Is Derek Jeter still a money player?

What is Derek Jeter really worth? If you put blinders to the mystique and aura, how much value is there for a 36-year-old free-agent shortstop who delivers a .270 average, 10 homers, 67 RBIs and solid but unspectacular defense?

"Twelve million dollars over two years, maybe $10 million over two," one former GM said. "But I think he'll probably get a lot more than that."

He will get a lot more than that, because he is the most storied member of the New York Yankees since Joe DiMaggio or Mickey Mantle (each of whom, it seems fitting to mention, had his share of contract disputes in the Bronx).

Jeter has all the rings, all the legendary moments and 3,000 hits on the horizon. So even now he may be looking for a raise, not a cut, from his 10-year, $189 million contract.

That is why these playoffs are important for Jeter, because while he is working on his second hand of rings, the size of his next deal will be influenced by what he does this October. The Yankees measure their success by the postseason, so Jeter could lessen the impact of the poorest regular season of his career.

"I think they will wait and see what he does in the playoffs," said a major league scout who has worked in front offices.

Many baseball people think Jeter's next deal with the Yankees will be in the neighborhood of $20 million a season for three or four years. If the Yankees offer anything close to that, they will almost certainly be bidding against themselves.

"It is the exception to the rule," the ex-GM said. "It is not a rational contract. He is Derek Jeter."

If the discussion of Jeter's next contract were rational, he'd be downsizing. Shortstops at his age don't usually receive huge deals, especially not coming off a career-worst offensive season.

The way executives and agents normally judge the market is by comparing free agents to players at the same position who have signed in recent years.

Since the 1990-91 offseason, the only shortstops 34 or older who received contracts of $5 million plus per year were Marco Scutaro (Red Sox: two years, $12.5 million) and Miguel Tejada (Orioles: one year, $5 million), according to ESPN Stats & Information.

Of the under-34 set, the Dodgers' Rafael Furcal received a three-year, $30 million deal. The Giants' Edgar Renteria got two years at $18.5 million, and the Red Sox gave Julio Lugo four years and $36 million. So the initial two years for $10-12 million from our former GM is actually not that unreasonable -- except that we're talking about Jeter.

The ex-GM admits that Jeter comes with a different set of circumstances than a typical player, but when asked to put a Yankees legend tax on an offer, he suggested the Yankees might go to three years and $30 million. Even that estimation could be about $30 million short.

None of the aforementioned shortstops were about to become the first Yankee to have 3,000 career hits or was the captain of the most storied franchise in sports. None of them had a frenemy to his right who is signed until 2017, which adds a little spice to upcoming talks.

A little more than decade ago, the Yankees could have had Jeter for $118.5 million for seven years, but George Steinbrenner, not wanting to set a precedent, nixed the deal.

A year later, A-Rod signed his historic $252 million contract with the Texas Rangers, allowing Jeter to escape any public backlash over his subsequent decade-long, $189 million deal.

Now Rodriguez has another outsized contract that will take him until he is 42. This 10-year deal could be worth more than $300 million and is set to end in 2017.

No matter how clutch Rodriguez was last season, it's hard to imagine the end of that contract not being a dud. The Yankees probably will not want to make that mistake again.

"For the Yankees, it is not as much about the money, but it is about the length," the scout said.

Jeter dreams of owning a team. To do that, one more humongous score would be very helpful. Plus, there is the pride of a future Hall of Famer. Despite his numbers, Jeter is likely to be a shark in negotiations.

Rodriguez and his then-agent, Scott Boras, took advantage of the inexperienced Hank Steinbrenner, who was temporarily at the helm of the Yankees in 2007. Now, it is Hank's brother, Hal, and GM Brian Cashman who are clearly in control of the organization. They have to define what Jeter is now at 36 and how much his legend is worth.

"More than likely it is the start of the decline, but he deserves the benefit of the doubt more than anyone," the ex-GM said.

The scout added, "It could be aberrational, or it could be he is going downhill. That is something that their scouts have to decide."

That is why this October, Jeter is playing for a bit more than a ring. He is trying to prove that he is not on the wrong side of the hill as he heads into a unique negotiation.

What he does in the next four weeks could determine how many more Octobers he plays as a Yankee. He has a chance once again to show he is a money player.

Andrew Marchand covers baseball for ESPNNewYork.com. You can follow him on Twitter.

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