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.

4. Zack Wheeler (Trade With Mets and Then Free Agency)

Once Cole was no longer attainable as a member of the Astros, the Yankees once again attempted to bolster their rotation, this time ahead of the 2019 trade deadline. The Mets were floundering and Zack Wheeler was about to hit free agency. With general manager Brodie Van Wagenen calling the shots in Queens, really anything was possible.

So the story goes: the Yankees and Mets had a deal in place for Wheeler. We were about to see a crosstown trade for the first time in forever. But then one player’s medicals saw the transaction fall through and that was it. Wheeler remained a Met and then left that offseason, which we’ll get to in a second.

But, again, something goes off course and the Yankees seemingly refuse to adjust. Medicals fell through? Team wants another player? Why are we sitting here with our arms crossed and saying “no”? Amend the deal! Overpay a little! We’re not saying give away the team’s top three prospects, but you can’t tell us appropriate amends couldn’t have been made.

Then, that offseason, Wheeler signed with the Philadelphia Phillies on one of the most cost-effective deals we might see in a long time: five years and $118 million for a guy who’s now morphed into an NL Cy Young candidate.

If the Yankees liked Wheeler so much that they were willing to surrender assets for just two months of him (with hopes he’d help lead them through the postseason) then why wouldn’t they tack on another $118 million that offseason after they paid Cole? That’s a small expenditure for this front office and they would’ve set their rotation up for at least the next four years.

Instead, they whiffed on the trade market and in free agency within months of each other.

3. Bryce Harper (Free Agency)

There’s not a single Yankees fan out there who had doubts about Bryce Harper coming to the Bronx back when the slugger was a Washington National. This was the quintessential Yankee once upon a time. The most hyped prospect of our time. And he delivered. Rookie of the Year. MVP.

Only problem? The Yankees had Aaron Judge in right field, so when the 2018 offseason arrived, there seemingly wasn’t a fit. But there’s always a fit for a player of Harper’s caliber, and his 13-year, $330 million contract actually ended up not being as crippling as many expected. Harper will make only $22 million per season in his age-36-38 campaigns. Not bad.

But because of the Giancarlo Stanton acquisition a year prior, there was no way the Yankees were putting another $300 million contract on the books while also creating a logjam in the outfield. Though Stanton’s come around since the 2020 playoffs, the Yankees acquiring him was a bit of a mystery at the time. He had a well-documented injury history and was slated for the DH role sooner rather than later. Instead of waiting a year for Harper, they traded for Stanton, and then used Stanton’s contract as an excuse not to spend big on the next star-studded free agent class (not even Patrick Corbin?!).

In a perfect world, you simply sign Harper and make it work. Say goodbye to Brett Gardner. Trade Aaron Hicks. Whatever you have to do, you do it. Harper is on his way to becoming a future Hall of Famer and the Yankees surely could’ve figured out a way to make him a roving outfield option if they were serious about planting Judge in right field ( … even though they weren’t because he played center field in 2021).

Historic miss here.

1. Max Scherzer (Free Agency)

Back in 2015, the Washington Nationals signed Max Scherzer to a seven-year, $210 million contract during an offseason in which the Yankees badly needed pitching. They had signed Tanaka the year prior, but a partial UCL tear created a ton of uncertainty.

Scherzer was hitting his career stride, too. His previous two seasons before the mega deal saw him win a Cy Young award, lead the AL in wins twice, lead the AL in WHIP, and record at least 240 strikeouts each year. This was the guy. And for $30 million a year? At the time, sure, a bit pricey, but five years down the road? Likely a bargain.

In the end, Scherzer solidified his Hall of Fame case during his tenure with the Nats while the Yankees underachieved because … they had no pitching! They attempted some patchwork moves with Michael Pineda, Nathan Eovaldi, Sonny Gray, Lance Lynn, JA Happ and James Paxton … none of which really worked to varying degrees.

Again, why try and get fancy when you have the resources to spend the money necessary to acquire arguably the best pitcher of this generation? If the Yankees have Scherzer, he pitches the 2015 Wild Card Game and they probably don’t get embarrassed by Houston. Perhaps they make the playoffs in 2016. They likely win the 2017 ALCS. The Red Sox definitely don’t steamroll them in 2018. And we can account for seven games in the 2019 ALCS, at the very least.

We’ll never stop complaining about this failure.

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