To sell or not to sell? That is the question.

The words sellers and Yankees don't seem to fit in the same sentence.

That’s because in the last 27 years, the Bronx Bombers have been perennial contenders for the most part, which typically led to them playing the role of buyers at the annual Trade Deadline.

But in 2016, the Yankees weren’t going anywhere, and they knew it by the time the calendar flipped forward to July. They also had two very attractive trade chips in setup man Andrew Miller and closer Aroldis Chapman.

So, what did general manager Brian Cashman do with these two relievers? He parlayed them into Gleyber Torres, Billy McKinney and Rashad Crawford for Chapman as well as and Clint Frazier, Justus Sheffield and Ben Heller in exchange for Miller.

This made the Yankees’ GM look like a genius, setting up his team for the future by landing an array of top prospects.

As anyone around the game of baseball knows, this game can also be a crap shoot. Besides Torres and Frazier, all of these players are either out of the Yankees’ organization, or out of baseball entirely. The only ones still with the big-league club are Torres and Frazier, who have shown flashes of brilliance at times.

However, the clock has seemingly struck midnight on the Baby Bombers. Both Torres and Frazier have struggled mightily this season, as have the Yankees as a whole, a team in fourth place and eight games back in the AL East with a 46-43 record.

The Yankees are teetering between being buyers and sellers at the deadline and have a need for replenishment, as the constructed roster has a number of flaws.

While New York could theoretically acquire a big-name bat and/or a starting pitcher, they really don’t have too many pieces that could land them a significant return.

Yes, maybe they could trade for a Joey Gallo, or seek rotation help, but will it even propel them into the playoffs in a highly competitive American League? That remains to be seen.


Although it is certainly difficult to envision the Yankees as sellers given their recent history, they need to set themselves up for the future, as well.

They aren’t going to trade their franchise star outfielder Aaron Judge, and it probably wouldn’t be wise to deal Torres, who is under cheap control through 2024. That’s what makes things so tricky, as these two players would bring back the most value.

Getting rid of Aroldis Chapman and Giancarlo Stanton’s contracts would be the key to shedding payroll in order to set themselves up to spend big next offseason without going over the luxury tax. But there aren’t many teams that would be willing to take on their deals.

But there are some other attractive trade chips that reside in the bullpen should the Yankees choose to sell.

Setup man Chad Green, who has posted a 2.89 ERA and 0.79 WHIP, is one name that comes to mind that would make sense to trade. Green is making $2.15 million this year and has one more year of control. Despite dealing with multiple injuries this season, Zack Britton is an additional trade candidate that would help a contender’s bullpen, as is hard-throwing Jonathan Loaisiga, who has gone 7-3 with a 2.11 ERA in 47 innings in relief. Loaisiga is also under cheap control through 2024, though.

Unlike in 2016, the Yankees just don’t have the same rental type, high-valued players to refuel their depleted system.

They do, however, have three talented bullpen arms in the latter trio just mentioned, who could net them some pieces in a season where they appear to be going nowhere.

Unfortunately, due to their identity as an organization, they will likely go against the consensus by tooling up at the deadline to try to make a postseason push, which could jeopardize their long-term blueprint.

If this wasn’t the Yankees we were talking about, the wise decision would be to sell. But in all likelihood, that won’t happen.


Follow Pat Ragazzo on Twitter (@ragazzoreport). Be sure to bookmark Inside The Pinstripes and check back daily for news, analysis and more.