Yankees have discussed extending Didi Gregorius, Aaron Hicks and Dellin Betances

This offseason the Yankees and GM Brian Cashman are focused on adding talent via free agency or trades, but they’re also considering extending three of their most important players.

Didi Gregorius, Aaron Hicks, and Dellin Betances were three of the biggest contributors on last season’s 100 win club, but this time next year they’ll all be free agents. Unless the Yankees decide to extend them to long-term contracts.

According to Bryan Hoch of MLB.com Cashman and the Yankees front office have internally discussed the possibility of doing just that.

"“Is it something that’s on the list of things to talk to and walk through and get to? Yes,” Cashman said. “I wouldn’t rule anything out. Have we kicked it around in a very small scale way in the offices? Like, it’s now or never? Yeah, we have.”"

Each player is eligible for arbitration this offseason and that should net them a nice raise in salary for the 2019 season. However, if they were to sign an extension their yearly salaries would all see a huge increase over a long-term commitment.

The same is true if they waited to sign long-term deals next offseason as free agents but for the Yankees, it might be in their best interest to lock them up now. If all three made it to free agency next season the organization would have a very hard time bringing each of them back. The truth is it would be highly unlikely.

Aaron Hicks is coming off a career season in 2018 where he established himself as one of the top center fielders in all of baseball. If he can continue to build off his success last season and have an even bigger year in 2019 he’ll be one of the most sought-after players on next years’ free agent market. Hicks at his best is a true five-tool player and he could earn a contract similar to the 5-year $80 million deal the Brewers Lorenzo Cain signed last offseason.

Betances is another player who would be heavily pursued next winter and with the way top relievers have been paid in recent years he could get some huge offers thrown his way. Dellin will be 31 by the time he enters free agency but he’s still square in the prime of his career. Last season he earned $5.1 million after arbitration, but in free agency, he could probably increase that number by as much as $10 million per season.

Because of that Betances is probably the most unlikely to sign any type of extension and wait and see how much he could make as a free agent. Also, the Yankees are more likely to let Dellin test free agency because as we’ve seen in the past they’ve never really offered extensions to their relievers.

What about Didi?

As for Didi if he comes back healthy late next season and finishes the second half strong he should arguably be in line for the biggest payday, between him, Hicks and Betances. Didi has gotten better every season since joining the Yanks back in 2015 and is one of the better all-around players in the league.

I’d consider Didi very underrated, but should he reach the free agent market after having a big August, September and October he’ll be paid like a star and deservedly so. Whether he’s open to signing an extension with the Yanks remains to be seen but if the team wants to lock Didi up they better do so before he has a chance to test the free agent market.

Of course, some could argue that if the Yankees sign Manny Machado this offseason there’s no need to extend Didi, but I’m a fan who believes the Yanks should stay away from Machado. I want Didi to be the Yankees shortstop for another five to six years with Gleyber Torres as his double-play partner at second and Miguel Andujar to his right at third. If Machado signs with the Yanks everyone assumes that either Didi or Miggy will be the odd man out and I don’t want to see either one of them go at all.

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I don’t know how much Didi would be looking for if the Yanks decided to extend him but I think a five year deal for up to $90 million is something they should pursue. Didi could probably get a six-year deal for over $100 million offered his way in free agency but if he truly wants to stay in New York for the long haul I don’t see why he wouldn’t accept that kind of deal.

The tricky part is that Didi is currently injured and nobody honestly knows when he’ll be back next season. That could help the Yankees in negotiations. Since there’s some uncertainty about the timetable of his return the Yanks might be able to get him to sign an extension for a “slight” hometown discount.

As I said if Didi comes back healthy and shows that he’s still an All-Star caliber player in midst of his prime he’ll get paid handsomely next offseason, but there is some risk in him playing the season out. If he struggles coming back from the Tommy John that could end up hurting him in free agency so he might be better off cashing in this winter and signing an extension.

It should be interesting to see how this all plays out, but for the Yankees sake, they should at least attempt to sign all these guys to extensions. if they turn them down well at least they know they tried and they’ll still have as good a shot as anyone to resign them once they hit free agency.