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Yanks arrive at Meetings with eyes on Cole

@BryanHoch
December 9, 2019

SAN DIEGO -- The richest deal ever handed to a free agent pitcher in terms of total dollars and average annual value was handed out on Monday, with Stephen Strasburg and the Nationals shaking hands on a seven-year, $245 million pact. If the Yankees have their way, those are records

SAN DIEGO -- The richest deal ever handed to a free agent pitcher in terms of total dollars and average annual value was handed out on Monday, with Stephen Strasburg and the Nationals shaking hands on a seven-year, $245 million pact. If the Yankees have their way, those are records that will not stand for long.

Strasburg’s landmark agreement has effectively set the bar for what the Yankees will have to offer in order to fit Gerrit Cole for pinstripes, and it is believed that managing general partner Hal Steinbrenner has authorized his baseball operations team to continue their full-court press for the coveted right-hander.

“There's a lot of great players out there, Cole included,” Cashman said on Sunday in Stamford, Conn. “There's always competition for talent. That's the one thing that never changes. … At the end of the day, if you're a free agent, talent gets paid. We understand that and we go into it with our eyes wide open.”

Cashman arrived at the Manchester Grand Hyatt on Monday morning and was expected to present a substantial offer -- potentially one that could stretch beyond eight years and surpass $300 million -- to Cole’s agent, Scott Boras.

Boras, who also represents Strasburg, said that he would prefer to address Cole’s situation in a news conference that will be held on Tuesday. Likewise, Cashman bypassed his usual scheduled Winter Meetings media session, with the Yankees instead sending word that the GM plans to speak to reporters on Tuesday afternoon.

Strasburg’s contract surpassed the $217 million, seven-year deal that David Price received from the Red Sox prior to the 2016 season, while the highest average value had been Zack Greinke’s $34.4 million annual payout as part of a six-year, $206.5 million pact secured with the D-backs prior to the 2016 season.

Cole’s upcoming pact has a chance of creating substantial distance from those numbers. The Angels and Dodgers are also thought to be involved in the bidding for Cole, a Southern California native who attended high school in Orange, Calif., and turned down a first-round Draft selection by the Yankees in 2008 in order to honor his commitment to UCLA.

While those Golden State roots were initially thought to hold sway, recent indications have suggested that Cole intends to accept the most substantial offer, regardless of geography. Cole is also said to be interested in playing for a contender, and having won 203 regular-season games over the past two seasons, that is a selling point that the Yankees can offer over the Angels.

“It's a high bar to try to improve upon what you've already got, because we've got a lot of great players we're really proud of,” Cashman said. “But the job is to try to make it better.”

The 29-year-old Cole has thus far been the great white whale of Cashman’s recent tenure as GM. After watching Cole opt for college, the Yankees had another crack at his services in the winter of 2017-18, when the Pirates dangled him to interested clubs. Cashman balked at including third baseman Miguel Andujar in negotiations, and Pittsburgh ultimately accepted a four-player package from the Astros.

Cole was 35-10 with a 2.68 ERA in 65 starts for Houston over the past two seasons, earning selection as an American League All-Star in both years. He finished second to teammate Justin Verlander in the AL Cy Young Award balloting in 2019, leading the Majors with 326 strikeouts and a 185 ERA+ while finishing 20-5 with a league-leading 2.50 ERA in 33 starts.

Having grown up a Yankees fan in Angels territory, the Bombers attempted to tug on Cole’s nostalgia for the franchise during a visit prior to the Winter Meetings, inviting former pitcher Andy Pettitte to accompany a group that included Cashman, assistant general manager Mike Fishman, manager Aaron Boone and pitching coach Matt Blake.

A potential nine-figure outlay to a free agent starter would be the Yankees’ first since 2014, when Masahiro Tanaka agreed to a seven-year, $155 million pact.

At present, the Yankees’ rotation projects to feature Tanaka, James Paxton, Luis Severino, J.A. Happ, and perhaps Domingo German or Jordan Montgomery. While Cole’s potential deal could push payroll past the third Competitive Balance Tax threshold of $208 million, Steinbrenner is thought to be amenable because Tanaka, Paxton and possibly Happ could all be free agents after 2020.

“Financial components are a factor in every decision we make,” Cashman said. “It's always a part of the process -- revenue sharing and current commitments and tax consequences. All those things are relevant discussion points that you have to have if you're in that category, which we are.”

Aside from their Cole pursuit, Cashman said that the Yankees are multi-tasking with other areas of the roster. A reunion with outfielder Brett Gardner continues to be discussed, with Gardner set to score a substantial raise over the $9.5 million he earned in 2019. The Yankees are also in contact with free agents Dellin Betances, Didi Gregorius and Austin Romine.

“I'd love to get something done yesterday. I don't like dragging it out,” Cashman said. “If you can get your work done sooner than later, you feel more comfortable and sleep better at night.”

Bryan Hoch has covered the Yankees for MLB.com since 2007. Follow him on Twitter @bryanhoch and Facebook.