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Pettitte's Yanks redux nearly thwarted

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Ken Rosenthal

Ken Rosenthal has been the FOXSports.com's Senior MLB Writer since August 2005. He appears weekly on MLB on FOX, FOX Sports Radio and MLB Network. He's a member of the Baseball Writers Association of America. Follow him on Twitter.

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Judging from the difficult, protracted talks between the New York Yankees and left-hander Andy Pettitte, it’s reasonable to wonder how Pettitte might react if his comeback sputters.

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Pettitte stunned the baseball world Friday by agreeing to a one-year, $2.5 million minor-league contract with the Yankees. But the discussions, which began in late December, were full of stops and starts, right to the very end.

At first, sources say, Pettitte was unsure of whether he even wanted to return. Later, he was uncomfortable with the money the Yankees offered - their early proposals were for less than $2.5 million. He also was uncomfortable with the team’s insistence that he pitch in the minors, a point on which Pettitte eventually relented.

As the negotiations accelerated, the two sides explored a number of different financial proposals, including a personal-services contract that would not have been considered guaranteed money for the purposes of baseball’s luxury tax, major-league sources said.

One person with knowledge of the talks said that Pettitte was uncomfortable with the concept and at one point was ready to end negotiations with the Yankees and possibly even consider other clubs.

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Other sources said it was the Yankees who backed off the personal-services contract, believing that such an arrangement attached to a one-year deal would be viewed as a way of circumventing the tax.

Both Los Angeles Angels first baseman Albert Pujols and Washington Nationals third baseman Ryan Zimmerman agreed to personal-services deals worth $10 million in their recent long-term contracts. But Pujols signed for $240 million, Zimmerman $100 million.

If Pettitte signed, say, a one-year, $1 million deal with a $10 million personal-services contract, “it wouldn’t have passed any test,” according to one source.

The Yankees, though, are indeed mindful of the luxury tax — their payroll is $205.025 million, according to Cot’s Baseball Contracts, and they will be taxed 40 percent on every dollar over the $178 million threshold.

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In the end, though, the discussion of the personal-services deal proved just one element of the negotiations. The bigger issue by far is whether Pettitte will be realistic about his comeback.

Honesty is one of his most admired traits. But star athletes at the ends of careers often are the last to believe that they no longer are good enough.

Pettitte was so excited about his offseason workouts, he wanted to pitch in the majors immediately, sources said. But the Yankees were reluctant to make such a commitment, and not simply because they already had six starters for five spots. Their bigger concern was that Pettitte, who turns 40 on June 15, had not pitched in 17 months.

According to one source, here is how the talks unfolded:

Pettitte first signaled that he might attempt a comeback when one of his representatives alerted Yankees general manager Brian Cashman to the possibility during the winter meetings in early December. Pettitte and Cashman then spoke later that month.

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Cashman told Pettitte that if he returned, the Yankees would be willing to pay him the same salary he earned in 2010, $11.75 million. But Pettitte wasn’t certain he wanted to pitch at that point, saying he first wanted to work out for six weeks. Cashman told him that the Yankees couldn’t wait; they needed to upgrade their rotation and had other moves in the works.

On Jan. 13, Cashman swung into action, acquiring right-hander Michael Pineda in a trade with the Seattle Mariners and reaching agreement with free-agent righty Hiroki Kuroda on a one-year, $10 million contract. Cashman called Pettitte to inform him of the news, and told the pitcher that he could “shut it down,” stop working out.

In late February, Pettitte joined the Yankees in spring training as a guest instructor. He met with Cashman at the end of his brief stint and said again that he wanted to return. He had shut it down for only seven to 10 days. He was throwing again and felt great. Could they work something out?

Cashman wasn’t sure — he had no payroll flexibility, no opening in his rotation. Yankees ownership, in fact, had vetoed a potential deal with free agent Mike Gonzalez, a left-handed reliever, around that time. But for Pettitte, a member of five World Series champions with the Yankees, they were willing to make an exception. And talks resumed.

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In the end, the two sides struck a deal, providing baseball with a surprising feel-good story at a relatively quiet point of spring training. Still, the Yankees know they are paying Pettitte far less than his performance might merit; they did not even give him incentives.

Pettitte wants to pitch. The Yankees want to win. The two sides again might live happily ever after, but the negotiations were anything but smooth.

No one should be surprised if Pettitte’s comeback is bumpy, too.

Tagged: Angels, Yankees, Nationals

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