Entering the 2021 trade deadline, the Yankees are at a crossroads. At three games over .500 with a negative run differential, especially coming off of a brutal sweep at the hands of the Red Sox, the team looks as far from a playoff team as it has all year. Certainly, they’ll want to keep their chances of contending in 2022 alive, considering it’ll be Aaron Judge’s final year of arbitration-eligible pay before reaching free agency. Also, they’ve already got a third of a billion dollars committed to the triumvirate of thirty-plus-year-olds in Gerrit Cole, Giancarlo Stanton, and DJ LeMahieu.