5 biggest free agency and trade misses in modern Yankees history

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.