Gerrit Cole of the Houston Astros pitches during Game 3...

Gerrit Cole of the Houston Astros pitches during Game 3 of the ALCS against the Yankees on Tuesday, Oct. 15, 2019. Credit: Jim McIsaac

SAN DIEGO – Last winter the Yankees never made a bid on the two biggest names atop the free-agent board, angering a sizable number of their fans.  

There was plenty of noise  linking the Yankees to Bryce Harper and Manny Machado, but that’s all it was.

This offseason?

They’re unquestionably in on the top free agents in the marketplace, Gerrit Cole and Stephen Strasburg, and the topic of just how in they are – meaning dollars – will dominate this week’s winter meetings, which start Sunday at the Hilton San Diego Bayfront.

Particularly when it comes to Cole, who has emerged as the club’s No. 1 target, with the full backing of managing general partner Hal Steinbrenner.

“I’m not here to talk finances,” Brian Cashman said in Stamford, Connecticut, on Friday morning during his annual participation in Stamford's Heights & Lights holiday event. “All I can tell you is the obvious. Of course we’re interested in players of this level.”

Evidence of that occurred Tuesday and Wednesday, when Cashman brought a contingent that included manager Aaron Boone, new pitching coach Matt Blake, assistant general manager Mike Fishman and special adviser Andy Pettitte to California for separate meetings with Cole and Strasburg, who both reside there. The group met with Cole on Tuesday and Strasburg on Wednesday.

The Yankees did not make those kinds of efforts last offseason with the marquee names. They never met with Harper, and although they did meet with Machado, it was at the request of the player, who still had to come to them in New York.

There is a different vibe this offseason, and it starts at the top with Steinbrenner.

To be clear: Cashman doesn’t make his trek to California without the go-ahead from the owner that he’s open to considering the kind of monstrous contract it will take to land one of the two aces, the type of contract Steinbrenner has mostly steered clear of in recent years.

Which is not a guarantee the Yankees will get either pitcher.  

The Yankees already have roughly $212 million committed for their 2020 payroll, a figure that puts them over the first luxury-tax threshold. The second threshold is $228 million, which the Yankees are likely to surpass regardless of whether they sign a top free agent. The third tax threshold is $248 million, a level that several club insiders say Steinbrenner would prefer to stay under. He no longer is an absolutist on the matter, though.  

“It’s a big deal,” Steinbrenner said of the third tax threshold in an interview with the YES Network that aired last week. “It’s something we’d certainly prefer not to do, because there are June draft ramifications, there are numerous ramifications. But that is something that I would consider.”

It's something he’s strongly considering, those same insiders say, a sea change even within the last couple of months.

The industry expectation all along has been that World Series MVP Strasburg, 31, who went 18-6 with a 3.32 ERA in the regular season, will end up back with the Nationals. There is less certainty regarding Cole, 29, who went 20-5 with a 2.50 ERA last season and was the runner-up to Astros teammate Justin Verlander in the American League Cy Young Award voting.

It has long been speculated that Cole’s hometown Angels and the close-to-his-hometown Dodgers were the heavy favorites to sign him, but the Yankees, who stressed in their meeting with the pitcher their history of success and the legacy that could be his if he contributes to another World Series title – or more – for the franchise, have the financial muscle to outbid any team if they choose to do so.  

And when all of the mostly meaningless verbiage about hometowns and preferred geography gets stripped away, these things about 99 percent of the time come down to who offers the most money.

Especially for those represented by Scott Boras, as Cole and Strasburg are.

The Yankees have a boatload of that; it’s simply a matter of how much Steinbrenner green-lights Cashman to offer in a sweepstakes that may well end with Cole among the highest- paid players – if not the highest-paid player – in the game.

“I’m not going to talk about anybody in particular,” Steinbrenner said during the YES interview. “But let me just say that all options are open as far as I’m concerned. Anything that rolls along across my desk, I will be looking at real seriously.”

Just how seriously should begin taking shape this week. 

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