Yankees Brian Cashman and the judgment of the present hour
The team will continue to get younger and better while maintaining the vast majority of a probable playoff nucleus. Only Jaime Garcia, Todd Frazier, Michael Pineda, CC Sabathia, Matt Holliday, and Masahiro Tanaka are possible significant losses. It is more likely that Tanaka returns, and it’s possible that either CC or Garcia also return, along with Holliday.
The Yankees will also likely shed both Chase Headley and Jacoby Ellsbury, as well as trade either Didi Gregorius or Starlin Castro at some point during the next 12 months. Starlin has one more year under team control than Didi, making him more likely to be retained.
Replacing some of those players will be Miguel Andujar and all-world Gleyber Torres; Andy might still take over the hot corner this year. The Didi/Castro trade will undoubtedly bring back a significant, young starting pitcher, adding to a strength.
And Cashman has been slashing the salaries with this exact time frame in mind. With at least $40 million to spend this off-season, He will be able to afford Yu Darvish, the best free agent pitcher this year and a true ace. I am sure he has already set up a meeting with Darvish and Hideki Matsui, along with his good friend Derek Jeter.
They can explain what it’s like to win a World Series as a Yankees player, both for Yu Darvish the baseball player, and Yu Darvish the international brand.