Yankees: Buster Olney says Didi Gregorius will have to wait for contract extension

ESPN’s widely respected senior baseball writer, Buster Olney, says the Yankees will once again opt for arbitration this offseason with their star shortstop, Sir Didi Gregorius. Why? Because of the Bombers’ luxury tax issues.

In a recent Q&A with ‘YGY’ site expert Mike Calendrillo, ESPN’s Buster Olney was asked a number of questions that truly matter, especially when it comes to the contract status of burgeoning Yankees superstar, Didi Gregorius.

MC: Didi Gregorius has been the most complete player in baseball throughout April. Is there any chance the Yankees break from tradition and offer Sir Didi an in-season contract extension, or are the two-sides destined to play out the entirety of Gregorius’ three arbitration years?BO: I think they’ll go through arbitration and the reason why is because any long-term extension that they agree to during the course of the year applies to their luxury tax issue — and as you know, that’s something they’ve worked like crazy to get past.I actually think, that in a vacuum, that if there was no luxury tax penalty hanging above the Yankees, that they would have already agreed to a deal with Gregorius. I do think in the offseason; they’ll probably explore some talks about a multi-year deal.MC: What about the fact that paying Gregorius later as opposed to now, will likely cost the Yankees far more over the life of the deal?BO: The Yankees really covet the flexibility they’re going to have in-season, and they don’t know exactly what’s going to become available to them. It’s one of those rare instances; they don’t usually have this situation where they can choose from the whole menu, between the prospects that they have and the payroll flexibility, when guys become available from other teams, the Yankees will be able to compete for anyone they want.

Did Olney get it right?

Yankees general manager, Brian Cashman has been given absolute control of this team by the Steinbrenner’s, with only one exception and one commandment, “Thou shall not exceed over the luxury tax in 2018.”

George’s boys have always been more interested in the “bottom line” than winning, and Cashman is basking in the glory of his own accomplishments. He brought the Bombers under the luxury tax and put a winning team on the field at the same time.

No doubt about it, Cashman is the greatest GM in Yankees history, and maybe all of baseball. He deserves all the accolades he has received and therefore the control of this team.

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My only problem with Cash is that he is also trying to field manage the club through his self-appointed puppet Aaron Boone. This egotistical mistake will be the only reason for a Yankees’ misstep this season.

When Olney told Calendrillo, “The Yankees really covet the flexibility they’re going to have in-season”,  he was spot on, except maybe a little too politically correct.

I for one think when he says Yankees, he means Brian Cashman. It will be Cashman doing the wheeling and dealing in the trade market to underpin the teams quest for title No. 28.

If the Yanks are not where they are expected to be by the All-Star break due to bubble blowing Boone, and in need of an expensive rental to put them over the top, Cashman will need that flexibility.

Didi Gregorius, no matter what he does this year, will have to wait for another offseason salary dump, unless Cashman can figure a way to do it before. David Robertson, Brett Gardner, Neil Walker, Adam Lind, Adam Warren and C.C. Sabathia may all be gone at the completion of 2018.

That’s about $44 million in payroll.

Next: Let’s not push Brandon Drury out the door just yet

Barring any unforeseen disasters, Sir Didi should be able to cash in this offseason and the Yankees, who have stopped drooling over Manny Machado, will lock up Gregorius to play as a centerpiece for what could be the greatest Yankee dynasty ever.

Buster Olney got it right on the nose.