The annual GM Meetings take place from Nov. 11-14 in Scottsdale, Ariz. On hand will be Yankees GM Brian Cashman and his staff, along with representatives from the 29 other teams.
While the big event of the offseason is the Winter Meetings each December, things often start to take shape at the GM meetings.
Here are five questions Cashman should be asked as the GM Meetings begin...
What's the interest level in Gerrit Cole and the rest of the free agent starting pitching top tier?
Cole is the top starting pitcher on the free agent market and could receive the most lucrative contract ever for a starting pitcher. The Yankees are interested, according to SNY's Andy Martino, but landing Cole might be a longshot.
Cashman got defensive during his season-ending press conference when explaining why the Yankees failed to land Cole and Justin Verlander when they were available via trade, and Patrick Corbin when he was a free agent.
When it comes to the 29-year-old Cole, adding him would give the Yankees a true ace as they look to break through and reach the World Series for the first time since 2009. If Cole is too expensive or wants a team on the west coast, the Yanks could instead turn toward Stephen Strasburg or Zack Wheeler.
Is the team willing to eclipse the luxury tax?
This year's luxury tax is $208 million,and the Yankees have worked in recent seasons to get and stay under the cap.
Factoring in raises for expected arbitration raises, the Yanks already have roughly $188.4 million committed to payroll for the 2020 season. That gives them some wiggle room when it comes to staying under the threshold, but things could get dicey if they add a pitcher like Cole.
What about Didi Gregorius?
New York decided against extending a qualifying offer to Gregorius, and will lose him for nothing if he walks via free agency.
Gregorius struggled with the bat this past season after his return from Tommy John surgery, but the Bombers view him as a potential bounceback candidate, according to Martino.
While Gregorius may bounce back in 2020, does he fit in the Yankees' plans?
The Yanks already have infielders Gleyber Torres, DJ LeMahieu, Gio Urshela, and Miguel Andujar under contract for next season.
What is the plan for Miguel Andujar
Andujar had season-ending shoulder surgery in May to repair a torn labrum, and his role for 2020 is very much up in the air.
With the crowded infield and with Andujar potentially being a better fit as a DH, do the Yanks view him as a long-term piece? Or will he provide more value as a trade chip?
The 24-year-old Andujar is under team control through the 2023 season, so the Yanks have no need to rush their decision.