How literally should I take the "Man of War" in Pirate King?
This is a challenge and the recipient must actually fight a ship of equal value in game combat, and if they win, they receive the stated reward.

From the All Hands on Deck (bottom left corner), hand management expansion:


  The Commodore's First Mate: Instead of challenging the Commodore, players may challenge the Commodore's First Mate when they land on the Commodore's spot. The First Mate's ship acts like a Man of War card. Player must fight a ship of equal in men and cannons to their own. If they win they gain 500 bronze, 1 crew &amp; 1 cannon, but if they lose normal defeat conditions apply.