As noted above, the Nationals gave World Series MVP Stephen Strasburg a record-setting contract on Monday. It seems certain that Cole will top that mark, and Tuesday, ESPN’s Buster Olney reported the Yankees have offered Cole a contract larger than the seven years/5 million received by Strasburg. We have more on that here.
As the 2019 Winter Meetings opened in San Diego on Monday, the Washington Nationals re-signed 2019 World Series MVP Stephen Strasburg to a seven-year, 5 million deal. The record-breaking contract gives Strasburg the highest average annual value and the most money for a pitcher in MLB history. His record likely will not stand for too long. Gerrit Cole remains a free agent and will almost certainly topple both of Strasburg’s marks whenever he signs a new contract. 

Boras: Deal could be done in ‘short term’

With Strasburg in agreement with Washington, even more attention has shifted to Cole, who could land with a new team before the Winter Meetings wrap up on Thursday. We’ll keep track of the latest rumors surrounding the 29-year-old flame-throwing righty in this post. Here’s the latest on Cole:
While agent Scott Boras, who represents Gerrit Cole, famously likes to drag out the free agencies of some of his top clients — including Bryce Harper’s last winter — the Cole sweepstakes could be over before too long. Speaking to reporters at his annual Winter Meetings media scrum, Boras said that Cole could sign a deal “in the short term.”

Yankees’ offer tops Strasburg deal

In their pursuit of Cole, the Yankees are looking to trade left-hander J.A. Happ in an effort to clear payroll space to sign Cole. Happ, 37, is owed million next season with a option for 2021 that will vest with 27 starts or 165 innings in 2020. Clearing Happ’s salary space would certainly make the Yankees bid for Cole more manageable, but the Yankees would likely need to attach another player in order for a trade to happen.

‘Mystery team’ in on the Cole bidding

Tuesday night, MLB Network’s Jon Heyman reported that the bidding for Cole was heating up and a deal had a “strong likelihood” of getting done at the Winter Meetings, which wrap up Thursday. Heyman also noted the Angels, Dodgers and Yankees were the leaders for Cole and it was unlikely that he’d land elsewhere.

Yankees shopping Happ to make payroll space

While it’s widely known that the Yankees and Angels (and, to a lesser extent, the Dodgers) are Cole’s main suitors this offseason, MLB Network’s Jon Heyman reports that there is also a mystery team involved and Scott Boras said there are two mystery teams in the mix for his client. As Heyman notes, it is difficult to imagine another team coming in to the sweepstakes and managing to enter a winning bid. But it remains a possibility. One of the mystery teams is reportedly the Astros. We took a look at the other possibilities here.

Yankees to make ‘competitive’ offer

New York Post’s Joel Sherman reports that Yankees general manager Brian Cashman was set to arrive in San Diego at the Winter Meetings on Monday. Sherman adds that the club’s plan was to submit a formal bid for Cole on Monday. It was reported Sunday by Bob Klapisch of the New York Times that the Yankees were set to make Cole a seven-year, 5 million offer (the exact contract Strasburg signed Monday). YES Network’s Jack Curry is also reporting that the Yankees and Cashman are expected to make a “very, very competitive offer” to Cole on Monday.