the off-season began, I didn’t think the Yankees would be too serious about Lackey. He’s the best free agent pitcher, sure, but with the Yankees payroll commitments and the risky nature of giving pitchers long-term contracts — and especially after doing it twice last off-season — I didn’t think the Yankees would do it again. After they declined to offer arbitration to any of their free agents, though, I’m beginning to wonder. Lackey would cost them only money, rather than money and prospects, and he would fit in perfectly behind A.J. Burnett in the rotation.

I wouldn’t count on the Yankees signing John Lackey. They have plenty already committed to the 2010 payroll and still have a few holes to fill. But I wouldn’t be surprised to see them make a serious run, nor would I be disappointed if they signed him. Paying your top three pitchers almost $60 million per season isn’t ideal, but if they’re quality pitchers and the team is winning, I doubt they’ll mind much.

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¹And Lackey isn’t even a Boras client. (Up)

Following the 2007 season, the Yankees needed pitching. They’d just been eliminated from the playoffs because their ace, Chien-Ming Wang, failed twice to hold down the Cleveland Indians. While Wang was still one of the league’s better pitcher, the Yankees needed more. Not only was Wang questionable as an ace, but the pitchers behind him were all questionable as well.

Mike Mussina had been removed from the rotation at the beginning of September because he’d pitched so horribly. Roger Clemens was a goner after his body couldn’t handle the rigors of a half season. Phil Hughes and Ian Kennedy, though impressive at times in 2007, were still risky rookies. Joba Chamberlain, because of innings concerns, would likely start the year in the bullpen. The only constant behind Wang was Andy Pettitte, and even then it wasn’t clear until later in November that he’d return.

The Yankees could have used a free agent pitcher that off-season, even a No. 2 starter type. Yet none existed. The top starting pitchers on the market were Pettitte, Curt Schilling, Greg Maddux, Carlos Silva, and Kyle Lohse. The Yanks would get the best of those, but what remained wouldn’t help much. The Yanks were better off seeing what they could get from their rookies. It was a pretty clear call to pass on this free agency class.

Yet there was still one option. The Minnesota Twins dangled Johan Santana, the best pitcher in the league at the time. It would cost the Yankees at least one of their young starters, Hughes, but that would replace uncertainty with something a bit more reliable. With Santana atop the rotation, the Yankees would have a formidable 1-2 punch. This is why the pro-Johan crowd was so disappointed in the 2008 Yankees. With an ace they might have weathered the competition and made the playoffs.

The Yankees didn’t jump on Santana for a few reasons. First was the allocation of resources. The Yankees would have to use their player resources to trade for Santana, and then use their financial resources to sign him to a long-term deal. That’s quite a commitment, even for a pitcher like Santana. The second reason was that the Yankees looked ahead to the next free agent class and saw that if they held back on Santana, they could reap the rewards a year later.

We all know the story from there. The Yankees used only their financial resources (and, technically, potential player resources by surrendering draft picks) to sign CC Sabathia and A.J. Burnett. Pretty smart, eh? The Yankees exercised foresight in the winter of 2007-2008, and it paid off in time for the 2009 season. They face a similar situation this winter. John Lackey is the top available free agent starter, and he’d slot in well as the No. 3 man in the Yanks rotation.

I think it’s time again for the Yankees to exercise foresight. Lackey is a nice pitcher, sure, known to most fans as a workhorse. Despite the reputation, he’s missed a decent amount of time in the last two seasons, including the beginning of the 2009 campaign with elbow issues. He wouldn’t be a terrible signing, but he’d be another long-term, high-money contract added to the books after the Yankees added three in 2008 and renewed three in 2007.

If the Yankees hold back on Lackey this off-season, they could again reap the benefits of a deep free agent pitching class in 2010-2011. Highlighting the potential free agents are Josh Beckett, Matt Cain (late edit: damn team options), Roy Halladay, Cliff Lee, and Brandon Webb. There’s no guarantee that any of them reach free agency, but there are five names there compared to the one this off-season. Not to mention, I’d rather have three of them than Lackey, and the other two are still strong alternatives at worst (though there is the issue of Webb’s shoulder).

Adding John Lackey to an already strong starting rotation would certainly help the Yankees chances in 2010. With Pettitte and then one of Chamberlain and Hughes at the back end of the rotation, they’d almost surely have the best in the game. That’s enticing, but I think waiting is the best option here. The Yankees have a slew of back-end starter candidates, including a number of young players who they’d probably like to evaluate. That way, when they get to the 2010-2011 off-season, they’ll have a better idea of whether they’d really like to pursue a free agent starter, or if they’re comfortable where they are.