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CC Sabathia has every reason to void the remaining four years and $92 million on his contract. While that’s the most money any player will have ever left on the table, there is a 100 percent chance he’ll exceed that total, in both years and dollars, on the open market. But that won’t stop the Yankees from trying to prevent his impending free agency.

According to a New York Post report, the Yankees are currently preparing an offer, or a series of offers, intended to retain Sabathia before his opt-out date arrives. Their idea consists of a five- or six-year deal with a raise over Sabathia’s current $23 million annual salary. That sounds like a reasonable offer, and there’s definitely a chance Sabathia could accept.

Chances are the six-year offer is the only one that gets it done. Six years at $24 million per season totals $144 million, which exceeds the offer the Yankees made for Cliff Lee last offseason. That’s fair, given how much Sabathia has contributed to the Yankees in the last three years. They can even bump that up to $145 million, thereby exceeding Lee’s record $24 million annual salary. A five-year deal would certainly have to come in at around $125 million, and would include at least one option.

The Yankees stand to learn plenty with such lucrative offers. If Sabathia accepts, then he was true to his word about enjoying New York and his declarations of, “I’m not going anywhere.” If he declines a six-year deal worth $140 to $145 million, then the Yankees have to question Sabathia’s intentions. Again, $145 million over six years would give Sabathia the highest average annual value of any pitcher contract in history, to go along with his highest gross total of $161 million. Should he decline such an offer, he’s signaling that he would consider an offer from another team that, in all likelihood, wouldn’t constitute much more than a marginal increase over the Yankees’ offer.

Even so, a six-year offer to a 31-year-old pitcher might seem like a lot. But consider that 1) the Yankees made a six-year offer to Lee last off-season, 2) there is no pitcher on the market who matches Sabathia’s abilities, and 3) Sabathia’s importance to the team’s success the past three seasons. For instance, he has averaged 34 starts and 235 innings per season with the Yankees. In the three years before Sabathia arrived the Yankees had six pitchers reach 200 innings, but none eclipsed 218 in any season. Also, none had an ERA within 15 points of Sabathia’s average 3.18 ERA. That is, he’s been a consistently top-notch workhorse. That’s the type of pitcher the Yankees can pay a premium for.

Without Sabathia in 2012, the Yankees would be in quite a bind. They’d absolutely have to go after C.J. Wilson, and Wilson simply isn’t as good as Sabathia. Even when you factor in the contract Wilson would require, Sabathia seems like the better value. The Yankees recognize this, and will prepare an offer that appears difficult to refuse. If you truly liked pitching somewhere and they offered you a six-year deal that paid you more per year than any pitcher in history, wouldn’t you take it?

(AP Photo/Kathy Willens)

Barring something completely unforeseen, CC Sabathia will opt out of his contract with the Yankees a few days after the end of the World Series. That doesn’t mean he hates New York or anything like that, it’s just a smart business move on his part. We’d all do the same thing. The Yankees will undoubtedly try to re-sign their ace, though the intensity of their pursuit and the number of other teams that get involved remains to be seen.

Contracts for elite players like Sabathia are difficult to predict because there are so few comparables out there. Sabathia already holds the record for the largest contract ever given to a pitcher, but it’s tough to see him topping the original seven-year, $161M deal he signed prior to the 2009. I see four points of reference for Sabathia’s new contract, at least four “major” points of reference. Let’s recap…

Four-years, $92M

This is what is left on Sabathia’s current contract, the money he is leaving on the table by opting out. Obviously he and his agent believe they can find more than this on the open market (assuming they opt out), and they’re almost certainly right. In a perfect world, CC would just not opt-out and stick around under the terms of his usual agreement, the right amount of years and dollars from the team’s perspective.

Five-years, $120M

When Cliff Lee spurned the Yankees and went back to Philadelphia, this is the guaranteed contract he took from the Phillies. There’s a vesting option for a sixth year, but we’re only concerned about guaranteed dollars at this point in time. Options and buyouts can be manipulated to do anything. I figure the negotiations for Sabathia’s new contract start here, since he’s still younger than Lee was last winter and has a much longer track record of success and durability.

Six-years, $132M

According to Jerry Crasnick, this was the Yankees’ final offer to Lee last winter. Again, this is guaranteed money only. If they were willing to go that far for a guy that hadn’t done anything for them, shouldn’t they be willing to do at least that for a comparable pitcher that’s already helped them win a World Series? I’m sure Sabathia and his agent will play that card, I know I would.

Seven-years, $161M

As I said earlier, this is contract Sabathia is already working under, the largest ever for a pitcher. I can’t imagine he’ll get this many years or this many dollars this time around, but stranger things have happened.

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These are just reference points for Sabathia’s next deal, I’m not saying he’ll get exactly that amount for exactly that many years. I’d love love love if he’d take the five-year, $120M package, but I suspect it’ll end up being closer to the six-year, $132M deal. That’s not based on anything, just a hunch. Who knows, maybe he’ll surprise everyone and stick around. I wouldn’t hold my breath though. Anyway, a post like this is screaming for a poll, so let’s do it.

It’s only a matter of time (about two weeks) before CC Sabathia exercises his opt-out clause in search of greener pastures. There’s been some speculation that the Yankees would approach their ace about a new deal before he uses the opt-out, but agent Brian Peters told Buster Olney (Insider req’d) that no such talks have taken place between the two sides yet…

For now, Sabathia’s focus is entirely on remaining with the Yankees, according to his agent, Brian Peters. “CC has been clear about how he feels about New York and the Yankees,” Peters said on Saturday morning, “and we will exhaust all of our efforts to reach a new agreement (with the Yankees).”

Asked if the negotiations had started, Peters said, “As of today, I’ve got nothing new to report.”

Olney also mentioned that some in the organization are concerned about how/if Sabathia’s weight affected him towards the end of the season, which is completely reasonable. You also have to worry about his weight with regards to his right knee, which required surgery to repair a slightly torn meniscus last offseason as well as five years ago.

The other day we heard that the Rangers are going to throw a boatload of cash at Sabathia, and chances are they won’t be the only team willing to spend on one of the game’s few legitimate left-handed aces. Every big market club will be connected to CC at some point this offseason, even if their only intention is to drive up the price for everyone else. Peters indicated that the two sides have yet to discuss a new deal, but once Brian Cashman‘s situation is wrapped up, I think it would be rather prudent of the Yankees to start talks as soon as possible.