Thing to watch from the Yankees at the winter meetings in San Diego:
Pitching the pitchers. General manager Brian Cashman, who met face-to-face last week in California with Gerrit Cole and Stephen Strasburg, is likely to again engage with Scott Boras, who represents the pair, in San Diego.
Dollars were not discussed in either meeting, but expect some numbers to be exchanged in the coming days. It’s unlikely — though certainly not impossible — that either pitcher will be signed during the meetings, but by week’s end, the Yankees’ chances of signing one of the two (Cole is their top target) should come into focus.
Don’t forget about the Yankees' free agents. Since free agency began last month, Cashman has maintained contact with the representatives of four of his own free agents: Didi Gregorius, Dellin Betances, Brett Gardner and Austin Romine. Of the four, Gardner is the most likely to be back, and there are indications that a deal could be forthcoming soon. He's followed by Betances, who would have been due a huge payday if he had not been hurt pretty much all of 2019. As for Gregorius, the Yankees are comfortable with Gleyber Torres shifting to shortstop and DJ LeMahieu taking over everyday duties at second. Romine, though beloved by pitchers and a clubhouse leader, has never been a favorite of the club’s analytics department, which for years has favored Kyle Higashioka.
Uncertainty in center. Aaron Hicks, signed to a seven-year extension last February, will miss at least the first two months of the season — and likely a bit more — as he recovers from Tommy John surgery on his right elbow. That would seem to add urgency to bringing Gardner back, but the Yankees could pivot last-minute and choose to explore other — and younger — outfield options on the market, whether it be through trade or free agency.
Keep an eye on Miggy. Miguel Andujar went from AL Rookie of the Year in 2018 to mostly forgotten man in 2019 because of a shoulder injury that limited him to 12 games, setting the stage for the rise of Gio Urshela. Cashman has said the third-base job is Urshela’s to lose and hasn’t ruled out a position change for Andujar, who is of major interest to more than a few teams and could be a significant trade chip in a blockbuster deal.
Don't sleep on the trade market. While signing Cole has become No. 1 on the club’s winter wish list, some of the Yankees' biggest offseason splashes of late have come via trade, James Paxton last offseason being the most recent example. The Yankees traded for Giancarlo Stanton in 2017, Starlin Castro in 2015 and Gregorius in 2014.