What's Derek Jeter worth to the Yanks?

NEW YORK -- In September 2009, flashes lit up a soaking wet Yankee Stadium when Derek Jeter poked a single to right for hit No. 2,722 of his career, passing Lou Gehrig on the franchise's all-time list.

Jeter's teammates spilled out of the dugout to first base to congratulate him. The gigantic video board in center flashed images of Babe Ruth and Gehrig, the men Jeter had passed as the Yankees' all-time hit king.

The crowd chanted, "Der-ek, Jet-er! Der-ek, Jet-er! Der-ek, Jet-er!"

It was a night pulled out of a Yankeeography and singed in the memory of any baseball fan who witnessed it.

It was a perfect moment that could be financially capitalized on by the New York Yankees' merchandising arm at Steiner Sports Gifts & Collectibles. But Jeter isn't one to sit in a room and sign until his hand hurts.

"Around individual accomplishments, he is very low-key," Brandon Steiner, president of Steiner Sports, said before making a statement of fact, not one of complaint. "He didn't sign as much as we could have sold."

Jeter has been so beloved by fans, teammates and opposing players because of how he handles events like that memorable night in September, 2009. He is understated and appropriate when the spotlight is on him, which makes him very likeable as the face of the big, bad Yankees. But how much is that worth? And will the Yankees be able to capitalize on it?

The team is running a "business" so negotiations could become "messy" -- those were Yankees owner Hal Steinbrenner's words -- for a players whose "value cannot be overstated" -- Jeter's agent, Casey Close, has stated. The two sides have started their game of chicken with Jeter able to negotiate with any team beginning at midnight Saturday when he becomes a free agent for the first time in his career, which means the Yankees have exclusive negotiating rights until then.

The classic Jeter dilemma is screaming as loud as the 4-train to 161st Street, and making its way to national headlines. Jeter has an intangible value to the Yankees, but the Yankees have that same value for him. They are each better off married than divorced.

"He is the brand," said St. Louis Blues interim CEO Mike McCarthy, who ran MSG Network when it owned the rights to Yankees' games.

From McCarthy's unique position as a top television executive and now as part of an ownership group in St. Louis, the 36-year-old Jeter adds premium value to the Yankees and YES -- both estimated to be worth more than a billion each, maybe much more -- as he likely becomes the first Yankee with 3,000 hits.

"If he does it in a Minnesota Twins uniform, the whole thing is half, if not less," McCarthy said.

The Yankees, McCarthy said, will make extra money by selling out the almost always full Yankee Stadium and with higher TV ratings. No one can say how much more money exactly.

"Front offices and fan bases get very attached to players and think they could never do without them, 99 out of 100 times that turns out not to be the case," McCarthy said. "Players come and go, it feels like you will never survive the attachment to a certain athlete and then a fill-in comes along and life goes on.

"Then you have a different category, which would be the 'Derek Jeter Category,' where you can't even picture the team without him or him in another uniform. It's akin to putting the Rolling Stones together without Mick Jagger. You can't do it.

"Even after the sponsorship impact, he goes beyond the metrics. He is the brand."

That is why most everyone thinks that the two sides will meet eventually. Beyond the fact that GM Brian Cashman considers Jeter the team's best option at shortstop for next season, Jeter is the face of the franchise.

Jeter is everything the Yankees try to stand for. He is a champion with a clean public persona. Jeter is the one who closed out the old Yankee Stadium with just the right words, and he is the one who had the foresight to insist on having a recording of legendary PA announcer Bob Sheppard always introduce him. He is tied to the Yankees like no other baseball player is connected to his current team.

But Jeter didn't get to the top without being ultracompetitive, which shows itself in the boardroom as much as on the field.

To Jeter's right on the infield, Alex Rodriguez -- who has embarrassed the "brand" with his steroid admittance and sorted controversy -- sits with a contract that takes him to 2017, a 10-year agreement that could leave A-Rod with $300 million by the end of it.

As the face of the organization, this is not lost on Jeter, who very well might want a deal that takes him until he is 42, as well. With dreams of owning a baseball team, this is Jeter's last chance for a huge score as a player.

If Jeter weren't Jeter, he might be worth somewhere in the three-year, $30 million range. He will receive a premium, of course, but the argument is did he already get paid for helping to build YES and the new stadium with his just-completed 10-year, $189 million contract or do the Yankees still owe him for what he has done, and not for what he might do?

Marc Ganis, president of Sports Corp Limited, points out the Yankees took a great risk with the last deal. Jeter lived up to the contract, but if he had gotten hurt or underperformed he still would have been paid. Ganis, who has done work with the Yankees in the past, said there is a uniqueness to the Jeter-Yankee relationship.

"He has tremendous value, but it is very hard to quantify," Ganis said. "It is almost impossible to do. He is worth more to the Yankees than any other team. The Yankees are worth more to him in endorsements than any other team."

But it isn't an A+B=C kind of thing for either side. Jeter, according to Ganis, has millions of dollars worth of endorsements from Gatorade, Jordan Brand, Gillette and Ford. If Jeter stays with the Yankees, Ganis envisions Jeter's commercial brand lasting the rest of his life.

"He becomes the Arnold Palmer of baseball," Ganis said comparing Jeter and Palmer's endorsement prowess. "He provides a direct link to the great Yankees past and its future."

McCarthy, who spent more than two decades at MSG, said the TV ratings will go up when Jeter approaches 3,000 hits. The Yankees usually lead the majors in attendance, but they will likely have sellouts as long as Jeter goes for the record.

"It is going to be such a magical event that people will tell their grandchildren that they were around," McCarthy said.

With 2,926 hits, the event will likely happen next season. On that night, the Yankees' and Jeter's brands will grow stronger as he becomes the team's first player with 3,000 hits. Jeter will likely handle it with understated class and not a lot of signatures. It will add another magical night to the Yankees' history, but nobody knows what it'll be worth financially.

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

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