Yankees Should Roll the Dice on One of These Risky Starting Pitchers

The New York Yankees should target uncertain but high-upside arms on one-year contracts this offseason to add depth to their thin starting rotation.

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 -0.7 WAR for those three seasons.

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 -0.7 WAR for those three seasons.

Do I really need to tell Yankees fans why signing Ivan Nova to the four-year $52 million contract MLB Trade Rumors projects for him would be risky? Before making 11 good-but-not-great starts for the Pirates down the stretch, Nova hadn’t been even an average MLB starter since 2013. He missed most of 2014 with TJ surgery and had more than a full season’s worth of terrible performance after returning.

I’ve previously said signing Rich Hill would be my top priority this winter if I was GM because, well, it isn’t my money. Any move that only comes with a financial cost has little downside from my perspective. I’m focused on the product on the field, which Hill would certainly help, not profits.

If giving that kind of cash to Hill is too much of a risk for New York’s ownership, however, there are plenty of other high-upside plays the Yankees could make on one-year commitments this winter. Here’s a look at three free agent lottery tickets who could pay off big for the team in 2017.