Four Yankees questions ahead of the 2019 Winter Meetings

After a steady build-up over the past few weeks, the 2019 Winter Meetings are here. We’ve already seen a fair amount of hot stove activity, but things are about to get kicked up a notch. This is the busiest stretch of the offseason, as the entire industry will converge in San Diego to hammer out deals, trades, and everything in between.

Let’s get ready for the week to come with a look at the main talking points heading into the winter meetings.

1. Are the Yankees for real this time?

We know how the Yankees’ pursuit of top free agents went a year ago. While the Bombers still had a successful 2018 offseason overall, they did not bring their A-game when it came to the likes of Manny Machado, Patrick Corbin, and Bryce Harper. New York didn’t make competitive offers to any of the top-three players on the board, instead letting big-market behemoths like, *checks notes*, the San Diego Padres out-bid them for some of the game’s brightest stars.

We don’t have to re-litigate whether passing on those players was a smart move, but there’s no question the Yankees pretty actively decided against using their full financial clout last year. The tenor is completely different this time around:

The Yankees appear to insist that when the rubber meets the road, they’ll have the cash on hand to sign a top free agent. They’ve met with both Gerrit Cole and Stephen Strasburg thus far, and sound more committed to making an actual offer to both, with ESPN’s Jeff Passan reporting that signing Cole is the Yankees’ “top priority”.

This rhetoric means little until the Yankees actually put a contract in front of Cole or Strasburg. They can take all the meetings in the world and make all the promises regarding bags of money, but it’s all moot if they don’t show up at the end of the day with a legitimate offer.

There seems to be much more reason to believe they’ll follow through this time. There’s a sense that a top starter is what could push this team over the top, much like CC Sabathia did 11 years ago. Let’s hope Brian Cashman and Co. make it happen.

2. Is there a backup plan?

Earlier this week, the Phillies signed Zack Wheeler to a five-year, $118-million contract. The signing takes a secondary option for the Yankees off the board. Interesting, however, is the fact that the White Sox reportedly had a stronger offer on the table for Wheeler. Reports indicate Wheeler chose Philadelphia due to the city’s proximity to his wife’s hometown.

It wouldn’t be impossible for something similar play out with New York. The Yankees could plausibly make the biggest offers to Cole and Strasburg, only to see both right-handers turn them down for cities they prefer. Cole is from Southern California, and Strasburg has long been rumored to want to stay in Washington.

Do the Yankees have a backup plan if Cole and Strasburg simply decide they’d rather play somewhere else? Will they be able to refocus on a second-tier option, at a time when those options are already getting snatched up?

Not only has Wheeler signed, but Cole Hamels signed with the Braves, Kyle Gibson signed with the Rangers, and Jake Odorizzi re-upped with the Twins. Talented players still remain, such as Madison Bumgarner, Dallas Keuchel, and Hyun-jin Ryu, but the choices are already dwindling.

The Yankees absolutely should play at the top of the market, yet there’s some risk involved. No amount of money can literally force Cole or Strasburg to sign, and if the Yankees fail to secure either, they’ll need to pivot quickly. Hopefully, if neither of the big fish decides to come to the Bronx, there are still some quality pitchers left unsigned.

3. Will Cashman find a taker for J.A. Happ?

At the 2017 Winter Meetings, the Yankees made a low-profile move to send Chase Headley and Bryan Mitchell to the Padres. The trade left San Diego with the bill for the last season on Headley’s contract, and freed up roster space for young players like Miguel Andujar.

Such a maneuver could be in J.A. Happ’s future. Happ was a boon to the Yankees’ rotation in 2018, but the veteran left-hander struggled last season in the first year of the two-year, $34-million pact he signed ahead of 2019. Rumor has it the Yankees are trying to package another player, possibly a prospect, with Happ to convince a team to take on Happ’s salary.

I find little joy discussing the literal New York Yankees attempting to pull off a salary dump, but even I would be somewhat impressed if Cashman duplicated the feat he pulled off with Headley in the case of Happ. While the Yankees don’t need any help salary-wise, moving Happ would have clear benefits in terms of the roster. If the Yankees do land a big starting pitcher, they’ll need another slot in the rotation. Sending off Happ would also clear the way for younger, more exciting options, like Deivi Garcia, Jordan Montgomery, Michael King, and any number of other interesting prospects on the farm.

We’ll see if the Yankees do find a taker Happ, or if they keep the left-hander around as pitching depth.

4. What about the Yankees’ internal free agents?

The Yankees have a decent bit of talent hitting the market this year, namely Didi Gregorius, Dellin Betances, and Brett Gardner. There’s already been plenty of buzz surrounding Gregorius and Betances, with that pair drawing notable interest from the Phillies, who have Joe Girardi on as manager and have signaled a desire to make big moves this winter.

Will the Yankees make a play to retain one or all of those three, or will they stay singularly focused on the top of the market? New York could sustain the loss of Gregorius by shifting Gleyber Torres permanently to shortstop, but that would leave the infield looking somewhat thin. The bullpen is deep as always, but a short-term reunion could make loads of sense for both Betances and the Yankees.

A return from Gardner has also generally seemed likely, what with the veteran’s status as the longest-tenured Yankee and his strong performance in 2019. Jon Heyman reported yesterday that the Yankees had made an offer to Gardner. Keep an eye on this trio to see if the Yankees can settle their roster a bit this week simply by keeping things in-house.