The Yankees have changed the way they operate, there’s no question about that.
Gone are the days when George Steinbrenner would wine and dine the premier free agents himself and open the checkbook at will. His son, Hal, is not operating with deep pockets, and the luxury tax costs have piled up over the years.
Nobody expects the club to spend much this winter, but there’s one big reason why it should, and his name is Jason Heyward.
Let’s start by establishing just how rare it is to find a player like Heyward on the free-agent market.
Heyward has six seasons under his belt with 97 career home runs and 86 steals, but he is still only 26 years old and will be for much of this season. When looking at this winter’s free agents, there are around 20 hitters who are younger than 30 years old, just three are younger than 28 (according to MLBTradeRumors.com), and of those three, none even come close to the pedigree of Heyward.
And it doesn’t get much different in 2017. At the moment, there are just two potential free agents at the end of this coming season that will be younger than 30 — catchers Salvador Perez, who the Royals are already talking potential extension with, and Wilson Ramos.
An established star outfielder who arguably hasn’t even yet reached his prime and had a WAR (Wins Above Replacement, according to Baseball-Reference.com) of 6.2 and 6.5 in 2014 and ’15, respectively, is beyond rare on the free-agent market. He has power, he has speed, and he is probably the best defensive right fielder in baseball. According to Fangraphs.com, he led all RFs in UZR (ultimate zone rating, which attempts to quantify how many runs a player saved or gave up in the field) at +20.2, coming in second among outfielders only to Kevin Kiermaier, who is widely considered the best in the bigs.
The main reason he’s likely coming relatively cheap, if you can consider the expected 7-year, $200-plus million contract coming his way cheap (hint: in today’s league, it is) is because of his career .268 batting average. But he hit a career-best .293 last season with a .359 OBP, and he has cut down on his strikeout percentage for four straight seasons.
Critics will also cite injuries, a big reason why he disappointed after his rookie season, but he played in 154 games last season, so there is no more concern with him as there is for any athlete.
So what’s the drawback? On the surface, there really isn’t one. Heyward is that rare free agent that teams will absolutely regret passing on. But the Yankees, it’s the money, and the roster space.
The team is desperately trying to get under the luxury tax threshold ($189 million in 2016), and with aged star contracts still on the payroll — Mark Teixeira ($22.5 million) and Carlos Beltran ($15 million) through ’16, Alex Rodriguez ($20 million) and CC Sabathia ($25 million) in ’16 and ’17 — money is still tight.

Looking at the current Yankees outfielders, Jacoby Ellsbury and his monstrous contract are entrenched in center field for quite some time, as is left fielder Brett Gardner, who is coming off an All-Star season despite a terrible second half.
Then you have Beltran. The veteran slugger was one of the Yankees’ best hitters down the stretch last year, but it became painfully clear that he really shouldn’t be in the outfield anymore — especially not for 130-plus games. The problem is that A-Rod is already a full-time DH, and Teixeira clearly can’t last a full season playing in the field either. It’s an unfortunate logjam and one that the Yankees have to deal with in 2016. Basically, with A-Rod likely locked in at DH most of the time, there are two spots for Beltran — right field and the bench.
If the Yankees signed Heyward, I think most people would be OK with Beltran being on the bench. He’ll get his time here and there, and with the obvious likelihood of injury with all these old guys running around, there will likely eventually be space for him — and again, this is just a problem for one year. Beltran and Teixeira (woohoo!) are gone after this season, so you’ll have money and roster space available.
Gardner has been involved in trade rumors as the Yankees look to bolster their starting rotation, and moving him could not only clear up some money (he has a base salary of $13 million) depending on who they get in return, but also free up space in the outfield.
There is also the impending breakout of top prospect Aaron Judge. He is also a right fielder and has true power potential. But he has just over 200 at-bats at the Triple-A level, and he hit just .228 there, so there’s still work to do. And if the Yanks add Heyward, a simple adjustment to left field couldn’t be that difficult for Judge, could it?
If the Yankees can just bite the bullet for one year and deal with the luxury tax expenses and potential logjam, then you have your star right fielder of the present and future in Heyward.
What’s the alternative? If you don’t sign Heyward, you put up with awful right-field defense this season and cross your fingers that Judge realizes his potential by 2017. It’s that or you either continue the awful cycle of signing underwhelming aging free agents, or hope and pray Bryce Harper hits the market in 2018, and that you have the $300-400 million to throw at him.