Should the Yankees Make a Play for Chris Sale?

The New York Yankees could attempt to speed up their rebuilding process by making a run at Chris Sale of the Chicago White Sox before the trade deadline.

Update: Jon Heyman of Today’s Knuckleball confirms that the Yankees have made overtures to the White Sox about Sale. They’ve been told the price is five top prospects. Heyman says New York remains a long shot to make a deal.

The Aroldis Chapman trade has boosted the already strong New York Yankees farm system into the ranks of MLB’s best. Two of the big pieces in the deal,19-year-old shortstop Gleyber Torres (24th) and 21-year-old outfielder Billy McKinney (75th), are ranked among the Top 100 prospects in the game by MLB Pipeline.

The common assumption among fans is that this is just another step in the Yankees increased reliance on building from within. The team has shown great restraint in holding onto their young talent and avoiding the temptation to add marquee names since their last spending spree in the winter of 2013-2014.

This approach is sensible and should lead to sustained success, but may require more patience than is typically displayed by the New York fan base.

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Joel Sherman of the New York Post recently posited an alternative theory: that the Yankees may be using the Chapman trade to load up on prospects for a run at White Sox ace Chris Sale. The recent friction between Chicago’s front office and their star pitcher makes it at least plausible that the American League’s best starter could be on the move before the trade deadline.

On the other hand, Rob Bradford of WEEI.com cites multiple sources in the game that claim the White Sox are not especially motivated to trade Sale despite the bizarre jersey cutting incident (not to mention his feud with Kenny Williams this spring). Instead, they seem to be exploring what they could get for him this week.

If Chicago does end up trading Chris Sale before the deadline, the price will be understandably sky-high. The Rangers seem to have been the most aggressive club in the early going, and they have reportedly put big names like Joey Gallo and Jurickson Profar on the table, although they have declined to include Nomar Mazara in their package. 

Sale is still just 27 and comes with three years of below-market-value team control. He’s guaranteed just $12 million in 2017, and then has two team options for 2018 and 2019 ($12.5 and $13.5 million). So not only is Sale the league’s best pitcher, but he also has one of the most team-friendly deals in the game.

What would the Yankees have to give up to land three years of Sale? Given the high price the Cubs just paid for two months of a rental reliever, it’s hard to imagine it could be for anything less than four Top 100 prospects plus a nice secondary piece or two.

Aside from Torres and McKinney, the Yankees have Jorge Mateo (26th), Aaron Judge (27th), and Gary Sanchez (50th) in the MLB Pipeline Top 100 list. It would likely take at least four of those five guys to even get the White Sox talking.

Would that be worth it? It just might be. Chris Sale is one of the most valuable players in baseball. It’s hard to see a team fronted by Sale and Masahiro Tanaka not making the playoffs, and if the Yankees actually did go this route, they would presumably supplement the 2017 supporting cast with some follow-up moves.

On the other hand, acquiring Sale would represent the Yankees essentially putting all of their eggs in one very risky basket. No one expected the lanky lefty with the whiplash delivery to stay healthy and durable this long early in his career.

Building your team around a pitcher, even one as good as Chris Sale, is a big gamble. It’s up to the Yankees if they’re willing to make it.