Gerrit Cole Seeking Massive Free Agent Contract

9:40pm: The Angels and Boras “have had multiple ’ownership-level’ meetings” regarding Cole, Jeff Fletcher of the Orange County Register writes.

6:53pm: Yankees general manager Brian Cashman is “coming with the offer for Cole today,” Heyman tweets. Bob Klapisch of the New York Times reported over the weekend (link below) that New York was preparing a seven-year, $245MM proposal.

5:28pm: Expectations are that Cole will indeed go past the $300MM mark, per the New York Post’s Joel Sherman, who names nine years and $324MM as “not a bad over/under” for Cole’s next deal.

3:13pm: After securing a stunning, $245MM deal for Stephen Strasburg, Boras is on the hunt for an even larger-than-expected payday for Cole.

The goal is for a nine or ten-year pact, per Heyman (via Twitter). The $300MM level “is well within reach,” per the report, with even greater earnings “certainly possible” at this point.

It is believed that the bidding on Cole will come to a head in the coming days, MLB.com’s Jon Morosi tweets. That could set the stage for an old-fashioned Winter Meetings auction of the kind we haven’t seen in some time.

1:07pm: Free agent ace Gerrit Cole continues to be the center of attention as the game of baseball gathers up in San Diego for the Winter Meetings. We’ve yet to seen any seismic news with respect to his market situation, but there’s good reason to believe we’ll see significant developments in the coming days.

Cole’s agent, Scott Boras, informed teams that his client would like to consider offers beginning right away, The Athletic’s Jayson Stark writes (subscription link). The hurler “has been aggressively involved in setting the timing of these talks,” writes Stark, and it seems he’s not interested in a protracted courtship.

While Cole isn’t looking to drag this process out for the next several months, he’s not going to limit his options at the outset. While some geographical preference had been anticipated — Cole, as you’ve no doubt heard, has deep ties to California — it has become increasingly clear that he won’t restrict himself to one coast.

The word now is that Cole “will go with the best value/deal regardless of geography,” Jon Heyman of MLB Network tweets. That certainly leaves the door wide open for the Yankees, who are reportedly preparing to put a big number in front of Cole, but it’s far from a done deal. It’s rumored that the Angels, Dodgers, Phillies, and Rangers are also in the hunt and it remains to be seen which team will separate itself from the pack.

With big-budget organizations pushing hard for Cole, the industry chatter continues to buzz with the likelihood of a record-setting deal. The only question seems to be just how many contractual records will be knocked over and to what extent, as Stark writes. MLBTR predicted a $256MM contract entering the offseason.