I think Brian Cashman is doing the right thing by letting it be known he will be doing the calling this free agent season. As I mentioned earlier this week there is nothing wrong with letting the market develop. Ken Davidoff believes the way in which the Yankees and Red Sox do business makes it unlikely they will splurge on Roy Halladay, or any risky free agent signing. Rather, he believes they will focus their attention on bringing back some combination of Hideki Matsui, Andy Pettitte, and Johnny Damon. If the Yankees bring back two of their three free agents, and add a couple of complementary pieces, would the fans be happy? Better yet, are the Yankees maximizing the window of opportunity their aging lineup provides?

The Yankees lineup, according to OPS+, had 8 of 9 regulars significantly above league average. The only “below average” offensive player was Melky Cabrera and it was minimally below. I believe it’s unlikely this group can repeat 2009 collectively. Sure, you might get a better season out of A-Rod, but what are the odds of all nine offensive players performing at peak levels? To add another layer of complexity the Yankees farm system has some nice positional prospects, but none that appear to be everyday solutions. Austin Jackson, Kevin Russo, Ramiro Pena, and Francisco Cervelli may turn out to be solid big league starters at some point, but it’s not a guarantee in 2010.

It’s no secret that pitching is going to be so important. Maybe Hughes and Chamberlain are ready to step up and harness their potential. Even if they have their struggles you always have Sabathia every five days to right the ship. The problem is between Sabathia and the kids you have two question marks. A.J. Burnett is always going to be feast or famine. At this point in his career it would be foolish to think otherwise. Andy Pettitte eventually will have an expiration date and you better hope it’s not 2010. Realistically you have four question marks in the Yankees rotation.

Maybe Brian Cashman will look like a genius by passing on John Lackey and Roy Halladay. I find it ironic that these pitchers could be considered risky by the Yankees- the same team that handed out a five year deal to A.J. Burnett last winter. Line up Halladay, Lackey, and Burnett and ask ten baseball people which one is least likely to make it through a five year deal. I bet Burnett is the unanimous winner.

The Yankees have every right to be wary of this season’s market. On the other hand I wouldn’t get too confident. Remember, you won the World Series with three starting pitchers and two are far from a sure thing going forward. We have not seen a repeat winner since those Yankees teams of the late nineties. Those guys couldn’t hit like this bunch, but they sure had better pitching top to bottom. One other thing to remember: their offensive stars were in their early prime unlike this group. Would the fans be ok with the Yankees standing pat? I think the majority wouldn’t complain. Can the Yankees afford it? No.

Tags: Andy Pettitte, Brian Cashman, Hideki Matsui, John Lackey, Johnny Damon, Matt Holliday, New York Yankees, Roy Halladay