Never chase your money.

It’s an age-old gambling adage, meaning don’t keep betting when your only goal is to get back what you’ve already lost.

It’s an urge that gamblers at any level must fight and it can be very difficult to resist.

This is how otherwise sane-thinking fathers and uncles end up with broken knee caps and orbital sockets; this is how little Suzie loses a college fund and ends up a lady of the night.

In the world of professional baseball, general managers should be reminded that the “never chase your money” philosophy applies to them as well.

I was thinking about that earlier today when I saw a report about Zack Greinke and his supposed willingness to come to the Yankees. The Royals right-hander is just one year removed from winning the Cy Young award and there have been persistent whispers that he could be moved in a trade this winter.

In case you haven’t noticed, this is an unusually thin year in terms of starting pitching on the open market. It appears that Cliff Lee has better timing than Sal Swatch and Chaz Rolex combined.

Want some more perspective? The general consensus next best option on the market is none other than Carl Pavano, a man who once missed most of a season with a bruised ass.

Obviously, the Yankees would rather rent out their private suites to Ron Jeremy’s production company before giving the American Idle another dollar, so it makes sense that Greinke would pique their interest if they failed to acquire Lee.

But that’s when Brian Cashman should remember: Never chase your money.

I’m sure Greinke is a nice person, but let’s not forget he also left baseball for a time because of some serious anxiety issues. This is the same guy who didn’t even want to have a press conference after he won the Cy Young award.

He appears to enjoy the cameras and bright lights as much as an exposed pederast on an episode of To Catch A Predator.

Bringing him to New York would probably be the most obvious set up for disaster since the last time Javier Vazquez was chucking 83-mph fastballs at the Stadium.

Speaking of Vazquez, here’s to hoping Cashman learned some lessons about chasing the money last winter: Vazquez was a Plan B after Derek Lowe signed with the Braves. Nick Johnson was a Plan B after Johnny Damon chose to sign with the Tigers.

Are we seeing a pattern here?

Greinke would be an even more tempting Plan B because of his obvious skill-set and age, as he just turned 27. But the red flags flapping in the wind simply can’t be ignored.

Ideally, Lee and his beautiful, sweet wife buy the Yankees’ sales pitch and he’ll be endorsing outrageous paychecks for the next six years. But if the courtship fails, the organization must be disciplined enough not to make a panic move that sets the club back even further.


Dan Hanzus writes the Yankees blog River & Sunset and can be reached at Follow Dan on Twitter @danhanzus.

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