Predicting the Yankees’ Moves at the Upcoming Winter Meetings

Yanks Go Yard takes an early look at what New York Yankees general manager Brian Cashman could get up to at the upcoming Winter Meetings in National Harbor, Maryland.

The annual MLB Winter Meetings, which run from December 4 to 8 this year at the Gaylord National Resort and Convention Center, just outside of Washington D.C., are almost always the busiest and most exciting event of the Hot Stove Season, and the New York Yankees appear poised to be at the center of the action for this winter’s festivities.

Yankees GM Brian Cashman has reportedly been in consistent contact with a number of the biggest names on the free agent market since the start of the offseason, most notably sluggers Edwin Encarnacion, Jose Bautista, and Yoenis Cespedes, starting pitchers Rich Hill and Jason Hammel, and their rumored top target of the winter, former closer Aroldis Chapman.

Given the amount of buzz the club has generated on the rumor mill thus far, it wouldn’t be surprising if they made at least one big signing from that group during the Meetings. There can’t be that much smoke without at least a little fire, right?

The team’s biggest needs at the moment are an everyday DH, a closer, and a starting pitcher. The first two are readily available on the free agent market, but the lack of quality starting pitching options aside from the injury-prone Hill may lead Cashman to explore a deal for a young starter.

With executives from all 30 MLB clubs in one place for four days of non-stop negotiations, the time seems right for Cashman to finally pull the trigger on a deal for the rotation building block they so desperately need.

Let’s take a stab at predicting some of the moves the Yankees might pull the trigger on during the course of the Meetings. To be clear, I don’t expect all of these deals to get done, but I wouldn’t be surprised if one or two of them became a reality.

Signing Matt Holliday to Fill the DH Vacancy

Buster Olney of ESPN recently reported that the Yankees were on the lookout for bargains to fill their designated hitter job because of the “flush buyers’ market” for veteran sluggers. While I would love to see them go for a premium model like Edwin Encarnacion or Jose Bautista, I just don’t see them going three to four years on a guy like that when they have so many other viable options.

John Heyman of Today’s Knuckleball revealed in a recent column that the team has been in contact with Holliday’s representatives, and it seems possible they could swoop in with a healthy one-year offer next week during the Meetings and take care of that need early. Something in the $10-12 million range should probably be enough to get Holliday to put pen to paper.

Even during a “down” 2016 campaign, Holliday put up a solid .246/.322/.461 (107 OPS+) batting line with 20 home runs and 62 RBI in 426 plate appearances. Most of that value was given back with his poor work in the field, but moving to DH full-time will put an end to that problem.

Holliday will turn 37 in January and has struggled to stay on the field the last two years after a decade as one of the most consistently productive power hitters in the game, so the whispers about his decline are inevitable.

Given his exceptional talent, however, I would be willing to bet he has one or two seasons as an above-average middle-of-the-order bat left in him. The Steamer projection system agrees, predicting a .275/.358/.465 (121 wRC+) with another 20 homers, 70 RBI, and 1.8 WAR.

Trading for Sonny Gray (or a similar controllable starter)

Despite the denials of GM Brian Cashman during his end of season press conference back in October, I could definitely see the Yankees making a big move for a controllable starting pitcher during the Winter Meetings, just maybe not one who would cost the entire farm like Chris Sale.

Sonny Gray is my pick kind of by default. It’s been reported already that Oakland is willing to listen on him and their other veterans because they don’t see themselves as contenders next year.

Presumably, the 27-year-old right-hander would come at a significant discount after putting up a 5.69 ERA and 4.67 FIP in 117 IP (22 GS) in 2016. The obvious explanation for his struggles were the two muscle strains in his pitching arm that required him to miss much of May, August, and September.

Gray had been one of the most exciting and dominant young starting pitchers in baseball the previous three seasons, pitching to a 2.88 ERA and 3.36 through the first 491 innings of his career (74 GS). He made his first All-Star squad and finished third in the AL CYA voting in 2015 before completely falling off a cliff last year.

The problem with acquiring Gray is that because of his youth, three years of team control remaining, and extensive resume, Oakland can price him (almost) as if he is still an ace despite his ugly numbers in 2016.

If that difference proves too difficult to work out, I fully expect to see Cashman net another solid number two or three starter with multiple years of control this offseason, most likely during the frenetic action of the Meetings.

Other names I’ve thrown out since the end of the season in our “Offseason Trade Target” series include Carlos Rodon, Sean Manaea, Jon Gray, Robbie Ray, Archie Bradley, Michael Wacha, Jaime Garcia, Tyson Ross, Matt Shoemaker, and Gio Gonzalez.

Next: Which Former Yankees Will Be Elected to the Hall in 2017?

There have been indications that all of those guys are available to varying degrees, and the majority would provide the Yankees with a significant rotation upgrade in 2017 and beyond.