Yankees Biggest Moves (and Misses) at the Winter Meetings

Mar 31, 2016; Tampa, FL, USA; New York Yankees relief pitcher Aroldis Chapman (54) smiles in the dugout against the St. Louis Cardinals at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-USA TODAY Sports
Mar 31, 2016; Tampa, FL, USA; New York Yankees relief pitcher Aroldis Chapman (54) smiles in the dugout against the St. Louis Cardinals at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-USA TODAY Sports /
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Dec 5, 2016; National Harbor, MD, USA; Los Angeles Dodgers pitcher Rich Hill (left) shakes hands with Dodgers manager Dave Rogers (right) at a press conference announcing Hill
Dec 5, 2016; National Harbor, MD, USA; Los Angeles Dodgers pitcher Rich Hill (left) shakes hands with Dodgers manager Dave Rogers (right) at a press conference announcing Hill /

Losing Rich Hill to the Los Angeles Dodgers

The New York Yankees were rumored to be one of four clubs in “full pursuit” of the best starting pitcher in the 2016-2017 free agent class, 36-year-old Rich Hill before he re-signed with the Dodgers on Monday for three years and $48 million.

While New York clearly could use an upgrade to their uncertain 2017 rotation, according to Jon Heyman of Today’s Knuckleball, the front office never made a formal offer to Hill. In retrospect, that may because the team was saving its limited payroll space for Aroldis Chapman, who was a safer bet to live up to his contract than Hill, even if the same level of upside wasn’t necessarily there.

After the Chapman and Holliday signings, Cashman told Andrew Marchand of ESPN that he was “tapped out of money for this winter.” It seems like the Yankees were only able to afford two of their top three free agent targets this winter, and ultimately probably took the safer route by putting that money into Chapman and Holliday.

Still, no available free agent had the ability to transform the potential of the 2017 Yankees like Hill, who presented the unique opportunity to acquire a front-of-the-rotation option for just money, on a short term deal. I had visions of Hill and Masahiro Tanaka taking New York on a Cinderella run through the playoffs next year, but sadly that opportunity has passed.