NEW YORK -- Once Brian Cashman's feet are safely on the ground Sunday evening, again set to dangle off a Stamford, Conn., office tower in his annual role as one of Santa's rappelling elves, the general manager plans to hustle to Southern California in hopes of delivering a few pre-Christmas gifts for Yankees fans.

The Winter Meetings are scheduled to take place from Sunday through Thursday at the Manchester Grand Hyatt in San Diego, and with the Yanks prioritizing the pursuit of starting pitching above all else, Cashman and his baseball operations department figure to be busy as they work their contacts and engage with the representatives for the premier free agents.

What is the likelihood of Gerrit Cole wearing pinstripes?

This is the number one question on the mind of any Yankees fan, especially after Cashman, manager Aaron Boone and new pitching coach Matt Blake traveled to Southern California this week to meet with Cole, sessions that were said to go well. The club also met with Stephen Strasburg, but the reigning World Series MVP re-signed with the Nationals for seven years and $245 million on Monday.

The Yanks opened discussions with Cole's representatives at the General Managers Meetings in November, though that was more of an information-gathering exercise. What did they learn?

"There's going to be some opportunities for some people to take advantage of their great performance in this marketplace," Cashman said. "They're going to come out really, really well. They've earned that right and they're going to be happy with whatever contracts they get. It just depends on where they're going to get them, and where they choose to accept them."

Either hurler would provide a terrific addition, not only for 2020 but beyond, as James Paxton and Masahiro Tanaka can both be free agents after '20. The hang-up will be the price, but the Yankees' contingent wouldn't have flown 6,000 miles round trip if they weren't willing to write a big check, and managing general partner Hal Steinbrenner has said that "all options are open" in free agency.

"We're just going to put our best foot forward, making sure we can share who we are, what we represent," Cashman said. "We're not going to make any assumptions that what [they] read in the papers is good enough. We're going make sure that we put our educational component in … try to make sure that they understand what our culture is, the personnel we have here to serve you and the great operation that the Steinbrenners allow to be run here."

If not Cole, then who?

Expect to see the Yankees cast a wide net in the pitching department -- as Cashman recently said, "There might be some others that could be impactful, that might not be as pretty or sexy out there in terms of name recognition." That could be true on the trade side as well; last November, for example, the Yanks were able to acquire Paxton from the Mariners for three prospects. A similar swap would be a nice boost.

The Yankees have spoken with the representatives for free agent Madison Bumgarner and others. At present, the rotation projects to feature Tanaka, Paxton, Luis Severino, J.A. Happ and perhaps Jordan Montgomery, with Domingo Germán's status still unsettled (MLB has yet to announce discipline, but it's likely German will be unavailable for Opening Day). Steinbrenner has said that he believes in that group, but the Yanks would like to upgrade if possible.

Are the Yankees trying to re-sign any of their free agents?

Yes. The most likely reunion is with Brett Gardner, and coming off a productive season, the longest-tenured Yankee is expected to score a deal that provides a raise over the $9.5 million he earned in 2019. Gardner's return is important because the Yanks do not expect to have Aaron Hicks until at least June due to Tommy John surgery; Gardner can handle duties in center field, where their only other realistic option is Mike Tauchman.

Dellin Betances, Didi Gregorius and Austin Romine are all free agents as well, and not surprisingly, the trio has drawn interest from Joe Girardi's Phillies. The Yankees would like to have those players back, but it's possible they will be outbid on all three, as Cashman feels they are covered in the bullpen, at shortstop (Gleyber Torres) and backup catcher (Kyle Higashioka).

Other than starting pitching, where will they try to upgrade?

Cashman has expressed how difficult it can be to upgrade a team that won 103 games in the regular season, and accordingly, most of their tweaks could be on the margins. Maintaining the strength of a power bullpen would be one avenue, and the Yankees have been connected to Blake Treinen, who was non-tendered by the A's, and the Royals' Tim Hill as targets in recent days.

Which players would the Yankees trade?

The Yankees have been receiving numerous calls regarding third baseman Miguel Andújar, who was supplanted this past season by Gio Urshela. The club is considering having Andújar expand his versatility by adding first base and left field to his portfolio, but a swap could also be possible -- the Rangers are said to be one of the intrigued clubs.

Clint Frazier's future in pinstripes also remains unclear, especially if the Yanks intend to have Giancarlo Stanton starting regularly in left field.

What if they leave San Diego without a major acquisition?

That wouldn't be a shock, especially since Cole is not expected to come off the board in San Diego. In past years, the Yankees have used the information gathered at the Winter Meetings to pull off swaps in the weeks before pitchers and catchers report to Spring Training -- last year at this time, for example, they were still trying to offload right-hander Sonny Gray.

"We'll go to town with our scouts and our analytics and our front-office personnel," Cashman said, "and map out hopefully a successful strategy for the 2020 campaign that leads us to a world championship."