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Yankees 2019 Winter Meetings Rumors: Gerrit Cole free agency nears “finish line”

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What will day two of the Winter Meetings bring?

MLB: World Series-Washington Nationals at Houston Astros Erik Williams-USA TODAY Sports

Yesterday brought a record contract for a pitcher. Anyone else think that can happen again today? The Yankees will certainly try. We’re going to keep tabs on all the rumors from the second full day of the Winter Meetings, so check back frequently for live updates.

Since it can sometimes be hard to keep up with the news, Pinstripe Alley is going to run a series of posts containing all the Yankees rumors over the next three days. It’s important to remember that these are rumors, and should be taken with a grain of salt. Teams and agents posture, selectively releasing information in a way that benefits them.

Rumors of the Day (December 10, 2019)

  • 11:05 PM ET: Buckle up, friends. the Gerrit Cole saga is drawing to a close. Jon Heyman says Cole’s free agency is “heading toward the finish line.” The Dodgers have also upped their interest and find themselves right in the mix.
  • 6:45 PM ET: Bryan Hoch has a few quotes from Brian Cashman, and they don’t sound promising. Cashman stated that the Yankees have put forth a “championship-caliber effort” to sign Gerrit Cole, but that “Unfortunately, there’s a lot of other quality franchises that are doing the same thing”. This doesn’t sound like a man confident that he’s about to sign the top player on the market.
  • 6:25 PM ET: This here isn’t a rumor, it’s cold-hard news: Didi Gregorius has signed with the Phillies, per Joel Sherman. The former Yankee shortstop will reunite with Joe Girardi in Philadelphia. Reports indicate the deal is for just one year, giving Gregorius a chance to reestablish his value before hitting the market again next year.
  • 3:20 PM ET: Scott Boras held his annual Sermon on the Mount, and he discussed a number of points related to the Yankees. He indicated that Cole’s free agency could wrap “in the short term”, and the Yankees “did a great job” in the process. He also declined to speak on the Jacoby Ellsbury situation, citing it’s a union situation. All updates courtesy of Bryan Hoch.
  • 1:05 PM ET: Jon Heyman has thrown another twist into the Gerrit Cole saga, reporting that there’s a “mystery team” on Cole. Could there really be a team other than the Yankees, Angels, or Dodgers that’s competing for Cole? Could the Astros be trying to re-sign their seemingly erstwhile ace?
  • 12:45 PM ET: Andy Martino relays that the trade market for J.A. Happ consists of a number of NL teams, including the Milwaukee Brewers. A reunion with the Blue Jays isn’t out of the question, either.
  • 10:55 AM ET: It appears the Yankees have officially made an offer to Gerrit Cole. Jon Heyman reports that the team submitted an offer last night, but notes that there “seems to be negotiating to do”, and that the Angels and Dodgers remain contenders.
  • 8:00 AM ET: Scott Boras will address the media at 3 PM ET, according to multiple reports. He will talk about his remaining free agents—including Gerrit Cole—and the landscape of the offseason.
  • 8:00 AM ET: According to George King, the Yankees are making progress on a contract with Brett Gardner. Representatives for Gardner and Brian Cashman have a chance to meet face-to-face, and from there a deal could wrap up quickly.
  • 8:00 AM ET: Add the Milwaukee Brewers to the list of teams interested in Didi Gregorius, says Robert Murray. Yesterday we learned the shortstop may look to reestablish value on a one-year deal.
  • 8:00 AM ET: Remember Gosuke Katoh? The Yankees’ second-round pick in the 2013 MLB Draft has apparently signed a minor-league deal with the Marlins.

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