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: "TWO" 
Clue: It features Jefferson on the front & the signers of the Declaration on the back

SOLUTION: two-dollar bill

PROBLEM: Category: THE HECUBA, YOU SAY 
Clue: Hecuba lays a guilt trip on this eldest son for going into his final combat

SOLUTION: hector

PROBLEM: Category: NICKNAMES 
Clue: Nickname of the Spanish-American War volunteer regiment that included Teddy Roosevelt

SOLUTION:
the rough riders