5 biggest free agency and trade misses in modern Yankees history

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.

2. Shohei Ohtani (Free Agency)

OK, in the end, Shohei Ohtani didn’t want to play for the Yankees. But … why? What happened here? Throughout the entire free agent process, the Yankees were mentioned as the reported frontrunners multiple times. Who screwed this up?

Another important note here: because the Bombers missed out on Ohtani, they pivoted to Stanton, which was a monumental difference in salary (Ohtani signed for pretty much nothing since he was considered an amateur under MLB’s CBA), and ended up handicapping them financially (again, self-inflicted).

Outside of a $20 million posting fee and $2.315 million bonus, the Angels were on the hook for a league-minimum salary that’s escalated to Ohtani’s most recent two-year, $8.5 million contract … still a fraction of Stanton’s $325 million pact.

To make matters worse, the Yankees weren’t even invited to present their free agent pitch to the Japanese two-way star after opening the offseason as the frontrunner. Couldn’t even get in the room! Arguably the most prestigious worldwide sports brand couldn’t sit in a chair next to a player in Nippon Professional Baseball.

Maybe nothing happened here and Ohtani was generally disinterested playing for New York. But with how the rest of the Yankees’ free agency endeavors have gone over the past decade, we really wouldn’t put it past this front office to beef it in spectacular fashion. We’ll wait for the revelation in Ohtani’s book in 20 years.

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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The New York Yankees have imported some free agent superstars in their day! They've also brought in some absolute disasters.