Let’s start by acknowledging that there are really no sure-fire starting pitching upgrades available to the New York Yankees this winter. Even the big names come with huge question marks which become even more pressing because of the large salary commitments they will require to sign.
Going into his age-37 season with exactly one season as a starter on his resume (almost a decade ago), Rich Hill might land a three or four-year contract of $50 million or more. Jeremy Hellickson is seen as the “safest” of the top free agent options, and he was below replacement level from 2013-2015 according to Baseball-Reference’s wins above replacement metric with a combined -0.