After a 2018 offseason that saw them largely sit out the open market auctions for Manny Machado and Bryce Harper, it appears as if the Yankees will take a more active role in pursuing a top free agent in the 2019 offseason. According to Andy Martino of SNY.tv, the “early feel” from conversations with sources is that the New York organization will at least “engage” with Astros ace Gerrit Cole this winter. At the same time, Martino downplays the likelihood of a successful pursuit.
The Yankees-Cole connection is a longstanding one, so it’s no surprise to see it continue now that Cole is nearing the open market. It was Yankees GM Brian Cashman, after all, that almost landed Cole from the Pirates in 2017–although Pittsburgh ultimately passed on a trade package that was said to center around outfielder Clint Frazier. The Yankees also pursued Cole, a lifelong Yankee fan, back in 2008 when it made him the 28th overall pick in the Rule IV draft (Cole ultimately opted to attend UCLA). After two near-misses, the 2019 offseason should offer Cashman his clearest shot yet at bagging the now-29-year-old Cole.
It’s obvious there’s some level of interest. But it’s equally clear there are significant barriers to Cole donning pinstripes. The New York org could find itself bidding against numerous other teams for Cole’s services, many of which play in or near his native Southern California. And luxury tax implications could prove fateful here. While the Yankees could clear roughly $30MM off 2019’s salary outlay merely by letting CC Sabathia, Dellin Betances, Brett Gardner, and Didi Gregorius head for other pastures, the club would still have some bending to do if it wanted to both sign Cole and avoid a second consecutive year paying CBT overages.
The Yankees already have over $130MM in salary commitments on the books for 2019 before accounting for forthcoming arb raises (including those for Aaron Judge and James Paxton). Since they exceeded the luxury tax line by more than $20MM and paid a 20% overage with a 12% surcharge in 2018, they would incur a 30% tax on every dollar spent over the CBT threshold in 2020 if they again exceed the line, per terms agreed to as part of the 2016 CBA. Still, it’s worth noting that these considerations apparently won’t count the New York powerhouse out of the Cole sweepstakes unequivocally–even if Cashman will have to pull on his creative reserves to make such an acquisition feasible.