Sale’s Pitch: Envisioning a trade between Yankees/White Sox for Chris Sale

Let’s be honest, the free agent market for pitchers is at its weakest in recent memory. I mean, which pitcher do you consider to be this class’s top starter? Is it 37-year-old Rich Hill? Yawn. Is it Yankee reject Ivan Nova? Don’t get me started. Is it the bearded disappointment Andrew Cashner? Nope. Point being, if any team, including the New York Yankees, wants to make a splash on the market and acquire a top-line starter, it is going to have to happen through the trade market. One name sure to be heavily involved in trade talks is White Sox lefty Chris Sale.

Photo Credit: Joe Nicholson | USA TODAY Sports
Sale pitched his way to his fifth consecutive year as a starter with a sub-3.50 ERA at the top of Chicago’s rotation. With a 17-10 record on a 78-84 White Sox team, to go along with a 3.34 ERA, 1.04 WHIP, 233 strikeouts, and a league leading six complete games, Sale once again displayed his dominance. At age 27, Sale also made his fifth consecutive All-Star appearance in July, being named the game’s starting pitcher. Sale made 32 starts in 2016, pitching another healthy season missing just one start because, well, most of us know the story. But all things aside, Sale is going to be sought out by a number of teams this offseason.

Chris Sale is one of the biggest bargains in baseball. After inking a five year, 32 million dollar deal before the 2013 season, Sale is under contract through the 2019 season, which includes two team options for $12.5 million in 2018, and $13.5 million in 2019. So basically, Sale gets $57.5 after seven years, assuming the club he is with picks up his deal both time. Sale could also make $16 million in 2019, raising the total to $60 million if he wins a Cy Young award in that time, which is entirely possible.

The Yankees will field a rotation with Masahiro Tanaka, Michael Pineda, and CC Sabathia as virtual locks. After that, things get murky as it will likely depend on who performs throughout spring training. Vying for the final two spots in the rotation will be Luis Cessa, Chad Green, Luis Severino, Bryan Mitchell, and possibly Adam Warren. Adding a Chris Sale to the top of the rotation would help solidify and alleviate some of the questions going into the 2017 season.

What teams are truly capable of pulling the trigger on a Chris Sale trade? Large-market clubs are going to be in the running for Sale's services, as the Red Sox, Cubs, Dodgers, and of course, Yankees. Other teams could sneak into the mix, but if Sale is going anywhere, my money says it's one of these four clubs that makes the move to get him. 

Now, there was a point in time where the White Sox were seeking five top prospects for Sale alone. Seeing that nearly no team can meet that price, the asking price from Chicago has likely decreased slightly since then, but getting Sale is going to cause a hit to whatever farm system the White Sox dive into when dealing Sale. Currently, the Yankees have a consensus top-five farm system, so they have the pieces in place to make the move.

What exactly would a Chris Sale trade look like? For starters, the Yankees would definitely have to part ways with either of Jorge Mateo, or Gleyber Torres. Brian Cashman already said he'd be "hard-pressed" to move his top talent, so I'd predict he'd do everything he could to hold onto Torres. To add a proven MLB player, the Yankees could throw in a guy that has popped up in trade rumors for years in Brett Gardner. Adding Gardner to the deal would give the ChiSox a proven and valuable gold-glove outfielder to add to their mix of Adam Eaton and Melky Cabrera, along with lesser-known players they currently roster. The White Sox would also likely want a nearly MLB-ready or MLB-ready prospect, and with Gary Sanchez being untouchable, the Yankees should be more inclined to throw in Aaron Judge or Clint Frazier. However, if the Yankees were to trade Gardner, that would likely point to giving Judge an everyday outfield spot, so Frazier would almost surely be thrown into the deal, as he has an ETA of mid-2017. 

The White Sox would also probably want a young starter, so the Yankees would need to decide who they would throw into this trade between Luis Severino, Luis Cessa, Chad Green, or Bryan Mitchell. With the Yankees intent to fix Severino, and Mitchell already being 25-years-old, I would not expect either of them to be thrown into this deal, but it is a possiblity. In this case, however, it would come down to who the White Sox valued higher, between Green and Cessa. To get a fifth player in the deal, the White Sox may desire a more highly touted starter who is further away from the big leagues. For that, they would look at James Kaprielian, Justus Sheffield, Dillon Tate, or Ian Clarkin. It's impossible to say for certain which pitcher would be thrown into the trade.
Photo Credit: Reed Saxon | AP
So, Cashman could call White Sox GM Rick Hahn with a proposition looking something along the lines of this:
  • Yankees get: LHP Chris Sale
  • White Sox get: INF Jorge Mateo, OF Brett Gardner, OF Clint Frazier or Aaron Judge (probably Frazier), Luis Cessa or Chad Green, LHP Ian Clarkin
Keep in mind, the trade could also look like this.
  • Yankees get: LHP Chris Sale
  • White Sox get: INF Jorge Mateo, OF Brett Gardner, OF Clint Frazier, Luis Cessa/Chad Green, LHP Justus Sheffield
Another note: this is not necessarily a proposed deal, but rather, players that could get the White Sox and Yankees thinking about how they could make this trade work.
Photo Credit: Justin K. Aller | Getty Images
No matter what, Sale will come at a steep price, but I doubt Brian Cashman would be as hesitant if he could pull of a deal similar to these ones, allowing him to obtain one of the best pitchers in baseball, while also retaining most of the players in his already stacked farm system. In the scenario above, the Yankees would retain Gleyber Torres, Gary Sanchez, Judge or Frazier, and James Kaprielian, among many others in their deep farm system. Let's not forget about Greg Bird and Tyler Austin, which the Yankees would also be retaining in this deal.

It is yet to be seen what type of haul the White Sox will receive for Chris Sale if they were to trade him, and we probably won't know until the Winter Meetings in December, where general mangers can meet face to face. Until then, we can speculate and formulate opinions on whether the Yankees should pursue Sale. My mindset has always been this: proven MLB talent is greater than unproven MiLB prospects, and if you can get one of the top players in the game, nine times out of ten, you do it.

Article by: Chad Raines
Follow me on twitter @Chad_Rain
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