Boxed-in New York Yankees Lean On 'Win Now! Worry Later!' Strategy

The Yankees know full well that offering Cliff Lee a seven-year guaranteed contract is a bad idea. At least, I think they do.

Lee will turn 33 during the 2011 season. Signing him to a deal that would conceivably pay him over $20 million the year he turns 40 doesn't exactly reek of fiscal responsibility.

No, it doesn't approach the mind-numbing idiocy of Alex Rodriguez's contract. The foolishness of that deal—home run "milestone" escalators and all—will be remembered by historians the same way they recall Napoleon's decision to invade Russia in the dead of winter. Thanks Hank!

A better parallel may be Jason Giambi, another established veteran star the Yankees signed to a multi-year contract using the "Win now! Worry later!" strategy. Nearly 31 and having packed on roughly 80 pounds of muscle mass during the second Clinton administration, New York ignored the red flags and signed the Oakland MVP to a seven-year, $120 million deal nine years ago this Monday.

The Big G had his moments in pinstripes, but his PED non-admission admission combined with a steady decline in production made it a regrettable contract by its halfway point.

It's certainly conceivable the Yankees would feel the same way about Lee's deal.

For a more positive outlook, point to Mike Mussina, who began a six-year, $88.5 million deal with New York when he was 32, the same age Lee is now. Mussina never won a ring with the Yankees, but was more or less as good as advertised, even winning 20 games in his final season. He also drank Mountain Dew by the case and weirded out lughead teammates with his high intelligence, but that's neither here nor there.

And while past signings have produced mixed results, there's no disputing that the Yankees find themselves in a precarious position as things currently stand. Their biggest rival has turned the winter meetings into a personal playground, adding two (twenty-something) All-Stars in Adrian Gonzalez and Carl Crawford who stand to shift the balance of power in the American League.

There's no way to sugarcoat it—the Yankees need Lee just to keep up with Boston. Other than Crawford himself, no one benefited from the outfielder's mega-deal with Evil Empire (NESN Division) more than Lee did. It made the Yankees desperate, the exact scenario every blue-chip star dreams of when he reaches free agency.

To further complicate matters for the Yankees, the clock is ticking. Derek Jeter is 36. A-Rod is 35. Jorge Posada is 39. Mariano Rivera is 41. Andy Pettitte (assuming his return) is 38. A.J. Burnett will be 34.

The bill is coming due. Maybe not this year, maybe not the next, but there's an urgency to contend now before their high-priced veterans go from strengths to liabilities. The "Win now! Worry later!" roster makeup will eventually send New York into a rebuilding period of some kind. Signing Lee gives you the best shot for a title in your core's glaucoma golden years.

And if Lee doesn't sign with New York? Well, that's when Cash gets on the horn with Carl Pavano's people.

And that's when I donate my body to the Human Centipede doctor.

Dan Hanzus writes three columns a week on his New York Yankees site, River & Sunset. He can be reached at [e-mail]. Follow Dan on Twitter @danhanzus.