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Setting Expectations for the Winter Meetings

Gerrit Cole, fist-pumping in the wrong uniform, courtesy of AP.
Gerrit Cole, fist-pumping in the wrong uniform, courtesy of AP.

Gerrit Cole, fist-pumping in the wrong uniform, courtesy of AP.

Baseball’s Winter Meetings have traditionally been the most frantic week of the MLB off-season. Major Free Agent signings occur, trades are discussed and executed, the Rule 5 Draft occurs, and sometimes even major rule change proposals are announced. The last couple of off-seasons have been atypical due to their relative lack of activity, but there are signs that the Winter Meetings will be action-packed in 2019. As Yankee fans, to what do we have to look forward?

Gerrit Cole, a Yankee?

This one has obviously been telegraphed a bit, but the Yankees have made acquiring Gerrit Cole their number one priority. The Yankees initially drafted Cole out of high school, but he famously turned down the Yankees in favor of pitching for UCLA. The Yankees later tried to acquire Cole via trade during the 2017-2018 off-season from the Pirates, but the Pirates chose the package offered by the Astros over the one offered by the Yankees. In short, the Yankees have always been infatuated with Gerrit Cole, and they have made early movements this off-season to make their intentions known.

Just last week, the Yankees sent a contingent to California that included Aaron Boone, Brian Cashman, Matt Blake, and Andy Pettitte in an attempt to woo Cole even before they provided Cole with a formal contract offer. Today, multiple outlets have reported that the Yankees’ initial offer to Cole is a record-setting 7-year, $245 million deal. Given that this is the Yankees initial offer, and given the likelihood of a bidding war for Cole’s services, Cole’s final contract could be even more eye-popping than those numbers.

Of the teams we know are in the hunt for Cole’s services, the Angels and the Padres will likely be the teams willing to get into a bidding war with the Yankees. Cole may be a California kid, born and raised, but money and team competitiveness are likely greater factors for Cole, particularly given the fact that he is a Scott Boras client.

If I had to make a prediction, I think that Cole will be a Yankee by Christmas, even if the deal doesn’t get done this week. While the Yankees are willing to make Cole the highest paid pitcher in the sport, and sail by the luxury tax threshold in the process, the question remains: if the Yankees sign Cole, how much more is the Steinbrenner family willing to spend this off-season?

Will the Yankee Free Agents Re-Sign?

Brett Gardner, Dellin Betances, and Didi Gregorius are all Free Agents this off-season, but all three have very different outlooks.

Brett Gardner has made his intentions very clear: he wants to return to the Yankees, and the Yankees have said publicly that they are hoping for a reunion as well. My sense is that both sides are just waiting for the Yankees to fill other priorities first before hammering out final numbers on a contract. I can almost hear the wood cracking in the Yankees’ dugout from here.

Dellin Betances is the poster-child for the unfairness of the current system of team control for young players. Betances was one of the best relievers in baseball for his first 5 seasons in the Majors. He spent nearly all of this past season on the IL with a shoulder issue, and his season was ended after his first appearance with a torn Achilles tendon. Betances pitched for years well below market value, and now he can probably be signed for an incentive-laden “prove-it” contract. I have no doubt but that the Yankees will keep in touch with the hometown standout’s representatives, but Betances will likely be in high demand.

Betances has been one of my favorite Yankees, but I fear that there will be a team that strikes first while the Yankees are focusing their efforts elsewhere.

Didi Gregorius is a fascinating case. He proved that he was healthy again in 2019 following off-season TJS, and while his defense was above-average, as usual, he took a large step back at the plate, particularly in the contact and plate discipline departments. Even in his diminished state, Didi was still an average or better everyday SS, but teams will need to consider whether 2019 was a blip, or the beginning of Didi’s decline phase. Didi has been even more than the Yankees could have hoped for since they acquired him from the D’backs, but they have made it clear that they would be willing to play Gleyber Torres everyday at SS, even if it weakens their infield defense. The Yankees also have a crowded infield situation, so Didi may be a luxury as opposed to a need.

Personally, I’d like to see Didi return on a 3-year deal. While many have written-off the Yankees as a suitor, there are not many competitive teams out there in need of a SS, so the Yankees may be able to work out a reunion with Didi for relatively team-friendly terms.


A trade for Francisco Lindor has been the apple of many fans’ eyes since word leaked that the Indians have made the All-Star SS available, but I would be shocked if Lindor were traded this week.

Instead, I think the Yankees will look to fill-out the rotation via trade, even if they acquire a top starter like Gerrit Cole. There has been smoke around the Yankees’ interest in Robbie Ray since last season, though the Yanks and D’backs weren’t able to come together on a deal at the trade deadline in 2019. Both sides have more incentive to get a deal done now, and the Yankees may be tempted to see what new pitching coach, Matt Blake, can do with a strikeout artist of Ray’s caliber.

Even if the Yankees don’t work out a trade for Ray, I fully expect the Yankees to find a deal for a pitcher to fill-out the back-end of the rotation.

As far as Yankees who find themselves on the trading block this week, I don’t think fans will be surprised to see any of these names:

JA Happ

Clint Frazier

Thairo Estrada/Tyler Wade

Deivi Garcia/Miguel Yajure/Chance Adams/Nick Nelson/Albert Abreu, etc.

JA Happ is a contract that the Yankees will certainly try to move this off-season, even if it means attaching a prospect to him to make a deal more palatable. Frazier is a former prospect who certainly has some value at the Major League level, but is a square peg in a round hole with the Yankees. Everyone else are guys who could easily be packaged as part of trades for talent that can help the Yankees win the World Series in 2020. Additionally, the Yankees have a 40-man roster crunch, so the Yankees will surely be willing to part with guys who cannot help the team as currently configured in the next year or so.


This is shaping up to be the most exciting off-season in recent memory for the Yankees. The Winter Meetings will lay the groundwork for much of what happens in 2020. My back-of-the-napkin predictions for this week are:

Gardy re-signs with the Yankees for 1 year/$11 million.

The Yankees trade for a starting pitcher; Clint Frazier, a AAA starter close to the Majors, and a low-level starter are traded in the deal.

Dellin Betances signs elsewhere…and I’m not happy about it.

We learn nothing definitive about where Gerrit Cole will ultimately sign.

Whether my gut calls above are right or wrong, the Winter Meetings will once again be exciting and worth following after two years of dormancy.

#DidiGregorius #ClintFrazier #AlbertAbreu #JAHapp #BrettGardner #DellinBetances #GerritCole

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Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


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