New York Yankees general manager Brian Cashman did not mince words Tuesday afternoon at the Winter Meetings. He called Gerrit Cole his “white whale” and said “we’re playing the obvious game” in free agency. The Yankees failed to sign Cole as their first-round pick in 2008, and again failed to acquire him in a trade with the Pirates two years ago. They would not be denied a third time.
It’s not easy to improve a 103-win team but the Yankees did have a glaring need atop their rotation. Cole addresses that weakness emphatically. The money is outrageous, but outrageous talents commands outrageous dollars. It may have taken 11 years, but Cashman and the Yankees finally landed their man Tuesday night. 
Cashman has spent more than a decade chasing after Cole, first as a drafted player and then through trades, and now that he has him, the timing couldn’t be better. Severino, Aaron Judge, Gleyber Torres, and Gary Sanchez are in their primes. The window to win isn’t getting any more open and Cole is a balance of power player. He can swing a postseason race or series by himself.
Unlike 2008 and 2017, Cole was a necessity for the Yankees heading into 2020. The club had missed out on numerous ace-caliber pitchers in recent years, including Justin Verlander at the 2017 trade deadline and Patrick Corbin last offseason, and that left them short in the arms race. New York reemerged as a superpower three seasons ago but has lacked a bona fide ace.
Cole, who rejected his hometown Angels to sign with the Yankees, is on the short list of the game’s elite hurlers and is in the prime of his career at age 29. A decade ago the Yankees gave a record contract — then only seven years and 1 million — to another ace in his late-20s in an effort to get over the hump in October. CC Sabathia led the Yankees to a title in Year 1 of that contract. Late Tuesday night Cole agreed to a massive nine-year contract worth 4 million to become a Yankee, more than 11 years after the team’s courtship began. It is the largest pitching contract in history in terms of total value and annual value, shattering the record set by Stephen Strasburg on Monday. Only Mike Trout, Bryce Harper, and Giancarlo Stanton have signed richer contracts in baseball history.
New York adds Cole to 2019’s highest scoring offense (minus new Phillie Didi Gregorius) and an overpowering bullpen, and depth that borders on obnoxious. Every team lucks into a Gio Urshela now and then. When you do it as often as the Yankees (Urshela, Mike Tauchman, Luke Voit, etc.), it’s a skill, not luck. They’re smart and savvy, and still willing to blow free agents out of the water.
To get Sabathia the Yankees passed on Johan Santana a year prior. It was an incredibly risky move — Sabathia could have signed an extension or gotten hurt — but Sabathia was the pitcher they wanted, and, ultimately, it worked out. Passing on Santana put New York in a position where they were desperate to get Sabathia. Passing on Verlander and Corbin made them desperate for Cole.
Desperation leads to irrationality and irrationality leads to record-breaking contracts. There is nothing rational about giving a pitcher a nine-year contract — Cole’s pact will likely look ugly come 2027-28 — but with front offices having become mind-numbingly pragmatic, a little old school free agent irrationality is almost refreshing. The Yankees were willing to be irrational to get Cole. “Special, special guy. Obviously a great athlete, a great pitcher in the prime of his career,” manager Aaron Boone said Tuesday when asked about last week’s meeting with Cole and Scott Boras.  
The Yankees will now go into next season with Cole, who gets a stamp of approval from scouts and statheads alike, atop the rotation and Luis Severino, James Paxton, and Masahiro Tanaka falling in line behind him. Severino, Paxton, and Tanaka pitched New York to within two wins of the World Series this year. Cole was among those who stood in their way. Now he wears pinstripes