Why the Yankees should not be afraid to deal prospects this offseason

The Yankees have reached the offseason doldrums. After signing Matt Holliday and Aroldis Chapman at the Winter Meetings, the team reached its winter spending limit. Hal Steinbrenner set a strict budget and now the club is up against it. This holding pattern has forced Brian Cashman to explore trading veteran players in order to create financial flexibility. Should the Yankees look to upgrade the roster in free agency, they will need to shed payroll first. There’s also the issue of the historically weak free agent class. There aren’t many viable paths for the Yankees to take.

Of course, free agency isn’t the only way to add talent. There’s also the trading block, which offers more creative and cost effective alternatives. The Yankees, however, seem unlikely to part with prospects in order to facilitate deals, and that’s problematic. After the Red Sox acquired Chris Sale, Cashman noted that "...the Sale price tag, you were going to have to ring a bell. We're not prepared to back the truck up and get the one player left that you might need.”

This isn’t the first time that Cashman expressed trepidation over parting with top prospects for a player of Sale’s capacity. “I think that type of deal is a deal where you’re that final piece away,” he said at the end-of-season press conference. “You have to be one piece away, and I would not recommend that type of decision as we approach the 2017 season.”

On the surface level, this reasoning makes sense. The Yankees aren’t the runaway favorites in 2017. They only just recently constructed one of baseball’s premier farm system. There’s no rush to blow it up on the trade market. This offseason, however, doesn’t exist in a vacuum. Trading for impact talent puts the club in a better position for this year and the seasons to follow. A closer look reveals that there are several legitimate cases to be made in favor of trade market activity.

First and foremost, the Yankees have clear areas to upgrade. Starting pitching stands out in particular. The free agent options of Jason Hammel and Ivan Nova are uninspiring. The trading block, however, offers some appealing options. The White Sox are open for business, and Jose Quintana would be quite the addition to the staff. He would not only help this season, but also alleviate some of the uncertainty facing the rotation after 2017. Quintana is the obvious example, but other targets like him are out there. They will be expensive, but the Yankees have the resources to get the deals completed.

That relates directly to the next point: the Yankees can’t keep all of these prospects. Having a premier farm system is nice, it really is. It allows the organization and fans alike to envision a not too distant future where a core of homegrown players take the field. That’s not the only advantage of having a deep system. It also allows for trades. Some prospects are more valuable as trade chips. That’s the nature of the game. Of course there’s risk. Nobody wants to be on the wrong end of a lopsided trade. These risks are worth taking, however, when the club has such depth. There’s a built-in cushion.

Lastly, the narrative that the Yankees should stay put, let the kids play, and wait out future free agents is inherently faulty. There’s no reason to expect that the 2018-2019 free agent class will remain as rosy as it seems now. Players will get hurt, decline, or sign extensions. Trading for established big leaguers now would mitigate some of that risk.

Maybe everything does go right. The Yankees cut spending and reset their luxury rates by the 2018-2019 offseason. Some prospects graduate while others take step backwards. Such is the law of attrition. They’ve been on the periphery of baseball relevance, with no real rotation and an expensive closer. Would that be a club that appeals to free agents? With contract offers and all other financial aspects equal, wouldn’t a player choose the more competitive team? If the Yankees swing trades, however, and demonstrate a competitive streak, then free agents could be more intrigued by New York.

Right now the trade market appears to be the Yankees only path to upgrading the roster. The front office should seriously explore trades and not worry about prospect hoarding. Adding impact talent this winter can better set up future seasons. Trading away prospects doesn’t mean punting on the youth movement. They can do both. Young, cost-controlled players are available on the trade market. The Yankees should be all ears in offers.