When will The Conversation begin?

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The Conversation is almost inevitable. The Yankees will ask Derek Jeter his thoughts about changing positions. It really isn't a question of if it will one day take place, it is more when does The Conversation happen, and how do you broach the subject with the most legendary Yankee since Mickey Mantle.

That means The Conversation could happen as soon as this offseason, when the soon-to-be 36-year-old Jeter's 10-year, $189 million contract expires.

"You have to have a conversation about a transition at some point," said former Mets GM Jim Duquette, who faced a similar circumstance with Mike Piazza's transition from catcher to first base in 2003. "You have to ask, 'When he is comfortable with that?'"

So, as defensive metrics are showing a steep and increasingly rapid decline in Jeter's glove skills, we aren't alone in wondering when, if ever, Jeter will be willing to move from shortstop? When a reporter broached The Conversation before a game last week in Minnesota, Jeter didn't want to talk much about it.

Reporter: Have you ever thought about playing another position?

“

The disagreement always comes about the timing of the move. I think it is part of the conversation when you are doing the contract.

” -- Former Mets GM Jim Duquette

Jeter: "Why would I?"

Reporter: Well, Ernie Banks, Robin Yount, Cal Ripken Jr. all switched from shortstop.

Jeter: "I'm not thinking about that."

Then, politely enough, Jeter asked for the interview to end, if moving positions was going to be the line of questioning.

The issue is the strongest dynamic at play in this, Jeter's walk year. It is almost impossible to imagine Jeter leaving the Yankees, but it is not implausible to envision him at another position, even if he says it hasn't crossed his mind.

The real questions for Jeter's upcoming negotiations are the amount of years he will get and the position he will play by the contract's expiration date. Will Jeter demand to have the length that Alex Rodriguez's contract has? A-Rod's deal takes him until he is 42.

One prominent agent thinks Jeter and the Yankees will likely come to a four-year, $20 million-plus per season agreement. That would keep Jeter as a Yankee until he is 40. Others feel the sides could work out some personal service contract that could make Jeter a Yankees employee for life.

But that's not the topic that will rage on the talk show lines over the next few years.

The Yankees have no vacancy signs on first, second and third. The outfield could be an option, but if they sign Carl Crawford this offseason, it eliminates left. With Curtis Granderson or Brett Gardner, center may not be available. Maybe Jeter simply DHs more, while continuing to be the No. 1 shortstop? Sure, that's a possibility, but recent stories and rumblings have harped on Jeter's range. The sabermetricians are out there, taunting Jeter with their numbers.

[+] Enlarge

Mark Cunningham/Getty ImagesDerek Jeter has made leaping throws a staple of his defensive arsenal throughout his career.

The statistics say Jeter is still going to his right fine, but in the early part of the season, he was having more trouble going to his left.

Remember the recent Sunday night Mets game, in which two balls to his left rolled under his glove? Those helped lower his plus-minus rating, according to Baseball Info Solutions (which looks at how often balls in play are turned into outs), to minus-7 on balls hit to the left of the typical shortstop's spot.

He's since improved that to minus-3, a slight drop from last season. Going left has been an issue for Jeter before -- one he's improved upon greatly after posting ratings of minus-25, minus-10 and minus-14 from 2005 to 2007. The early struggles this year again raised questions.

Scouts have seen it, too, but aren't as alarmed.

"He may not have the range he once had," said an National League advance scout. "He has very long arms that help his range that sometimes goes unnoticed. I don't know why people malign his defense."

The "How is Jeter's defense?" topic is so hot that Yankees general manager Brian Cashman won't even touch it.

"It turns out to be a no-win situation," Cashman said.

Cashman is right. Publicly, it serves the Yankees no value to rev up the debate. Privately, they need to have The Conversation with Jeter, if they feel he won't always be a shortstop.

"You owe it to a player to tell them what you see," said Mike Arbuckle, a Royals executive who has been in the game for three decades.

