The last time the Yankees spent big for free agents, when they spent what used to be known as “Yankee money," was after the 2008 season. New York had missed the playoffs in a full season for the first time in 15 years, eight years after its last World Series title under Joe Torre. Brian Cashman then went out and got the ace pitcher he needed, CC Sabathia, and when Cashman was done spending that winter, he’d invested $423 million in contracts for Sabathia, Mark Teixeira and A.J. Burnett.

The Yankees won the Series in 2009 and afterward Cashman, when asked about the money he’d spent, said, “You can call us whatever you want. But you’re going to have to call us world champions.”

Last time he got to make that statement.

• Gerrit Cole rumors

Cashman wouldn’t have been able to say it without Sabathia, the last true October ace the Yankees had. Masahiro Tanaka has had his moments in the postseason. So have some others. But since Sabathia, the Yankees have not had someone who was expected to pitch the kind of October game that Justin Verlander pitched against them, and for the Astros, in the postseason of 2017. They haven’t had the kind of ace David Price finally became in October, and for the Red Sox, in 2018. They didn’t have someone to stand out there, and stand up, the way Stephen Strasburg and Max Scherzer just did for the Nationals.

And the way Gerrit Cole did for the Astros before he had to sit and watch Strasburg and Scherzer in Games 6 and 7 of the 2019 World Series after Cole’s season was done.

Now Cole and Strasburg are on the free-agent market. No one seems to believe that Strasburg will end up a Yankee, and an awful lot of people seem to think he’s going to stay with the Nationals in the end. Strasburg is 31. Cole, coming off the season of his life, is 29 years old. Sabathia turned 29 during his first season with the Yankees. There have been other star starting pitchers under the age of 30 to hit the market the way Cole does. But Cole is the one who is in play now.

There was no better, stronger starter in the sport last season, whether Verlander beat him out of the Cy Young Award or not. The Yankees don’t just want Cole. They need Cole the way they needed CC. The Yankees were eight years removed from a trip up the Canyon of Heroes when CC hit town. Now it is 10 years, not just without a World Series for the Yankees but without even making it that far.

I asked Cashman the other day if he thought the Yankees had a realistic shot at Cole.

The answer, by text, was this: “Idk.”

What he does know, of course, and the way people in outer space know by now, is that the Yankees drafted Cole out of high school -- and were prepared to offer him a lot of money at the time -- but instead watched him go play college baseball at UCLA. When the Pirates were ready to trade Cole in 2018, it was the Astros who got him and not the Yankees.

In the last 10 years, and since the last World Series, the Yankees did spend over $150 million on Tanaka, when he left Japan. They also spent that much on Jacoby Ellsbury, whom they just released. When Scherzer was a free agent, the Nationals got him. When Verlander ended up being traded by the Tigers in the summer of 2017, the Astros were willing to take on the rest of Verlander’s Tiger contract at the time. The Yankees had a budget at the time that Cashman was not allowed to exceed. Patrick Corbin was a free agent last winter after leaving the D-backs. Corbin was terrific in Arizona, if not in the same elite class as Verlander/Cole/Scherzer/Strasburg. The Nationals ended up out-bidding the Yankees on Corbin, who turned out to be an essential No. 3 starter for the World Series champions.

Now here the Yankees are with Cole. He’s the most elite starting pitcher out there. In his prime. Coming off the season of his life. Somebody who doesn’t turn 30 until next September. Jon Lester was 30 when the Cubs signed him to a big free-agent contract before the 2015 season. The next year the Cubs ended 108 years of waiting for a World Series title. When they were down three games to one to the Indians in the ’16 World Series, Lester got the ball. And the win in a 3-2 game. He was That Guy when the Cubs most needed him to be. He was everything an ace is supposed to be.

The Yankees never have a losing season. They are now a decade without a World Series. They do so much right at Yankee Stadium. But starting pitching continues to be an issue. You can make the case that the previous starting pitcher from their farm system to last was Andy Pettitte. They’ve got young guys now. Luis Severino has a world of promise. There are other kids for whom they have high hopes. They truly haven’t developed anybody like Pettitte since Pettitte.

And they haven’t signed a free agent as talented as Sabathia since Sabathia. All respect to Tanaka, but the most victories he’s ever had as a Yankee are 14. He has never been That Guy. Cole is That Guy. Guys like that don’t come around often. No one knows that better than the general manager of the Yankees, looking for a stocking full of Cole this Christmas.