What Will A Week In San Diego Bring The Yankees?

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Mandatory Credit: ut-sandiego.com

Overview

New York Yankees General Manager Brian Cashman and his staff head to the west coast this week for the annual Winter Meetings. While a couple of items have been checked off the list, Cashman and the Yankees still have some question marks on the table that need to be addressed, hopefully by the end of the week.

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Coming into San Diego, the Yankees have their fourth outfielder, their shortstop, and their setup situation in the bullpen apparently resolved. While Cashman has said that recent trade acquisition Didi Gregorius and reserve infielder Brendan Ryan will platoon until one of the two separates themselves as the starter, I can’t believe that Shane Greene was dealt for a platoon player. Could another option be on the horizon? Most likely not, but the Yankees have items on their holiday wish list that they would like handled before Christmas, and hopefully, have some additional players signed by the end of the week.

It was this time last year, that things changed in the Bronx forever. Brian McCann was already a Yankee, Robinson Cano and Jay-Z took the money and ran to the west coast, and the Bombers were preparing to poach another member of the hated Boston Red Sox. What questions will the 2014 Winter Meetings answer? Let’s take a closer look!

Will Chase Headley Return To The Bronx?

With the enormous deal that Pablo Sandoval signed with the Boston Red Sox just under two weeks ago, it set up free agent third baseman Chase Headley for a huge payday–deserved or not. The former Friar has had interest from Cleveland, Miami, the Giants, and even the Padres(?) The Yankees would like to retain Headley, but at their price and their length of contract.

Originally, it was believed that the Yankees would be able to easily keep their trade acquisition without much effort, but as the market has heated up, so have Headley’s suitors. There are rumors that he has a four-year offer on the table, for more than $60 million dollars. Believe me when I say this, the Yankees will not go that long or that deep with Martin Prado and Alex Rodriguez ready to man the hot corner in the Bronx next season and beyond.

Prediction: Headley signs his 4-year deal, and it’s with the San Francisco Giants

Joy R. Absalon-USA TODAY Sports

Will The Yankees Wait Too Long And Miss Out?

Another great trade acquisition by Cashman prior to the trading deadline, Brandon McCarthy‘s career was resuscitated upon arriving in the Bronx. After leaving the Arizona Diamondbacks, the righty workhorse posted a 7-5 record with an ERA of only 2.89. Both McCarthy and the Yankees have plenty of mutual interest in a deal that will keep him in New York, but we have yet to hear much of anything regarding a negotiation. We do know one of his former teams, the Texas Rangers, have stated they have interest in a reunion as well.

The question is, will the Yankees wake up, and get this deal done before anyone else can come along, snatch up McCarthy, and leave the Yankees with yet another hole to fill in their rotation? They can’t feel confident with the return of C.C. Sabathia in the back of the rotation, and the inability for Michael Pineda to stay healthy. Cashman traded some of the team’s depth to the Detroit Tigers, when Shane Greene was jettisoned for Didi Gregorius as part of a three-team deal last week. The Yankees have two glaring holes in the rotation, and McCarthy should be a priority to be brought back. If the Yankees overlook this issues because of their obsession with David Robertson, this team is in trouble heading into 2015.

Prediction: McCarthy returns to the Yankees on a 3-year deal, for $36 million dollars

Will The Yankees Break The Bank And Give Out Another Mega-Deal?

Rumors have circulated now for the past couple of weeks, that Max Scherzer and the Yankees have been quietly negotiating a deal that would bring the former Cy Young winner to the Bronx. Those rumors have been argued back and forth by various members of the media, with some saying they are legit, while outlets controlled by the Yankees (YES Network) have said the reports are “inaccurate.” So which is it? Scott Boras is Scherzer’s agent, and he likes to stir up the pot, but for me, where there is smoke, there is fire.

The Yankees could certainly use a big time pitcher in their rotation, with Pineda and Sabathia as question marks, and no guarantee that Brandon McCarthy returns to the fold. Add in the fact that Hiroki Kuroda will either retire or head back to Japan to pitch, the Yankees need at least two starting arms for the rotation. But does a 6-year, $200 million contract make sense for a guy with ONE CAREER COMPLETE GAME and whose velocity is starting to drop at an alarming rate? There are cheaper, better-suited options for the Yankees, and unless they want a repeat of the situation they have with C.C. Sabathia, they’ll avoid signing Max Scherzer like the plague. But, this is the Yankees.

Prediction: The Yankees sign Mad Max to a 7-year, $185 million contract

For Once, Will The Yankees Use Some Common Sense?

It’s highly unlikely that free agent lefty Jon Lester will ever don Yankees’ pinstripes, but in reality, it’s the move that should be New York’s priority. Left-handed pitchers are custom built for the Bronx, Lester is more polished as a pitcher than either Scherzer or James Shields, he has plenty of AL East experience, and doesn’t depend on a high-90s fastball to make his living. He is crafty, and smart, and he has the target of the Boston Red Sox on his back.

The name of the game is improving your team while weakening your opponents. The Yankees did just that last season by signing away Jacoby Ellsbury, and they can really strike fear into the rest of baseball if they were to come in over the top on Lester, and give him a deal that blows everyone else away. Boston owner John Henry is so obsessed with bringing Lester back to Boston, that he paid a visit to Lester’s Atlanta home this past weekend.

I see Lester aging gracefully like a Tom Glavine, rather than having his skills deteriorate to the point of uselessness like Sabathia. He would be the perfect #2 behind Masahiro Tanaka, and in front of Michael Pineda. Add in McCarthy and Sabathia on the back end of the rotation, and it would be both deep and experienced. This is the move the Yankees must make. If they allow Lester to return to Boston, and overpay for Scherzer, the Red Sox will help send the Yankees into a tailspin that could last for the next half decade.

Prediction: Lester returns to Boston on a 6-year, $155 million deal

Mandatory Credit: Anthony Gruppuso-USA TODAY Sports

Will The Yankees Overpay For Something They Have Plenty Of?

The front page story over the past several weeks is whether or not the Yankees and closer David Robertson will settle their differences and come to an agreement on a new contract. The heir to the Sandman, Robertson had a solid first year as a closer, but he might be on the greedy side, looking for “Papelbon money”, meaning he wants in excess of $50 million for his new deal. That is a tough pill to swallow for the Yankees for a couple of reasons. #1. He’s only been a closer for one season. #2. Closers simply aren’t worth that kind of money and #3. Dellin Betances.

The Houston Astros and now the Chicago White Sox appear to be leading the pack for D-Rob’s services. The Yankees offered the righty a qualifying offer, but he declined the one-year, $15.3 million deal to hit the open market. Unfortunately for the Yankees, if either team signs Robertson, their draft pick is protected due to being a top 10 selection. The Yankees instead, would get a sandwich pick at the end of the first round.

The Yankees by signing Andrew Miller, trading for Justin Wilson, and having super prospect Jacob Lindgren along with Betances, they could have one of the best bullpens in all of baseball. Why add $50 mil more to the payroll for a guy who is good, but not great? Take the draft pick, save the money, and wish him the best. The Yankees had to face the same issues after the 1996 season when John Wetteland took the money from Texas and left the closer’s role to an unproven Mariano Rivera. Worked out okay didn’t it?

Prediction: Robertson will sign with the Astros for 4-year, and $50 million…and get dealt within 2 seasons to a contender when Houston doesn’t contend and they don’t want to pay that deal.

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