5 biggest free agency and trade misses in modern Yankees history

One move here, one move there. The right ones. If a few others bounce the New York Yankees‘ way (or, you know, they just had decided to spend freely instead of saving the equivalent of $75 for the everyday folk) then we’re probably not talking about a 12-year World Series drought and mounting expectations heading into 2022.

And for the 100th time, we’re not calling the Yankees “cheap.” The payroll is consistently over $200 million. However, when you’re not spending shrewdly and refusing to pay a totally affordable tax penalty to make up for some bad decisions while making more revenue than ever, there’s plenty of criticism to go around.

Don’t believe us? Before Gerrit Cole’s record-setting $324 million contract (one that the Yankees tremendously overpaid in order to secure), the next biggest free agency expenditure was Masahiro Tanaka’s seven-year, $155 million deal (which coincided with the Jacoby Ellsbury, Brian McCann and Carlos Beltran spending spree).

Somehow, we’ve witnessed an era of Yankees baseball that featured bloated payrolls but without any notable superstar contracts or success on the field to show for it.

Too often it seems like the front office is keen on doing things their way. When they formulate trade packages, it’s never with the intent of “going for it all” but rather “how can we minimize risk?” Spending has now become a chore rather than an objective. One could argue there have never been this many lack of proper fits in Yankees history (Sonny Gray and Lance Lynn, just to name a couple without getting too deep into it).

But what if the Yankees had just managed to pull off timely blockbuster moves and/or high-profile trades to supplement their ailing rosters since 2013? Life would sure be a lot better.

These are the biggest free agency/trade misses in modern Yankees history.

5. Gerrit Cole Trade (With Pirates)

Gerrit Cole comes in at No. 5 because he ended up being a Yankee anyway, but if New York had gotten him for the 2018 and 2019 seasons, perhaps the Red Sox don’t go on their magical 2018 run and the Astros don’t bounce the Yankees from the 2019 ALCS. The one missing piece was an ace in the rotation, and the Bombers were so close.

The Pirates reportedly rejected a deal that included Clint Frazier at the time, which, while we laugh now, really wasn’t a bad proposal. But that’s just further proof the Yankees are blackballed on the trade market. If that’s the case, however, you might’ve wanted to make an offer Pittsburgh couldn’t refuse so they didn’t go ahead and trade Cole to one of your rivals in exchange for a four-player package of slop? The Pirates asked for Miguel Andújar alongside Frazier … and the Yankees (reportedly) said no.

In the end, Joe Musgrove, Colin Moran, Michael Feliz and Jason Martin went to the Pirates in exchange for Cole, who quickly became the second-best pitcher in baseball behind Justin Verlander (also an Astro) and they buzzsawed the Yankees in the 2019 ALCS.

How you don’t overpay for Cole here is an egregious miss. And if they were willing to, it just goes to show the Yankees are treated much differently in trade talks than most of the other teams in MLB.