Yankees Biggest Moves (and Misses) at the Winter Meetings

Jul 30, 2016; Miami, FL, USA; St. Louis Cardinals left fielder Matt Holliday (7) connects for a base hit during the eighth inning against the Miami Marlins at Marlins Park. Marlins won 11-0. Mandatory Credit: Steve Mitchell-USA TODAY Sports

With the 2016 Winter Meetings wrapping up on Thursday, its time to take a look at what New York Yankees general manager Brian Cashman accomplished during the five-day conference and what work he still has to do.

The New York Yankees entered the annual Winter Meetings with three clear areas of their roster they needed to upgrade: closer, designated hitter, and the starting rotation. Five days later, the front office has taken care of two of those three needs, but one remains a glaring issue both in the short and long-term outlook for the club.

While I’ll get into more depth on the specifics of the team’s transactions shortly, on the whole, the Yankees moves during the Meetings were mostly notable for how boring and predictable they were. Not that they were bad necessarily, just that they could be seen coming a mile away.

One of the fun things about having Cashman as GM has always been that his moves tend to come completely out of nowhere. Trades for guys like Aroldis Chapman, Nathan Eovaldi, Didi Gregorius, Michael Pineda, and Curtis Granderson stand out in my mind as the type of surprising, outside-the-box moves that are signature Cash.

Both of Cashman’s big moves at the Meetings had been predicted by many analysts for weeks before they happened. Maybe that’s a reflection of the fact that they were such good fits for the team that they needed to happen, but it was disappointing as both a fan and a blogger that Cash didn’t get a little more creative.

That said, there was definitely plenty for Yankees fans to get excited about over the last week.

Jul 23, 2016; Bronx, NY, USA; New York Yankees relief pitcher Aroldis Chapman (54) delivers a pitch against the San Francisco Giants in the ninth inning at Yankee Stadium. Mandatory Credit: Noah K. Murray-USA TODAY Sports

Signing Aroldis Chapman

New York’s biggest move of the Meetings was obviously the five-year $86 million contract they gave to the guy generally seen as the top free agent pitcher available this offseason, Aroldis Chapman.

The Yankees have not bothered to hide the fact that the Cuban Missile was their top target since the regular season ended, and ultimately the fit made too much sense for the two sides not to reach an agreement.

Unlike the other big name free agent closers available this offseason, Chapman has already proven he can handle the transition to the more offense-friendly American League, not to mention the bright lights and media scrutiny that come with playing in the Big Apple.

By all accounts, Chapman loved his time in the Bronx and had zero issues on or off the field despite his history. I definitely have some qualms about cheering for a guy with any hint of domestic violence issues surrounding him, but what’s done is done at this point. If he can turn over a new leaf and put this behind him, I guess I will have to as well. I can’t see ever being a huge fan of him though.

The opt-out after year three of the contract actually makes me like the deal considerably more, because it means the Yankees are likely to get Chapman’s age 29-31 seasons before allowing another team to sign him for his decline years.

Apr 28, 2016; Phoenix, AZ, USA; St. Louis Cardinals left fielder Matt Holliday (7) bats against the Arizona Diamondbacks at Chase Field. The Diamondbacks won 3-0. Mandatory Credit: Joe Camporeale-USA TODAY Sports

Signing Matt Holliday

The team also filled their vacant DH spot via free agency, signing Matt Holliday to a one-year $13 million right off the bat on the first day of the Winter Meetings.

Rather than commit four or five years to one of the top available bats like Edwin Encarnacion, Mark Trumbo, or Yoenis Cespedes, Cashman attempted to buy low on one of the National League’s biggest stars from the last decade on a one-year deal.

Even if he doesn’t bounce all the way back to the form that made him a seven-time All-Star with the Cardinals and Rockies, Holliday should be a capable clean-up hitter for a team badly in need of a proven power hitter next year.

Last season was the worst of his 13-year career, and he still put up a respectable .246/.322/.461 (107 OPS+) with 20 home runs and 62 RBI in 426 plate appearances.

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I’d expect considerably better from a professional hitter like Holliday now that he doesn’t have to worry about playing the field, but I could live with a repeat performance of that production in 2017. It would certainly be a big step up from what Alex Rodriguez gave them at DH last year.

Dec 5, 2016; National Harbor, MD, USA; Los Angeles Dodgers pitcher Rich Hill (left) shakes hands with Dodgers manager Dave Rogers (right) at a press conference announcing Hill

Losing Rich Hill to the Los Angeles Dodgers

The New York Yankees were rumored to be one of four clubs in “full pursuit” of the best starting pitcher in the 2016-2017 free agent class, 36-year-old Rich Hill before he re-signed with the Dodgers on Monday for three years and $48 million.

While New York clearly could use an upgrade to their uncertain 2017 rotation, according to Jon Heyman of Today’s Knuckleball, the front office never made a formal offer to Hill. In retrospect, that may because the team was saving its limited payroll space for Aroldis Chapman, who was a safer bet to live up to his contract than Hill, even if the same level of upside wasn’t necessarily there.

After the Chapman and Holliday signings, Cashman told Andrew Marchand of ESPN that he was “tapped out of money for this winter.” It seems like the Yankees were only able to afford two of their top three free agent targets this winter, and ultimately probably took the safer route by putting that money into Chapman and Holliday.

Still, no available free agent had the ability to transform the potential of the 2017 Yankees like Hill, who presented the unique opportunity to acquire a front-of-the-rotation option for just money, on a short term deal. I had visions of Hill and Masahiro Tanaka taking New York on a Cinderella run through the playoffs next year, but sadly that opportunity has passed.

Jul 16, 2016; Oakland, CA, USA; Oakland Athletics starting pitcher Sonny Gray (54) delivers a pitch during the first inning against the Toronto Blue Jays at the Coliseum. Mandatory Credit: Neville E. Guard-USA TODAY Sports

Still No Trade for Rotation Help

General manager Brian Cashman has established himself as one of the best wheelers and dealers in the business during his two decades at the helm. He has a number of impressive blockbusters on his resume, but surprisingly failed to pull the trigger on anything at the Winter Meetings while his club’s chief rival made one of the boldest trades of the last decade.

One of my predictions for the Winter Meetings (at least I got the Holliday signing right) was that the Yankees would finally swing a deal for the young, controllable starting pitcher they’ve been looking for since last winter. Sonny Gray seemed like the obvious choice, but there seems to have been little of substance taking place regarding the Athletics’ ace recently.

The Royals, White Sox, and Diamondbacks were among the clubs rumored to be shopping starters during the Winter Meetings, but while Cashman has said he is leaving no stone unturned in his quest to upgrade the rotation, he seems hesitant to surrender the young talent necessary to land one. When asked by George A. King of the New York Post at the Meetings about the chances of adding a starter, Cash answered:

I don’t anticipate it. It’s a tough market and the price tags are extremely high. We could play on a lot of things because we have a lot of prospects people desire and we desire them, too. I would say it’s less likely for us to acquire a starter.

The decision to trust the loaded farm system and allow it develop slowly rather than cash in prospects to speed up the rebuild is a defensible one, even if it means the Hot Stove League is a little less exciting than it might have been. It’s hard to complain about how the Yankees are positioned for the future right now.

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