The Yankees tried to spin their latest playoff knockout. After losing in six games in the American League Championship Series — the third time in five seasons that the Houston Astros had ushered them off the stage — they insisted they had been strong enough to win.
“Was this roster championship-caliber?” General Manager Brian Cashman said a few days after the loss, which sent the World Series elsewhere for the 10th October in a row. “The answer to that is yes, and I’m not going to lose sight of that in my discussions with ownership and my recommendation of where we need to continue to go.”
Cashman never wants to seem desperate; it is the worst kind of negotiating position, and besides, the Yankees have won 100 games in consecutive seasons. With a few more timely hits in October, they could have won the pennant.
But Yankees fans do not want to hear about 100-win seasons that end without a parade. They remember being shut down by other people’s aces: Dallas Keuchel in 2015, Justin Verlander in 2017, Gerrit Cole in 2019. It is past time to get a lockdown ace of their own.
The Yankees seem to recognize this urgency in their courtship of Cole, 29, the free-agent right-hander who went 24-6 with a 2.39 earned run average and 373 strikeouts last year, postseason included. This is their third pursuit of him, in three different forums, and the setting in which they probably have the most control and the best chance of success.
They drafted Cole in the first round in 2008, but were told that no amount of money could sway him from enrolling at U.C.L.A. They made a trade offer to the Pittsburgh Pirates for Cole before the 2018 season, but when they held on to third baseman Miguel Andujar, the Pirates chose the Astros’ offer instead.
Now, in free agency, the Yankees are trying again. They have met with Cole in California, where he lives, and introduced him to several people who could preview his life in pinstripes: Cashman; Michael Fishman, the data-savvy assistant general manager; Matt Blake, the new pitching coach; and Andy Pettitte, the five-time Yankees champion (and former Astro) who thrived in the Bronx spotlight.
Cole’s affection for the Yankees is well-known. During the 2001 World Series in Arizona, The Star-Ledger ran a photo of him, at age 11, holding a sign that said: “Yankee Fan Today Tomorrow Forever.” This June, Cole giddily watched the Yankees’ Old-Timers Game from the top step of the visiting Astros’ dugout. He beamed after meeting Chris Chambliss — “A U.C.L.A. Yankee!” he said.
While the allure of the Bruins kept the Yankees from signing Cole out of high school, they have long viewed the drafting of Cole as a long-term, long-shot investment, because they began to forge a bond and parted on good terms. Cashman alluded to this when he spoke to reporters on Friday in Stamford, Conn., before his annual practice run rappelling down the Landmark Building as part of the city’s holiday festival.
“Various members of our franchise — Damon Oppenheimer is our scouting director still; him and a number of our staff members — they got a chance to know Gerrit Cole because we drafted him way back when,” Cashman said. “So some of our people know Gerrit Cole already on a personal level, him and his parents.”
Cashman also said, predictably, that the Yankees enjoyed their meetings with Cole and Stephen Strasburg, another elite free-agent starter represented by Scott Boras.
“You see how they carve lineups up, but you never get a chance to know better the person,” Cashman said. “So in both those cases they’re really good, genuine people, good family people, so despite their competitive nature when they have the ball on the mound every five days, you walk away realizing that they would fit in anybody’s clubhouse in a real positive way.”
Niceties and comfort are necessary factors in free agency, but the highest bid almost always matters most. The Yankees understand that signing Cole will require more than the largest guarantee ever given to a pitcher — David Price’s $217 million deal with the Boston Red Sox before the 2016 season — and possibly more than Zack Greinke’s record $34.4 average annual salary for a pitcher.
Their primary competition seems to be the teams closest to Cole’s home: the Angels, who play about five miles from Cole’s high school in Orange, Calif., and the Dodgers. Cole has told the Yankees that geography is a factor, but not a deal breaker. The true difference maker most likely will be the desperation of the teams involved.
The Dodgers have not won the World Series since 1988, but they already have the majors’ best pitching staff (a league-low 3.37 E.R.A. last season) and may have a greater need for another Boras client, third baseman Anthony Rendon.
The Angels have hired a prominent new manager, Joe Maddon, after a devastating season in which the pitcher Tyler Skaggs died of a drug overdose in July, with team officials reportedly already aware of his drug abuse. The Angels have baseball’s best player, Mike Trout, but have not won a playoff game in his eight-year career. Last season, they didn’t have a single pitcher who made 20 starts.
The Angels also have a general manager — Billy Eppler, a former Cashman protégé — whose contract expires after 2020 and an owner, Arte Moreno, who has overwhelmed free agents with huge offers before. But will the folly of his deals for Albert Pujols (10 years, $240 million) and Josh Hamilton (five years, $125 million) hold Moreno back this time?
The Yankees must hope so, because their own motivation is obvious. A rotation of Cole, Masahiro Tanaka, Luis Severino and James Paxton, supported by a dominant bullpen and a powerful lineup, could tilt the A.L.’s balance of power away from Houston and to New York at last.
After a lackluster middle of this decade, the Yankees have grown their farm system, taken control of their payroll (relatively speaking) and resumed their annual visits to the postseason. Now comes the next move, the kind that has worked for them with Catfish Hunter and Reggie Jackson in the 1970s and C.C. Sabathia and Mark Teixeira in 2009: the bold free-agent grab that tells their roster and their rivals that the Yankees are really, truly all in.
James Wagner contributed reporting.