Pettitte's departure major blow

The Yankees should have known better than anyone the earnestness of Andy Pettitte, who wants nothing more than the simplest of lives. When he pitches, Pettitte wants the catcher to do the heavy mental lifting for him: You put down the signs, I'll make the pitch.

He's happiest when he's around his wife and children, and when he travels away from them, he desperately misses them, sometimes to the point of distraction. Pettitte's next lie will probably be his first. He does not care about being the highest-paid, the most recognized, and setting records is not important to him. He is virtually incapable of manipulation.

The Yankees did try to work out a deal with him over the last six weeks, but now Pettitte is gone, having agreed to a three-year deal with the Houston Astros.

According to a baseball source, the Yankees offered Pettitte a three-year, $30 million deal shortly after the World Series, telling Pettitte this was just an opener, and that the team was ready to offer more. Pettitte's agents countered with a three-year concept: $51 million, with enough deferred money to take down the real average annual value to $15 million. The agents then informed the Yankees that Pettitte wanted to try free agency, and with that, Yankees' executives decided to back off in good faith to honor Pettitte's request.

A Yankees' official says the team did check in repeatedly with Pettitte's representatives, nudging them to move things along -- and when they did not get a response, they made the trade for Javier Vazquez, out of a growing concern that Pettitte ultimately would sign with Houston, to be closer to home.

Finally, as Pettitte neared a deal with the Astros on Wednesday, the Yankees offered a three-year, $39 million contract, about $7.5 million more than the Houston deal. The agents countered with a four-year, $52 million request, and told the Yankees that even if they agreed to those terms, Pettitte might still sign with the Astros; Pettitte was getting pressure from within his family to stay at home.

The Yankees tried, but only after letting the whole process drag out for too long -- they could've made their move early this year, in the spring -- and only after the professionalism and camaraderie that were the hallmarks began seeping out of their clubhouse.

For perhaps only the second time since 1918, the Yankees face a serious pitching deficit in their rivalry with the Boston Red Sox. If a seven-game playoff started today, the Red Sox would roll out Curt Schilling, Derek Lowe, Pedro Martinez and Tim Wakefield. The Yankees: Mike Mussina, Vazquez, Kevin Brown and Jose Contreras.

Not long after losing Pettitte, Yankees owner George Steinbrenner reacted and made another move. The Yanks have tentatively acquired Brown from the Dodgers for Jeff Weaver, a deal that makes sense for both teams, because if healthy, Brown can be overpowering; he'd be great in the postseason, if the Yankees could keep him together until then.

But the loss of Pettitte will be a huge broadside blow to the Yankees' chances of actually making it into the playoffs, something they've done in every season since 1995. Boston will probably be the divisional favorite going into next year, and Toronto is a very dangerous team for the Yankees, young and hungry, two qualities that might have escaped the Yankees for the foreseeable future.

Pettitte's departure also is another indication of the overwhelming dysfunction that looms on the horizon for the Yankees. Manager Joe Torre -- who argued to prevent the Yankees from trading Pettitte to Philadelphia in 1999, and argued again this offseason for the Yankees to aggressively re-sign the left-hander -- goes into next year as a lame duck manager.

He has indicated he does not want to talk about another extension, and it's easy to envision an early season slump leading to his dismissal, a last chance for Steinbrenner to humiliate Torre on the way out; that's what Steinbrenner does.

Torre could go at some point, in an era when Steinbrenner is increasingly pursuing players like Raul Mondesi and Gary Sheffield. The Yankees' players thought last season was a whacky, contentious ride; well, they ain't seen nothing yet.

There could have only been one or two compelling reasons for the Yankees to conduct the negotiations with Pettitte as they did. He has had elbow trouble in the recent seasons, pitching through pain; the Yankees know better than any team the condition of his elbow ligaments.

They also know that before Roger Clemens arrived in 1999, Pettitte would never be confused with a workaholic. His conditioning wavered, and in 1998 and '99, Pettitte struggled, before tagging along for Clemens' manic workouts. Pettitte's body hardened and he improved, but perhaps the Yankees suspect that with Clemens now retired, the motor that drove Pettitte in recent seasons is gone. Pettitte is 31 years old, and he's stated, quite honestly, that he cannot imagine sustaining the desire to pitch anywhere near as long as Clemens did. He will have to push himself.

But the Yankees thought enough of Pettitte to make the three-year, $30 million offer to him shortly after the World Series. What they probably could have done, at some point, was to make the decision easy for him, last spring or last summer, to signal clearly to him.

But Pettitte became a free agent and started thinking about other stuff. Like how great it would be to be with his family year-round, playing in a park a short drive from his home. Like how crazy the Yankees' culture will become, once Torre and pitching coach Mel Stottlemyre are gone. Like how different the team is now than it was during their recent glory years.

And by the time the Yankees tried to make a last-ditch offer, they had, in fact, helped made the decision easy for him.

Buster Olney is a senior writer for ESPN The Magazine.