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For a long time now I’ve had this worry: what if everyone in the front offices of baseball’s 30 teams started getting it? I mean not so much how to make the right moves, but how to avoid the ones that are so obviously wrong.

When that day came, I worried, professional wiseasses such as myself would be hard-pressed to cast stones at anyone in print. We would be turned out in the street, left to eke out a living in some unglamorous capacity where wiseassery is not a prerequisite.

The funny thing is, though, my fears continue to be unfounded. The day on which teams stop making foolish choices that drain revenue and return very little in production does not appear imminent. In spite of huge advances in assessment tools, there are teams, and specifically general managers, who continue to squander untold sums on doomed relationships with unworthy ballast hirelings.

Given the events of the last week, those of us in Wiseasses Local Number 14 are safe for now. For instance, there’s a middle infielder who didn’t become a regular until he was 27 years old. In his first full season, he logged an EqA of .256, then didn’t match that figure for six years. Finally, at the age of 34, he revisits the heights of his prime and manages a .265 EqA. Which in this sequence suggests a norm: the years scraping by below replacement level, or the half-way decent, late-career splurge?

If you’re the Yankees considering Tony Womack, it’s the latter.

What is interesting about the Womack signing is that the man the Yanks took a pass on in order to make room for the recent Cardinal had a better EqA in 2004. Not only that, but Miguel Cairo has a better career EqA (.249 to .244) and is four years younger. One could argue that normal free-agent rules don’t really apply to the Yankees, that the $4 million they’ll be giving Womack over the next two years is essentially nothing in the grand Yankee scheme. There is at least this to consider: when Womack reverts to form, New York can certainly afford to discard him and bring in a brand-name second baseman without having to worry about double-billing at one position.

Here’s a question I think every general manager needs to ask during free-agent season:

If this player weren’t available, would I want him?

What the hell do I mean by that? I am asking GMs to consider the possibility that a given player is only desirable because he just happens to be out there for the taking. Here’s another way to look at it: if he were under contract to another team, who would you be willing to trade to get him? Make a list. If the list doesn’t contain anybody decent from your organization, then maybe you’re doing the wrong thing or, at the very least, offering too much money.

I honestly believe that free-agent season causes some teams to throw the big shekels at a guy they wouldn’t normally even inquire about if a trade were involved. Does the fact that a player doesn’t cost live personnel in return make him more desirable? When you think about it, the opposite should be true.

Free-agent signings are the one-car accidents of baseball. With a trade, there is someone else involved and assigning blame is a little more complicated. Maybe the other general manager has hypnotic powers or is a slick-talking huckster who plays the unsuspecting GM for a rube. It could happen to anyone. A free-agent signing, though, is your idea. Yes, an agent can call and propose a deal, but any GM that’s worth his salt isn’t going to listen to agents when it comes to building his roster. He already knows who is and who isn’t a good fit for the team.

The Womack signing is not the only Yankee freak-out of the week. A good number of unfinished pyramids were also funneled down Jaret Wright‘s chimney. A case could be made that Wright never had a good season until 2004, his eighth year in the majors. Here’s some more free advice for general managers: don’t reward a player with a contract that’s longer than their track record. In other words, one good season should be worth a one-year contract. Two years (consecutively) should be worth two and three years, three. Is that so much to ask from a free agent? (Now, don’t take this too literally. It doesn’t mean you give a seven-year contract to a 37-year old who’s had seven good years in a row.)

It must be a little disconcerting to the Yankee fan intelligentsia (no, that’s not an oxymoron) to see their normally with-it team pulling the trigger on some very questionable deals. Yankee free-agent screw-ups really don’t matter, though. As with Womack, they’ll just print more money and give it to the guy they have to bring in to pick up Wright’s slack. One can’t help but wonder if the Yankee Age of Reason is drawing to a close, though. Are these two signings an indication that a team that clearly “gets it” is becoming one that doesn’t?

If so, that’s good news for professional wiseasses everywhere.