The case against Lackey came two years ago

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.