NY captures the Great White Whale

When Gerrit Cole agreed to a record-shattering nine-year, $324 million contract with the Yankees late on Tuesday, Aaron Boone received the news much the same as the rest of the world. The manager's phone buzzed with a text message, prompting a visit to Twitter. Several of his players shared their late-night glee, with Aaron Judge and Gleyber Torres taking to social media in celebration.

"That's when you knew it looked like it was happening, so I was excited," Boone said on Wednesday. "I had a couple of interactions with players. I think there's some excitement."

That sentence, delivered with a knowing smirk, represents an understatement of massive proportions. By offering a pact that exceeds previous marks in terms of total value for free-agent pitchers and average annual value for any player, general manager Brian Cashman finally landed the pitcher to whom he referred as his "great white whale."

Here are several questions we've entertained in the hours since Cole's decision sent shock waves through the Winter Meetings lobby:

Yep, those numbers are not typos. In terms of dollars given to a free-agent pitcher, Cole's $324 million blew past the seven-year, $245 million deal that Stephen Strasburg signed with the Nationals on Monday. Before this week, David Price's seven-year, $217 million pact with the Red Sox (signed in December 2015) held the high mark.

With an average annual value of $36 million, Cole's deal exceeds the $35.54 million that Mike Trout is bringing in from the Angels.

"Elite players get paid, typically," Cashman said. "If you want to compete for the elite-type talent, you're going to have to step up to the plate and allow yourself to be noticed."

In addition to potentially incurring penalties by exceeding the third luxury tax threshold of $248 million, the Cole signing will force the Yankees to forfeit their second- and fifth-round picks in the 2020 MLB Draft, plus $1 million from their international bonus pool in the 2020-21 signing period.

The deal is not official because Cole still must pass a physical, but that is thought to be a formality. The Yankees said that an announcement will not occur before next week, when they plan to have Cole don the pinstripes at a Yankee Stadium news conference. Cole's uniform number has not yet been announced; Cole wore No. 45 with the Pirates and Astros, but that is currently assigned to Luke Voit. 

Cashman's Great White Whale

Las Vegas didn't waste time adjusting to reflect the Cole signing, with some oddsmakers on the Strip identifying the Yankees as World Series favorites. 

Why? To start, Cole's arrival delivers a 1-2 punch, solidifying the top of the Yankees' rotation while weakening the starting five of the American League champion Astros. The 29-year-old Cole was 20-5 with a league-leading 2.50 ERA (185 ERA+) last season, pacing the Majors with 326 strikeouts and finishing second to teammate Justin Verlander in the AL Cy Young Award voting.

"You are talking about a guy who is the best of the best, in the prime of his career," Boone said. "Any time we can add an impact performer like that, we feel like that potentially brings more than just between the lines. This is the kind of person that you feel like has all the winning intangibles and makeup."

New York's full-court press to sign Cole moved into high gear on Dec. 3, when a contingent that included Cashman, assistant general manager Michael Fishman, Boone, pitching coach Matt Blake and retired hurler Andy Pettitte traveled to Newport Beach, Calif., to meet with Cole and his wife, Amy. Managing general partner Hal Steinbrenner did not attend, but he spoke to Cole via telephone.

The meeting with the Coles and the pitcher's agent, Scott Boras, lasted more than four hours, during which the club attempted to describe what life would be like if they selected the Yankees' offer. The presentation was reminiscent of the one that the team utilized to woo CC Sabathia in December 2008, when they convinced a California product that the Bronx would be the right fit.

Boone strongly believes that having Pettite in the room helped to sway Cole's decision -- after all, who better to express the differences between performing in New York and Houston, and what a Yankees World Series ring can do to cement a legacy?

"I think so much of him," Boone said of Pettitte. "He brings so much to the table. We've started to try and increase his role a little bit with the organization because he does have such a positive impact on guys. When he says something, he connects. It's impactful and I'm confident that was the case when he came with us."

The Yankees believe that Cole's willingness to bet on himself speaks volumes about his character -- he did so as a high school draftee in 2008, bypassing their offer in order to attend UCLA, then turned down extension offers as a big leaguer so he could reach free agency.

On several occasions this week, Boone and Cashman have expressed that they have no doubt Cole will be an instant fit in New York, lauding his intensity and focused mindset.

"Those are examples of someone who's talking the talk and can walk the walk," Cashman said. "They're just little glimpses into the persona. There's no guarantee for anybody on any level, but you try to have your takeaways from the people that coach them and that played alongside of them. Then you see how they react in the crazy environment of playoff baseball and World Series baseball. And listen, he has checked every box thus far."

With the Cole holding pattern lifted, Cashman is free to continue engaging with outfielder Brett Gardner, as both sides aim to continue their productive relationship. Gardner is expected to earn a significant raise over the $9.5 million he earned this past season, and he would provide a capable option in center field with Aaron Hicks (Tommy John surgery) expected to be out until at least June.

Right-hander Dellin Betances and catcher Austin Romine are among the club's other free agents. Cashman has expressed confidence in Kyle Higashioka as a backup to catcher Gary Sanchez, but another option could be free agent Martin Maldonado, who caught Cole 10 times in 2019. In those games, Cole had a 1.57 ERA and .471 opponents' OPS, his lowest numbers with any of Houston's catchers.

Now boasting an impressive rotation headed by Cole, Masahiro Tanaka, James Paxton and Luis Severino, the Yankees are expected to continue shopping left-hander J.A. Happ, though there is no imminent deadline to move the veteran. Happ is set to earn $17 million in 2020, a figure that could offset some of Cole's contract and help the Yanks avoid luxury tax penalties.

 "I've got simultaneous conversations going on," Cashman said. "Everything gets tied together because you don't have unlimited resources, even though our resources are more than most. I am having sidebars all over the place."

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