The Yankees offseason takes a big step forward this week. According to The Athletic‘s Ken Rosenthal and the New York Post‘s Joel Sherman, the team will meet with elite free agent pitchers Gerrit Cole and Stephen Strasburg today and tomorrow, respectively, in California.

Sherman reports the Yankees have sent a contingent of general manager Brian Cashman, manager Aaron Boone and new pitching coach Matt Blake out west to meet with the two players widely considered to be the top two free agents.

This is a stark change in strategy from last year’s pursuit of lefty Patrick Corbin, who the Yankees invited to the Bronx just before he signed his six-year contract with the Washington Nationals.

Cole has been an elusive target for the Yankees, having declined to sign with them in 2008 after being drafted 28th overall in favor of going to UCLA. The Yankees were also unable to acquire him from Pittsburgh prior to the 2018 season, which saw him go to Houston.

The organization has fears that Cole only would like to sign with a team on the West Coast, but that concern also existed before the team landed CC Sabathia prior to the 2009 season. Sabathia, of course, mentioned that he has given his pitch to Cole about being a “West Coast guy” pitching in New York.

However, “the Yankees want Cole more than they’ve wanted a top free agent in years,” reports SNY‘s Andy Martino. That could make the difference in their third pursuit of Cole in 11 years.


I consider myself more intrigued, in a way, by the meeting between the Yankees and Strasburg. The prevailing narrative right after the World Series was that he would opt out of the final four years and $100 million on his original Nationals contract but quickly negotiate a bigger guarantee to stay with Washington.

Then, there were reports that he would consider his hometown San Diego Padres as a possible landing spot. Now, the 31-year-old reigning World Series MVP is meeting with the Yankees and Bob Nightengale of USA Today has linked him to the Los Angeles Dodgers.

What seemed like a mostly open-and-shut free agency for Strasburg has now turned into more of an open forum.


SNY‘s Martino has also mentioned that the Yankees are monitoring the markets of back-up plans like Madison Bumgarner and Zack Wheeler.

Brian Cashman also mentioned the numerous depth options that exist within the Yankees minor-league system, although none of them come close to the potential abilities of Cole or Strasburg.


Make no mistake: this trip by Cashman, Boone and Blake shows how committed the Yankees are to improving the top of their starting rotation. Cashman has his annual rappel down a building in Stamford, Connecticut, on Friday. That means the GM flew out west knowing he’d be back east again before heading to San Diego for the Winter Meetings.

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