Why the Yankees Had to Sign Gerrit Cole

The time was right for the Evil Empire to flex its might.

SAN DIEGO — Never before have we seen a deal like this.

The Yankees and Gerrit Cole agreed to a record-setting nine-year, $324 million contract late Tuesday night, giving New York the top available free agent and upgrading the team’s one weakness from a year ago: the starting rotation.

In an age when teams are relying on their starters less than at any time in the sport’s history, especially pitchers in their mid-to-late 30s, the 29-year-old Cole became the first pitcher to sign for more than $300 million (the fifth player overall). His $36 million average annual value is the highest for any player in the history of the game. Even Mike Trout and his $426.5 million contract isn’t worth as much per year.

By reputation alone, Cole going to the Yankees for this much money seems like a no-brainer. Even before you look at how desperately they needed a true No. 1 starter, justifying this signing with because they’re the Yankees would probably be a satisfactory explanation. Add in the fact that they drafted him out of high school in 2008, only for him to take his scholarship and play at UCLA instead, and that they missed out on getting him from the Pirates in a trade before Pittsburgh dealt him to the Astros in January 2018, and it makes even more sense that the mighty Yanks would be the ones to give him such a lucrative contract.

However, only in name is this the same organization that George Steinbrenner ran for decades, using millions of dollars as bandaids to tend their wounds. In those days, nothing cured a disappointing season quite like a blank check to an established veteran.

Instead, the Yankees of today are run by the Boss’s son, Hal, and general manager Brian Cashman. Over the last five-plus years, the Yankees have been much more prudent with their fortune, embracing analytics and recognizing the value of drafting, acquiring and developing young talent. When Bryce Harper and Manny Machado hit the open market last offseason, the Yankees decided neither player was worth flexing their financial muscles over. The same thing with Yu Darvish and Jake Arrieta the year before that. And in the 2015-16 offseason, they resisted the urge to get into a bidding war with the Red Sox for David Price, who signed with Boston for seven years and $217 million. Fiscal restraint became an important asset.

But, at the same time, this is still the Evil Empire, a franchise more than capable of extending an overwhelming offer when the time is right. That’s what they did following their resurgent 2017 campaign, when they acquired Giancarlo Stanton from the Marlins and agreed to pay $265 million of the $295 million Miami owed him. It’s what they did when they signed Aroldis Chapman in the 2016 offseason, even after they traded him to the Cubs that July. (Whether they should have re-signed Chapman after his domestic violence suspension is a different debate). And going back to the 2008-09 offseason, that’s what they did when they made the franchise-altering decision to sign CC Sabathia to a seven-year, $161 million deal. That winter they also signed first baseman Mark Teixeira (eight years, $180 million) and A.J. Burnett (five years, $82.5 million). Less than a year later, they were celebrating their 27th World Series title in the first year of the new Yankee Stadium.

Similar to the 2008-09 offseason—when they were coming off the first season they didn’t make the playoffs since 1993—the Yankees of today are under a lot of pressure. The 2010s were the first decade since the 1910s that New York failed to win a single American League pennant.

Quite simply, they needed to make a significant move that would give them their best chance to ensure they don’t go the next decade without winning the World Series.

So why Cole, and not, say, Madison Bumgarner or Hyun-jin Ryu? Why did it have to be Cole?

For one thing, he’s probably the best pitcher in baseball, at least he was over the final five months of the season. He’s not yet 30 years old and has no history of arm trouble. But also, just look at the best possible free-agent pitchers over the next four years: Luis Castillo, Noah Syndergaard, Jose Berrios, James Paxton. None of them alone could boost the Yankees’ chances of winning quite like Cole does.

And the Yankees definitely are in a position to win, and considering how difficult it’s been to win consistently over the last two decades—no team has won a World Series in consecutive seasons since the 1998-2000 Yankees—there’s no telling how long their window of contention will stay open. Look at all the young, affordable talent on their roster right now. In their first year of arbitration, Aaron Judge and Gary Sanchez will both make less than $10 million in 2020, well below market value; Gleyber Torres, Luke Voit and Miguel Andujar each will make less than a million dollars next season. All of them are under team control for at least three more years.

But they won’t be able to keep all of them. The faces of the Yankees today won’t be wearing pinstripes forever. The Baby Bombers will grow up, and who knows how good the next generation will be?

The time to win for the Yankees is now. And there was nobody available who gives them a better chance to win than Gerrit Cole.