TASK DEFINITION: You will be given a trivia clue, and the category it belongs to. You should answer with the best answer that belongs in the category and is described by the clue. For simplicity, answers should be in all lower cased letters.
PROBLEM: Category: THE CHIEFS 
Clue: He wrote 5 of the 85 "Federalist" essays

SOLUTION: john jay

PROBLEM: Category: LESSER-KNOWN PROVERBS 
Clue: It specifically "tries truth" as well as generally "tries all things"

SOLUTION: time

PROBLEM: Category: FLAGS 
Clue: Christopher Columbus' flag bore a cross with their initials on either side

SOLUTION:
ferdinand & isabella