Yankees GM Brian Cashman is unique in many ways. He spends dollars as if they are coming from his wallet. Will that approach prevail in 2020…

The Yankees are so close and yet so far away from that elusive 28th World Championship. It burns inside knowing a player here, a player there, money spent here, money saved there can make the difference from another superlative regular season and the parade down Broadway.

Yankee’s principal owner, Hal Steinbrenner, has hinted he will listen to anything Brian Cashman brings to him, even if it means forfeiting the team’s recent and rigid policy of adhering to the luxury tax payroll threshold (set this year at $208 million).

But the hard truth for Yankees fans who still recall the free-spending days of father George is that Brian Cashman wholeheartedly buys into the practice of fiscal restraint if the alternative is to spend money for the sake of spending money.

Brian Cashman: The Scrooge of New York

Yankee fans stood by helplessly as Cashman refused to budge at last year’s trade deadline, arguing (basically) there’s no starting pitcher out there worth the cost of what it would take to acquire them.

With another postseason failure behind his team, a legitimate question (then) is whether or not Cashman has moved the bar, and is ready to redirect team strategy into a more free-spending mode.

Certainly, the pickings are out there if the Yankees choose to go big. Gerrit Cole, for instance, automatically installs the team as favorites to win the World Series in Las Vegas. Stephen Strasburg isn’t so bad, either.

There’s no doubt the Yankees will be in on the bidding for these and other elite free agents. But, and it’s a big but – will Brian Cashman re-engage after the Yankees make their offer?

Cashman, you’ll recall, made what he considered to be a fair offer to Dallas Keuchel in mid-summer. The Atlanta Braves, we’ll assume, made a better offer and that’s where he played out the second half of the 2019 season.

The same scenario was seen during last winter’s bidding for Patrick Corbin. On behalf of the Yankees, Cashman offered a five-year deal only to be topped by the Nationals who gave Corbin an extra year. Dollar terms between the two deals are unknown, but Cashman held firm, not entering a counter-offer.

Yankees and Cashman: A message to Gerrit Cole et. al.

The inference is clear. And even if touched with a bit of arrogance, Brian Cashman has a message to all free agents, paraphrasing:

“We are the New York Yankees. We would love to have you as part of our team. If you would like to tell your grandkids that you pitched a postseason game wearing the Pinstripes at Yankee Stadium, this your chance. Here’s our offer – it’s a fair and competitive offer – you decide – take it or leave it.”

How that approach sits with Yankees fans is an open question. Fiscal restraint is not supposed to be in the Yankee’s dictionary. The franchise prints money, so what’s the problem?

But that’s the point, which is that Brian Cashman sees another way to achieve the same goal. For instance, here’s how Cashman described Deivi Garcia as a starter prepped for the Yankees in 2020 from their farm system…

“Amazing,” Yankees general manager Brian Cashman said, according to NJ.com, when asked how to describe Garcia’s season just before the start of the ALCS. Garcia on the heels of Domingo German – and maybe Cashman has something here.

The Yankees window to win is wide open

Cashman, like anyone else, reserves the right to change his mind. But it’s not like this is a do or die year for the Yankees, as it was for the aging Washington Nationals in 2019.

The Yankees will be a force to be reckoned with for at least the next six to eight years, with or without Gerrit Cole or Mookie Betts. Aaron Judge, Gleyber Torres, and one of these days, Gary Sanchez form the backbone of the team’s offense.

Luis Severino, German, James Paxton, and a still very young Masahiro Tanaka (31) are formidable – if the Yankees can overcome their inability to hit with runners in scoring position in the postseason.

Whichever way Brian Cashman takes the Yankees as they prepare for the 2020 season, there’ll be no argument coming from here. It’s not a question of money. The Yankees have plenty of that.

But go back and ask the Phillies (Bryce Harper) or the Padres (Manny Machado) how they feel after “winning” the free-agent sweepstakes last winter…

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