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who wins

Does Johnny Sorrow have any psychic resistance?

Depends on which version of Pirate.

Post crisis (pre Flashpoint) The medusa mask could bring Pirate back to life which makes Sorrow's power to kill by seeing his face invalid. Pirate's ability to control emotions is uber enough to give him the win for a majority.

Nu52 the mask allows him TP instead of emotional control on a planetary level. It doesn't bring him back so all Sorrow has to do is show him his face for the win. Depends on if Pirate can TP detect and know that inntime