Lusting for Clemens, Pettitte brings back old Yankee memories

Dreams of 2000 are dancing in the heads of Yankee fans.

Jon Heyman, sports columnist for Newsday, is the one to blame for these pipe dreams. In Monday’s column, Heyman wrote that the Yankees are trying to convince Roger Clemens to join them for the 2006 campaign.

If Clemens opts for retirement or another season in Astros, the Yankees are lusting after Andy Pettitte, a pitcher they never should have lost in the first place. According to Heyman, the Yankees recognize that Pettitte’s contract, like nearly every Astros contract these days, is heavily backloaded. The Astros owe Pettitte $10.5 million in 2006 and $17.5 million in 2006. If Houston falls out of contention, the Yankees would be more than willing to assume the financial risk to get Pettitte back in pinstripes.

At least, those are the plans, according to Heyman. But why not both of them? Hey, these are the Yankees we’re talkin’ about. They’re rolling in dough. They had Clemens and Pettitte a few years ago. Why can’t they have Pettitte, Clemens, Randy Johnson, and Mike Mussina all pitching together? It would be the geriatric pitching convention. But age aside, how would the Yankees’ finances hold up with Clemens or Pettitte or both on board?

Currently, according to the excellent Hardball Dollars site, the Yankees owe players a guaranteed $183.77 million in 2006. That does not include the approximately $3 million Shawn Chacon will make or the league minimum doled out to Robinson Cano and Andy Phillips for their services this year. With those three included, the Yanks’ payroll will probably hit $187.5 million on Opening Day. Considering that the 2005 payroll was over $210 million, this is clearly a step in the right direction for the Bombers.

That is, unless they sign Clemens. Last year, Roger Clemens made $18 million, the most ever for a pitcher. And he earned every penny of it. He pitched to a 1.87 ERA and brought the Astros to their first World Series appearance. Despite his age, there’s little reason to believe that Clemens would regress too much. Were he to sign with the Yankees he would be pitching in the offensive-rich AL East instead of the fairly weak NL Central. He would have to face the Red Sox, Blue Jays, and Devil Rays. And he would probably cost the Yankees upwards of $15-18 million, bringing payroll closer to 2005′s astronomical figure.

With Clemens, the Yankees would become even more favored to win the AL title. But they would be spending more money than they wish. General Manager Brian Cashman has expressed a desire to build a leaner Yankee team, but the Bombers are clearly willing to make an exception if it means landing Roger Clemens for one last tour of duty. And, heck, the Yankees already are paying Clemens nearly $1 million in deferred salary in 2006. What’s a few more million?

Now, what if Clemens decides to retire? What if he signs with Houston but falls apart midway through the season? The Yankee fans, according to Heyman, will be rooting for the Astros to struggle because Andy Pettitte awaits on the horizon.

But Pettitte doesn’t really fit into Brian Cashman’s masterplan either. For 2006, the Yankees could easily take on Pettitte’s $10 million. In fact, I still can’t get over the fact that they let him go in the first place following the 2003 season. So if they got him back this year, it wouldn’t break the bank. The Yankees routinely pick up bulky contracts at the trade deadline. Sometimes it pays off (David Justice); sometimes it does not.

The problem is for 2007. The Yankees would owe Pettitte $17.5 million ($10 million in salary and $7.5 million in deferred payments). This would mean that the Yanks would owe ten players $123 million. They would be 15 players short of a full roster and already just a few million behind the next highest salary. It would hardly be financially prudent for the Yanks to paying so many players in their mid- to late-30s a lot of money.

Additionally, the Yankees would have to ship away a highly regarded prospect to land Pettitte. Even if the Yankees were willing to assume the salary, Pettitte wouldn’t come cheap, and the Astros know that. As the Yankees are interested in rebuilding a depleted farm system, the acquisition of Pettitte could throw a wrench into those plans.

So as Spring Training approaches and reporters look for stories, I can believe that the Yankees are interested in acquiring Roger Clemens, Andy Pettitte, or both. But when October rolls around, I certainly won’t be surprised if neither of them are pitching in the Bronx. These are just dreams from a long-gone dynasty.