It was only a matter of time until the Yankees sat down with Gerrit Cole. The free-agent hurler’s meeting with New York prior to the Winter Meetings, however, has meaning.

A group headlined by Brian Cashman, Aaron Boone and new pitching coach Matt Blake flew cross-country to meet with Cole on Tuesday as well as Stephen Strasburg on Wednesday -- as first reported by Ken Rosenthal of the Athletic.

Both aces, represented by Scott Boras, have drawn interest from multiple clubs. While Cole is to choose between his hometown Angels and New York, the team that drafted him out of high school, Strasburg is sure to be torn between a homecoming in San Diego, a return to D.C. to defend the Nationals’ World Series title, or perhaps a trip up to the Bronx.

For New York, although their rotation would likely be strong enough as it is to take them to October, the need to add a starting pitcher this offseason is high on the organization’s to-do list.

Not only are Masahiro Tanaka and James Paxton set to enter free agency next winter, but it remains to be seen how Luis Severino will bounce back from a lost season in 2019 due to a right shoulder injury and Domingo German -- after a breakout season -- faces possible suspension due to a case of domestic violence.

The Yankees haven’t signed a starting pitcher to a nine-figure deal since agreeing to a seven-year, $155 million contract with Tanaka in 2014. In 2008, CC Sabathia signed with New York for a record $161 million over seven seasons. A deal to put Gerrit Cole in pinstripes would certainly exceed those signings monetarily -- the right-hander proved he's worth it in 2019.

So, if the Yanks bringing in a starter this offseason is a logical expectation, what does the discussion with Cole ahead of the Winter Meetings mean? Let’s break it down.

For Cole, New York is willing to go above and beyond. But is it enough?

An initial meeting with Cole can be seen as nothing more than a formality -- that’s how free agency works after all, players and their agents meet with teams in hopes of finding an agreement that works for both sides. This meeting, however, is different.

Cashman flew out to California for some face time with Cole. He also will be in San Diego for next week’s Winter Meetings and will sit down with Cole and his team again. That means, since the Yankees GM is scheduled to rappel down the Landmark Building in Stamford, Connecticut on both Friday and Sunday, Cashman added an additional roundtrip cross-country flight to his schedule this week just to meet with Cole.

Surely Boone could have handled the meeting on his own, right? Alternatively there could have been a phone conversation or the Yanks simply could have notified Cole and Boras that they wouldn’t be meeting in person until the Winter Meetings. Simple enough, and it likely wouldn’t have deterred New York’s shot at signing the three-time All-Star.

Instead, the organization and its general manager made a herculean effort to be there and to make their initial pitch in person. 

Reports from Tuesday’s meeting say it went well and although no financial specifics were discussed, New York made it clear that the money will be there.

In other words, they didn’t feel the need to focus on the dollars and cents -- by simply telling the free-agent that money is no object, they could focus on the factors that will (in their minds) convince Cole to choose the Bronx over a team that plays minutes away from his home.

Does geography outweigh a record contract?

No matter what the Yankees do to prove their interest and attempt to pitch pinstripes to the 29-year-old, Cole may make his decision on a basis of geography. And if he does, the truth is there’s nothing the Yankees can do about it.


Cole grew up a fan of the Angels and let’s be honest, who wouldn’t want to return as an established big leaguer and play for their hometown team (while potentially being paid upwards of $300 million to do it).

New York also holds a special place in Cole’s heart -- he was drafted by the organization out of high school in 2008 and grew up rooting for the Bombers as well. But that could end up as an insignificant footnote.

Cole signing with the Angels is arguably a logistical no-brainer, which must have the Yankees high strung. This is their top target this offseason, and the Yankees can pay him enough so that money is no object, and yet signing him may be out of their control.

Take a look at Zack Wheeler’s decision to sign with the Philadelphia Phillies on Wednesday. 

Wheeler reportedly was offered more money to play for the Chicago White Sox, an up-and-coming contender that made a splash signing free-agent backstop Yasmani Grandal last week. And yet, with more money on the table from the Sox, Wheeler picked Philly in part because it’s closer to where his wife is from in New Jersey.

Chicago did nothing wrong, they offered Wheeler a better deal. In the end, however, he picked a different team and the club is forced to move on to other options.

By meeting with Cole in person this week, prior to additional conversations in the coming days and weeks, it shows the Yankees are willing to do whatever it takes to win him over. The question is, will it be enough?

Bringing Matt Blake along could change the tides

Money and location are important, but we’re forgetting one key component: which team will be the best for Gerrit Cole’s career moving forward.

Cole may not have won the AL Cy Young Award in 2019 but he solidified his reputation as one of the best pitchers in baseball. 

This free agency decision has the potential to be a career-defining choice. Sure, Cole can win individual awards and pitch well no matter what team he chooses, but in terms of winning championships and learning from a top-notch coaching staff, New York may very well be the best option.

Blake was hired to replace Larry Rothschild this offseason as the Bombers pitching coach and brings a modern perspective and philosophy of pitching to the Bronx. He had previously worked his way up in the Cleveland Indians system, a club renowned for the development of young hurlers utilizing analytics and technology.

Meeting with Cashman and Boone adequately provides Cole with a perception of the ‘Yankee Way’ and the organization's legendary history -- both valuable components in bringing in a free-agent. That being said, if Blake is able to articulate to Cole how he plans on keeping him healthy, training him to get better and showcasing his talent at the top of the rotation, it surely will have an impact on Cole’s final decision.

After all, mix a legitimate shot at the franchise’s 28th championship with some of the best and brightest minds in the game assisting with your performance both on and off the field. Sounds pretty tempting, right?

This is no typical free-agent signing. The money attached to a deal with this right-hander and the impact he’ll have on the field makes this a blockbuster acquisition, no matter what team he chooses.

For the Yankees, someday they’ll look back at this initial meeting with Cole and know that regardless of the California native’s decision, they’ll have given it their best shot.

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