The Yankees have spoken internally about offering contract extensions to arbitration-eligible players like Dellin Betances, Didi Gregorius and Aaron Hicks, according to general manager Brian Cashman, who believes that it could be "now or never" to keep those players in pinstripes.
With that in mind, it would be more likely to see an announcement of that sort from the Yankees in advance of Friday's 8 p.m. ET deadline to non-tender players. Though Gregorius is not expected to return to the lineup until at least June and potentially August after undergoing Tommy John surgery on his right elbow, Cashman said that non-tendering the shortstop has not been discussed.
"Didi is a very valuable player," Cashman said. "I'll have our conversations with [Gregorius' agent] Jim Murray and his agency and see where it takes us. Our plan would be to keep him, and hopefully keep him for a long time."
Sonny Gray is on the list of the Yankees' arbitration-eligible players, and though the right-hander's time in New York appears to be up, the team is likely to offer him a contract in advance of an expected trade. As the Yanks continue to search for starting pitching, seeking at least one more starter, Cashman has been blunt about his desire to trade Gray before Opening Day.

"I just don't think this is the right spot for him. It's nothing against Sonny Gray," Cashman said. "It's been a year and a half. I'm not going to be Sisyphus pushing the rock up a hill and having it roll back on top of me. It's not working."
The Athletics, Braves, Padres, Rangers and Twins have been connected to Gray in published reports. Gray would be a rental for those clubs, as he is set to be eligible for free agency after 2019.
"He will be good again. Trust me," Cashman said. "I believe that honestly. I think he's a heck of a pitcher. The peripherals prove that. He was a very likable teammate. He's a very successful Major Leaguer, and it's just going to happen somewhere else."
The Yanks' other arb-eligibles are left-hander James Paxton, right-hander Luis Severino, catcher Austin Romine, right-hander Tommy Kahnle and first baseman Greg Bird.
Cashman recently confirmed that Romine will be tendered, as there is uncertainty regarding Gary Sanchez's availability for Opening Day coming off left shoulder surgery. In the event that Sanchez is not ready for the season opener, Cashman said that the Yankees would be comfortable going into the year with Romine and Kyle Higashioka as their catching tandem.