According to Joel Sherman of the New York Post, the Yankees were hoping they could come to a quick agreement with some of their free agents, however that no longer seems to be the case.
#Yankees hoped familiarity/liking being with NYY would helpquick deals with Headley/McCarthy, but now they don't see that happening (cont)— Joel Sherman (@Joelsherman1) November 5, 2014
The Yankees have already started contract talked with Chase Headley and were believed to prefer Brandon McCarthy over some of the more expensive free agent pitchers this year.
The strategy of getting Headley and McCarthy to sign quickly before the market can properly shape their value is a smart move. However, it's also smart of the players not to sign any time soon. By waiting for the bigger names to come off the boards first, Headley and McCarthy will be able to see their value on the market rise as better options become limited. So unless the Yankees give them an overpriced deal, they're not going to settle with the Yankees just because they happened to like playing in New York. I just hope the team isn't surprised by this.
It's likely that Chase Headley will wait to sign until Pablo Sandoval has been taken off the market. Headley could then make a killing as an alternative for the teams who missed out on the top third baseman in the free agent class. After the half-season Brandon McCarthy had with the Yankees, teams are going to see the right-hander as a less expensive alternative to names like Jon Lester and Max Scherzer. Organizations that miss out on certifiable aces like those two are going to want to pay a little extra if McCarthy is the best pitcher around.
The Yankees can try to lock these guys up earlier, but it would be in the players' best interest to wait for their true markets to form. Hopefully by that point the Yankees will still be able to retain them, but they aren't signing now for anything under top dollar. You can't blame the Yankees for trying, unless they legitimately thought it could work. Then we'd be in trouble.