Via Jon Heyman of Sports Illustrated:
Though he knew he wanted out of Kansas City, which has a promising future but looks like it will have a brutal present, [Zack Greinke] wasn’t sure where he wanted to be.
He told friends he didn’t think he could play in Boston or New York. But when he and Yankees general manager Brian Cashman met clandestinely in Orlando (Greinke’s hometown) at an off-site location during the winter meetings, Greinke’s desperation not to endure yet another losing season in Kansas City was such that he is said to have tried to convince Cashman that he wanted to come to New York. And that he could actually thrive in New York.
However, people who were briefed on that meeting said Cashman ultimately decided that Greinke’s first thought about New York was probably correct — that it wasn’t the best spot for him.
Greinke told people the day he accepted his Cy Young Award in New York City that he didn’t think he could ever live in New York, and kept telling friends the same. But as the days dwindled this winter, he made his surprise plea to Cashman to make him a Yankee.
It just speaks to how strongly the Yankees believe that the Bronx is the wrong place for Greinke. Consider that despite Greinke's lobbying, the Yankees—who have a strong need for starting pitching—still didn’t really make any push for a trade.
Greinke is a good pitcher too, but when a guy publicly says that he wouldn’t feel comfortable in a place, the tendency is to believe him.
Only when he felt more uncomfortable in Kansas City did he turn to the Yankees.
Part of me wonders what role his brother Luke Greinke played in this situation.
Luke was a Yankee draft-pick back in 2008. While pitching for the Staten Island Yankees, he told me that he wasn’t a big-city guy and felt uncomfortable not only pitching in New York City, but didn’t even like being there. I
t’s possible that the Yankees saw how Luke reacted and worried that Zack might feel the same way.
The Brewers look to have a good team this season, but Greinke won’t be a free agent until after the 2012 season.
If the Brewers are not contending next season if and when they lose some of their offensive punch in Prince Fielder (a free agent after this season), it is possible that Greinke could be back on the trade market before he hits free agency in two years.