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.