NEW YORK -- Ten years ago -- the last time that the Winter Meetings were held in Las Vegas -- Yankees general manager Brian Cashman slipped out of his hotel suite and boarded a commercial airliner bound for Northern California, authorized to drop what was then the largest contract ever issued to a free-agent pitcher on Carsten Sabathia's doorstep.
The seven-year, $161 million pact that Cashman and Sabathia agreed to in the hurler's spacious living room served as the first major piece in a spending spree that would see the Yankees add A.J. Burnett and Mark Teixeira. That trio played a major role in helping the club inaugurate the new Yankee Stadium with the 2009 World Series championship the following autumn.
It has been nearly a decade since the Yankees appeared in a World Series, though they were one win away in 2017 and are coming off a 100-win regular-season campaign, third most in baseball behind the Red Sox (108) and Astros (103). With James Paxton having already been added to the rotation this offseason, Cashman believes that the Yanks can use the Winter Meetings as a springboard to reinforce and upgrade their roster for '19.

"We had one of the elite teams in the game last year," Cashman said. "We've been one of the better teams in baseball the last several years. We can't lose focus of that, but at the same time, we've fallen short of our goal, which is to try to become a [World Series] champion. We're going to keep driving through that until we can punch through. I've done it before, and I want to do it again. We all want to do it again."
Club needs
Cashman has said that he must add at least one more top-level starting pitcher to a mix that includes Luis Severino, Paxton, Masahiro Tanaka and Sabathia. The Yankees will also need to address their middle infield, with shortstop Didi Gregorius expected to be rehabbing until at least June. Bullpen help is required, with Zach Britton and Player Page for David Robertson having filed for free agency, and a left-handed bat would add balance to the lineup.
"The defending world champs reside in our division, as well as the previous year's world champs in our league," Cashman said. "I think the American League is the elite league, and so we have to find ways to close the gap."

Whom might they trade?
Sonny Gray will be traded before Opening Day, with the Brewers and Padres having been listed among interested clubs. Teams have asked about Miguel Andujar and Gary Sanchez, among others, though those proposals have been rejected. The Yanks would love to move Jacoby Ellsbury, having recently shopped him to the Mariners, but as of yet, a match hasn't be found.
"There's trade opportunities that exist in the marketplace, as well as free agents," Cashman said. "If we can find the right matches, we're willing to act on it."
Prospects to know
With Justus Sheffield having been traded to Seattle in the Paxton deal, the Yankees' top prospect according to MLB Pipeline is outfielder Estevan Florial, a 21-year-old speedster who showed flashes of excellence this past year at Class A Advanced Tampa despite missing eight weeks due to right hamate bone surgery. Right-handers Albert Abreu, Domingo Acevedo, Chance Adams, Michael King, Jonathan Loaisiga and Freicer Perez could all see big league time in 2019.

Rule 5 Draft
The Yankees' 40-man roster is currently full, having recently added right-hander Joe Nelson to protect him from being selected in the Rule 5 Draft. The Yanks would have to subtract a player from the 40-man in order to make a selection, but New York could lose several players from its Minor League system in Thursday's Draft. Left-hander Nestor Cortes Jr., first baseman Mike Ford, infielder Kyle Holder and right-hander Adonis Rosa are among those who could draw interest.
Payroll summary
After resetting their luxury-tax rate this past year, avoiding their first penalty since the tax was instituted in 2003, Cashman and team president Randy Levine have said that managing general partner Hal Steinbrenner is prepared to exceed the threshold of $206 million in '19.
The Yankees have approximately $102.8 million committed to Giancarlo Stanton, Tanaka, Ellsbury, Albertin Chapman, Sabathia and Brett Gardner. Raises are also due to arbitration-eligible players, a group that includes Gregorius, Gray, Paxton and Dellin Betances. Taking into account others on the 40-man roster and estimated player benefits, they appear to have at least $25 million of available space under the tax threshold.
"Hal Steinbrenner and the Steinbrenner family have always been massively supportive of this franchise for the fans," Cashman said. "We're capable [of exceeding the threshold]. We'll see if we execute on that level, if this is the winter that we choose to do that, or if we go a different direction."