The four times Jack couldn't cry and the one time he did.

Jack Kelly was by no means heartless. Any newise could tell you that. Sure he was rough on the outside but he still tucked the littles into bed at night. He still made sure to keep extra money to stock up on medicine. He still went out and sold with a cocky smile on his face and charm in his words every day. He still roughhoused with the boys even though he was 17 and he should be acting like an adult. He still scolded Race for smoking inside the lodging house because "'it's bad fer' da lungs."So no, Jack Kelly was not a heartless boy. He just never cries. He has no problem being open about his emotions but no one has ever seen Jack Kelly cry. Until one day, he did.