Skip to main content

Yankees Winter Meetings Recap

With over $900 million spent, on over 10 different free-agent signings, the 2019 Winter Meetings in San Diego was an exhilarating, exciting and expensive week.

Signing Gerrit Cole was the move that set the Hot Stove ablaze, yet it wasn't the only deal New York made -- nor the only acquisition that involved those that played for the Bronx Bombers this past season. 

If you're feeling nostalgic from an electric week of rumors, breaking news and talented ballplayers getting paid -- or just need a quick refresher on what went down -- here's a recap of every deal involving the Yankees from the Winter Meetings:

Stephen Strasburg, Washington Nationals

Seven-years, $245 million

It never felt like Strasburg to the Yankees would come to fruition, as Gerrit Cole was always the club's priority, but New York was certainly in the running for the reigning WS MVP.

While New York was recruiting Cole, flying cross-country to meet with the free-agent hurler prior to the beginning of the Winter Meetings, the organization's contingent sat down with Strasburg as well. 

The biggest factor that impacted the Bombers from Strasburg re-upping with Washington, however, was the value of his deal.

Early during the week, Bob Klapisch of the New York Times reported that Cole had a seven-year, $245 million offer on the table from the Yankees. Sound familiar? That's the exact amount Strasburg ended up making.

Agent Scott Boras played this out perfectly from a financial perspective. Getting Strasburg to ink a deal first, while Cole -- valued higher due to his youth, injury history (or lack there of) and his unwavering dominance over the past few seasons -- waited patiently and remained available, made negotiations skyrocket.

Think about it this way. If Cole signed first, for the reported figures, Strasburg would've likely made far less and the Yankees would've paid $79 million fewer for their top offseason target. 

In the days after Strasburg's steep signing, the likelihood of Cole signing before the end of the Winter Meetings increased.

As it turns out, the likelihood was very high...

Gerrit Cole, New York Yankees

Nine-years, $324 million

Mission accomplished. 

The Yankees wanted him badly -- Brian Cashman called the right-hander their 'white whale' after missing out on him twice before -- and New York did everything in their power to get him.

They offered a humongous, record contract, featuring more average annual value ($36) than any other contract in baseball history -- even more than Mike Trout. They indicated their interest by flying cross-country for some extra face time. They even brought along a couple secret weapons that reportedly paid huge dividends in the negotiations process: new analytics-minded pitching coach Matt Blake and former Yankees ace Andy Pettitte.

$324 million is the largest contract ever for a starting pitcher, but he's one of the best pitchers in the game and worth the price to reel him in away from other suitors. 

Didi Gregorius, Philadelphia Phillies

One-year, $14 million

Scroll to Continue


Signing Cole is certainly a reason to celebrate, but saying goodbye to Didi Gregorius had Yankee fans remorseful just one day later. 

Gregorius, who was tasked with filling Derek Jeter's shoes in 2015, quickly grew to be a fan favorite. In five seasons in the Bronx, Didi hit .269 with 97 home runs, 360 RBI and 659 hits (in 660 games).

With 23-year-old Gleyber Torres ready to fill in at shortstop, and quite a bit of money set aside for Cole, the chances of bringing back Gregorius were slim. 

After Tommy John surgery sidelined Gregorius for the majority of 2019 -- and he struggled to get back up to speed once he returned to the field -- signing a one-year deal gives Didi a shot to bet on himself and build up his value, seeking a long-term contract in 2021. 

Gregorius now reunites with former skipper Joe Girardi in Philadelphia and slots into a talented lineup including Bryce Harper, Rhys Hoskins and J.T. Realmuto.

Brett Gardner, New York Yankees

One-year, $12.5 million

It wasn't if Brett Gardner would re-sign, it was when.

Once negotiations were finalized with Cole, as the gravity and scale of the ace's contract required all of the organization's attention, it was time to bring back the longest-tenured Yankee.

With Aaron Hicks sidelined for the foreseeable future, as he slowly works his way back from Tommy John surgery, Gardner's value in the outfield is indispensable. Not to mention the fact that the 36-year-old had a career year in 2019 -- Gardy set personal bests in home runs (28), RBI (74), SLG (.503) and OPS (.829).

With Gregorius and CC Sabathia's departures, Gardner's presence as a leader is more crucial than ever as well. He's been in pinstripes his entire career -- 12 seasons -- and is the last remaining member of the 2009 World Series Championship Yankees. With lofty expectations and aspirations in 2020, his experience winning a ring over a decade ago will be pivotal in this team's success. 

Even as his impact in the box score wanes, his work in the clubhouse and with the youngest, most inexperienced bunch of Bombers makes this signing a no-brainer. 

Austin Romine, Detroit Tigers

One-year, $4.15 million

The backup backstop baton has officially been passed on to Kyle Higashioka. 

It seemed like New York was leaning toward letting Austin Romine walk this offseason, as Higashioka is out of minor-league options and the organization believes the 29-year-old is ready to increase his role. 

Romine, however, had been with the Yankees for eight years -- he was even drafted by the club in 2007 out of high school. 

It wasn't always flashy, but Romine found a way to get it done. In 2019, backing up Gary Sanchez (who is notorious for finding his way on the injured list) Romine hit .281 in 72 games. 

Further, and similar to Gardner, his presence in the clubhouse was palpable. 

There isn't much to say about Romine's future with Detroit. The Tigers won 47 games in 2019 -- the worst in the league and seven fewer than the lowly Baltimore Orioles. Surely his experience will be welcomed with open arms in his new clubhouse. 

As for New York, questions linger regarding whether or not Higashioka is up for the second-string spot. Another option would be to sign Martin Maldonado, or another one of Gerrit Cole's former backstops that he has had success with. The Yanks have some time before Spring Training to sort that out. 

To keep up with all of Yankee Maven's coverage, click the "follow" button at the top righthand corner of this page. For more from Max Goodman, follow him on Twitter @MaxTGoodman