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The case that the Yankees should continue to sell this winter

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Given the condition of the free agent market, should the Yankees get aggressive on the trade market?

MLB: New York Yankees at Atlanta Braves Jason Getz-USA TODAY Sports

It has become something of a cliche to say that the current free agent landscape is awful. After seeing a number of high profile players like David Price and Zack Greinke hit the market last offseason, this year’s crop appears almost laughable. Yoenis Cespedes is the market’s number one target, when just last winter he didn’t even crack the top ten in total guaranteed dollars.

Instead, many have turned the focus to the trade market. With two wild cards, there are perhaps upwards of 20 teams that can convince themselves they’re a mere acquisition or two from contention. Given such a barren free agent market, surely some of those team will be forced to look to trades.

Over at FanGraphs, Dave Cameron argued that a specific team, the White Sox in this case, could take advantage of what should be a seller’s trade market. Chicago certainly would have plenty to offer in, with Chris Sale, Jose Quintana, and David Robertson looking mighty appealing when compared to free agent options.

The Yankees definitely don’t have veteran assets on the level of Sale or Quintana to put forth. However, with the price of mediocre free agents likely to be through the roof, should the Yankees at least consider continuing to sell this winter?

There is certainly an argument the Yankees could stand to gain from a seller’s trade market. Plenty of ink has already been spilled about the Yankees that are most likely to be moved, such as Brett Gardner. Gardner, owed a reasonable $26 million over the next two seasons, would come on much more desirable contract terms than any expensive free agent outfielder.

Just look at Cespedes. In FanGraphs’ contract crowdsourcing project, the crowd estimated Cespedes would earn a $125 million guarantee, despite FanGraphs’ own projections pegging Cespedes as a 3 WAR player in 2017. With a nine figure guarantee required to snag Cespedes, a solid player like Gardner on his deal should seem alluring.

Of course, there’s also Brian McCann. At $34 million over the next two years, McCann’s contract is a bit more onerous, but still eminently movable. The Astros have already reportedly expressed interest, with a left-handed power bat their top priority. Given that comparably valuable free agent catchers, such as Matt Wieters, are likely to earn similar guarantees to what McCann is owed, the Yankees will have to include salary relief if they want a McCann trade to bring a notable return.

Once beyond the Yankees that are consistently mentioned in trade rumors, things get more interesting. In a starting pitching market where Jeremy Hellickson could very well earn over $60 million, should the Yankees look at trading a starter like Michael Pineda? All of baseball is aware of Pineda’s frustrating nature, but also of his still evident talent. As an average-ish pitcher with upside making relative pennies (projected salary of $7.8 million), Pineda would probably be attractive to many teams.

What of the middle infield combination? Yankee fans would be loathe to see Didi Gregorius go, but a trade of Starlin Castro would be more palatable. With Ian Desmond moving to center field, Neil Walker is very literally the only quality middle infielder on the market. Castro is a middling player, but his contract is fairly cheap, and an infield-needy team that misses on Walker would have hardly any other external options.

And if the Yankees did decide to make Gregorius available, interest around the league would be tremendous. In MLB Trade Rumors’ ranking of the top 50 free agents, not a single shortstop earned even an honorable mention. Surely the Yankees have no intention of trading him, but it could be worth sniffing around to see if there’s a shortstop-hungry team willing to offer the moon for a quality young player like Gregorius who offers multiple years of team control.

A sale of any great magnitude is unlikely, since the Yankees still want to compete next year. Yet even if the Yankees did take advantage of this trade market and moved players like Gardner, McCann, and Pineda, it’s very possible that the team could both recoup a decent prospect haul from those players and remain competitive in 2017.

Obviously, the Yankees have Gary Sanchez penciled into the starting catcher slot, so McCann probably has more value to another team. The outfield and starting rotation are more shaky. Still, Aaron Judge and Aaron Hicks are likely to bounce back at least somewhat in 2017, and the Yankees do have a number of intriguing depth options for the back of the rotation.

Plus, should the Yankees trade veterans, they would in all likelihood clear a significant amount of payroll. The Yankees always have plenty to spend in general, and they also just shed the contracts of Carlos Beltran, Aroldis Chapman, and Mark Teixiera. Yes, we did just spend plenty of time talking about how poor the free agent market is, but a Yankee team with tens of millions to spend should be able to at least plug a couple of holes created by trades.

None of this is extremely likely. It’d be a bit surprising to see both McCann and Gardner in a Yankee uniform next season, but other blockbuster deals aren’t probable. Regardless, the idea of continuing to sell should at least be explored by the Yankees’ front office. Any team that commits to trading veterans this winter might be able to take advantage of a seller’s market. In the Yankees’ case, with their excellent farm system and unlimited financial resources, a small sell-off wouldn’t even have to significantly impact the team’s 2017 chances.