Last offseason, the Yankees were interested in Drew, but were told that he would only consider clubs that could offer him a job as a shortstop.
Boston was able to make that offer, and after signing with the Red Sox, Drew performed well enough to have earned a qualifying offer from the club this offseason. The one-year, $14.1 million deal would've been the highest salary of Drew's career, but he turned it down, choosing to join a shortstop-light free agent class with the hope of landing a long-term deal. Now, it appears as though his position has become something of a hangup for interested teams.
Boston has expressed interest in bringing him back, but it might have to be in a utility-type role.
Early on in their negotiations, Red Sox GM Ben Cherington let Drew and Boras know that the plans are for Xander Bogaerts to be the Boston shortstop, which might limit Drew to games at first, third and short against righthanded pitching.
The Yankees would like to sign Drew, but Derek Jeter is locked in as the everyday shortstop, even though he doesn't have as much range as he used to. Drew could fill in at second or third in New York, and spell Jeter at short or DH from time to time.
Drew might not start out the year at short in New York, but he's been a much better defender than Jeter over the last several years according to advanced fielding metrics. Drew can help his case for a new deal by being flexible, but the Yankees could probably help their case for another AL East pennant by asking Jeter to make a switch.