In a very unlike “Yankees” statement, Hal Steinbrenner indicated there is no sense of urgency for the team’s 28th World Championship. Did he misspeak?
Chief Operating Officer of the Yankees, Hal Steinbrenner, is generally not a high profile owner. So, the 40-minute phone conversation he had with Joel Sherman of the New York Post represented an opportunity to peek inside his mind a bit. What’s revealed is as surprising as it is perplexing:
The Yankees, you’ll recall, had “a number of good years coming” in 2016 with the birth of the Baby Bombers. Three seasons later, the Yankees have yet to close the sale on a World Series title. Even Steinbrenner himself said he was “pissed off” about the Red Sox easily beating the Yankees in the playoffs, giving pause to wonder if the idea behind the Baby Bombers has evolved merely into a myth.
And yet, as though nudged by his Dad from the grave, Hal Steinbrenner rebounds with a more Yankees-like statement:
So, which is it? If this were Fred Wilpon, the owner of the dysfunctional New York Mets talking, we would better understand and be able to translate double-talk when we hear it. Unlike Wilpon, who has pre-determined that the Mets are not in a re-build mode, and are in it to win it with their big-three starting pitchers, Steinbrenner appears to be still trying to figure things out for his Yankees.

Enter Brian Cashman, carrying the title of a former General Manager of the Year. The man who has the ear of Hal Steinbrenner like no one else. The man who can sway Steinbrenner one way or the other provided Cashman can make the case either way.
Stay pat, fill in a few holes a la Jonathan Corbin, re-sign CC Sabathia and David Robertson, percolate the young talent in the farm system like Justus Sheffield and Estovan Florial for another year, and still the Yankees will have enough talent to make the playoffs with one hand tied behind their back if they need to, all while staying under the luxury tax payroll threshold of $206 million.
Or, present the case to Steinbrenner that adding another elite status free agent to the payroll, and paying the tax in return for a real shot at the Red Sox and a World Title in 2019 is money well spent, and the way your Dad would be thinking too.
But it’ll take more than that to perk the interest of Steinbrenner in a Manny Machado (please no) or Bryce Harper (lukewarm yes) because Hal Steinbrenner is no dummy, and he can see the mistakes his Dad made with long-term contracts to Mark Teixeria and Alex Rodriguez, and how they crippled the Yankees at the back-end of those contracts.
Cashman is well aware of the albatross contained in the contract he took on when he traded for Giancarlo Stanton, an agreement which will have lasting effects on the Yankees unless Cashman can unload Stanton in a trade.
Steinbrenner has indicated adding either Machado or Harper (with Stanton still on board) is not out of the realm of possibility, essentially telling Cashman, convince me!
Which is why Steinbrenner should be cast among the elite of major league team owners. He’s willing to spend, but he’s also challenging his GM – convince me I’m making a wise investment I can sell to my stockholders.
Thus, the dynamic between Brian Cashman and Hal Steinbrenner is something we want to be attuned to as we enter the offseason. Will Cashman draw a line separating himself from Steinbrenner saying “I want it all now” with a rush into the free agent or trade market, or rest easier under the Steinbrenner dictum, and buying into the “we have a number of good years coming”?
I’m thinking Steinbrenner only rationalizing when he tags the Yankees as a franchise looking at “good years coming,” and the sting of the Red Sox will open the checkbook because he’s not the only one “pissed off.” Filled with intrigue, for now, the proverbial ball remains in Cashman’s court.