In Brian Cashman's search for pitching help, you would imagine that Justin Masterson would be the perfect target. They've been interested before, he's a ground ball pitcher, and he's about to hit free agency. Yet still, even counting all those reasons, the Yankees don't see Masterson as a solution to their rotation problem. At least not at the price it will cost them to acquire him.
This year Masterson has struggled mightily. He has a 5.51 ERA and 4.08 FIP on the season, however, despite his ability to keep the ball on the ground (58.5%) and prevent the home run (0.55 HR/9), he's struggled to keep the ball over the plate (5.14 BB/9 by far a career-worst). While they've already traded for a struggling pitcher in Brandon McCarthy, the Yankees must not see some major defect that they could correct, like a drop in velocity, for Masterson, and make him effective again.
That being said, much of Masterson's skill-set is very dependent on infield defense and the Indians actually have the worst-rated defense in baseball with -62 defensive runs saved. While we all know the Yankees don't have a very good infield, they would at least provide an upgrade with their -14 DRS. The Yankees undoubtedly have some kind of defensive metrics at their disposal and they're probably aware of how they compare to the Indians. The fact that they're still not interested must mean they really don't like what they're seeing from him, especially when it will take more than Vidal Nuno to get him.