Yankees Potential Free Agent Target: Gerrit Cole

Much like Captain Ahab devoted his life to chasing Moby Dick, the elusive white whale, Brian Cashman has largely devoted his life to chasing his white whale, front-line starting pitching. Cliff Lee stands out as the most notable one who got away, and that may have cost the Yankees a pennant or two.

This offseason, there’s a new white whale that Cashman is driving hard after: Gerrit Cole. The Yankees have tried—and failed—to bring Cole to the Bronx twice before, and if they want to maximize their championship window, they can’t miss again.

Simply put, Cole is everything that the Yankees need right now. He’s a power pitcher square in his prime with proven big-game experience. The Yankees will have to work to secure his services, as Cole will likely be sought after by at least 10 other teams, and figures to command a record-breaking contract.

Still, he’d be worth whatever it takes, for multiple reasons. For one, Cole is really good! He had the best FIP (2.64) and ERA+ (185) in the league while pitching in an extreme hitter’s ballpark, led the league in strikeouts (326) and posted a stellar K/BB rate (a career-best 6.79). Cole’s dominance, particularly in a year noted for juiced baseballs and a historic offensive output, makes him a commodity that any contender needs to have.

At 29 years old, Cole is very much in his prime and likely still has several years to go at the top of his game. He’s also more than a one-hit wonder. He’s been an All-Star-caliber pitcher for almost his entire seven-year career, and hit another level entirely over the past two years in Houston. He’s a top-three pitcher in baseball, and quite possibly the best right now.

Again, the Yankees have had their chances to acquire Cole, a lifelong Yankees fan, before. The club originally drafted him in the first round in 2008, but he did not sign, and ultimately went first overall to the Pirates three years later.

When Pittsburgh put Cole on the trade block in the 2017 offseason, the Yankees went deep into talks, but ultimately backed off, electing to keep Clint Frazier and Miguel Andujar. Cole went to Houston instead, and has tormented the Yankees ever since. The Yankees have been after Cole for over a decade, and have never been able to actually get him, which has to be weighing on Cashman’s mind heading into what could be his last chance to nab him.

There is some concern and trepidation out there around giving any player, particularly a pitcher, a seven-year deal at over $250 million. However, the Yankees are at the position right now where money has to be no object when the opportunity to seize a championship is at the table. The Yankees’ rotation is one piece shy right now, and what better way to plug that void then by getting arguably the best pitcher in baseball to fill it?

Cole is the big-time pitcher that could instantly put the Yankees over the top as World Series favorites. Other pitchers can make the team better, but only Cole can make them legitimate favorites. It won’t come cheap, and it won’t come without some risk down the line, but I’d argue that a championship or two along the way would make it all worthwhile. Predicting Hal Steinbrenner’s spending habits can be tricky, but if he’s serious about making this team the best version it can be, the 2020 Yankees have to have Gerrit Cole on the roster.