But Jeter is not just a player. He is the team's most popular player. He is The Captain. He is a future Hall of Famer with no stains on his reputation, despite playing in the steroid era. He is going to end up in Monument Park.

While the number crunchers say Jeter -- with more age -- will become a statue long before he has a monument, he's possibly the most respected player in the game. How he goes about his work and when he does it the best enters into The Conversation.

"You can't get the perfect player the whole time," an advance scout said. "He is the heart and soul of that team."

Cashman has had a conversation with Jeter about his defense before. Cashman challenged Jeter to improve his range. After enlisting trainer Jason Riley to make Jeter quicker to his left, the question of Jeter's defense had faded following a bounce-back 2009.

Still -- regardless of Cashman's and the Yankees' true feelings about Jeter's defense, if you are going to pay a player $20 million a year, doesn't a franchise have a right to protect itself? Doesn't it need, in the best interest of the organization, to have a plan in place in case Jeter -- at 38, 39 or 40 -- isn't the same defender down the road?

It is possible that Cashman has already broached the topic with Jeter, though there is no evidence of that. One thing that Cashman, like Jeter, doesn't want to have is a conversation about The Conversation.

"That is not a productive conversation to have with you or the public," Cashman said. "There is nothing beneficial."

Cashman added, "We intend to try and re-sign him back this offseason."

In 2003, when Duquette was the GM of the Mets, the team's front office wanted then-manager Art Howe to establish a relationship with Piazza. After meeting about it in the offseason, they decided that spring training would not be the right time for Piazza to work at first, because they felt it would cut into his preparation as a catcher.

During the season, however, in a situation baked with Mets controversy, and after years of the "Piazza to first" debate, Howe casually walked over to Piazza in the dugout and simply said, "We'd like you to take some ground balls at first."

It seemed inevitable that eventually Piazza would be asked to make the move. When Piazza was finally approached about it, he was prepared.

"Mike was great," said Duquette, who now hosts a talk show on XM Radio. "He didn't complain. He didn't balk."

The experiment to move Piazza -- who never said a cross word, but also never looked thrilled -- to first was a disaster. Piazza perhaps knew that his physical tools were not made for the infield. He was awkward at first and his distinguished Mets career ended somewhat clumsily.

The thing about great athletes, Duquette said, is what makes them excel also makes them the last to know. They have always been the best, and their expectations go unchanged even as their career expiration date approaches.

Jeter has always been a shortstop. The idea of running out to another position is as foreign a concept as asking him to settle for a B-level starlet.

"The disagreement always comes about the timing of the move," Duquette said. "I think it is part of the conversation when you are doing the contract."

Maybe they only lightly touch upon it, because there are some in the Yankees universe who think that Jeter may beat Father Time, despite the latter's undefeated record. Jeter, they will say, has a pretty good lifetime record on the diamond.

Last Wednesday in Minnesota, when Jeter cut short the interview about The Conversation, he demonstrated why this is such a compelling topic. Jeter seemed to give his real answers on the field, when the Yankees and Twins resumed a suspended scoreless game.

First, Jeter hit a go-ahead solo home run in the top half of the sixth inning. In the bottom half, there were men in scoring position and two out in a one-run game. The Twins' Delmon Young hit a hard grounder in the hole.

Jeter ranged to his right, backhanded the ball on the edge of the outfield grass and in his signature defensive move, jumped up and made a throw across the diamond to nail Young and save two runs and -- as it turned out -- the game.

It was as if Jeter were incredulously saying, "Have I thought about playing another position? Why would I?"

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

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Andrew Marchand

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Andrew Marchand is a senior writer for ESPNNewYork. He also regularly contributes to SportsCenter, Baseball Tonight, ESPNews, ESPN New York 98.7 FM and ESPN Radio. He joined ESPN in 2007 after nine years at the New York Post. Follow Andrew on Twitter »