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Have You Always Been Their Leader?

Summary:

5 newsies Jack recruited + the 1 who recruited him.

Notes:

Content warnings are listed in the summary of each chapter.

These aren't necessarily my personal headcanons, I just thought it would be a fun challenge to create my own backstories for some of the characters. (Although, I did borrow a few details from canon, fandom lore, and actors' interpretations.)

Have fun and enjoy!

(See the end of the work for more notes.)

Chapter 1: 1

Summary:

Content warnings: smoking, gambling, brief mentioning of death, referenced child abuse

Chapter Text

At age thirteen, Jack Kelly dreamed of a big life in a small town out west. Instead, he found himself the leader and top seller of the Newsboys' Lodging House of Manhattan, New York. One of the most renowned and respected amongst his peers.

He and his fellow newsies were all set to hit the streets again one morning when the front door swung open and an unfamiliar face entered the lodge. Jack eyed the new arrival suspiciously: a young boy, only disheveled enough to get across that he'd tried hard not to be disheveled, who had false confidence written all over him. Intrigued, Jack approached him.

"Ain't seen you before," he interrogated. "What brings ya here?"

The boy stepped forward, clearing his throat. "I'se lookin' for a job," he said, the words clearly rehearsed. "Here's my resumé." He extended his hand, revealing a scrappy piece of paper.

"Resumé?" Jack laughed. The other boys snickered behind him.

The new kid blushed and turned to leave when Jack stopped him.

"Ey, wait!" He snatched the paper from his hand. "Let's see what 'cha got."

Jack examined the handwritten document carefully while the rest of the newsies looked on in silence and the newcomer stared down at his shoes. "Antonio?"

The blond boy nodded.

He was surprised to learn that the kid was just a year younger than himself, as he originally thought him to be much younger. Jack continued reading, his eyebrow raising in confusion. "You live at the Sheepshead Bay track?"

"Well, no," Antonio explained, "I lives nowhere. But if ya ever needs to find me, I spend a lotta time there."

Jack's eyes moved to another section of the page where Antonio had listed his skills. "Can you'se really guess who's gonna win the horse races?" he asked, skeptical, but impressed.

Antonio nodded again, regaining some confidence. "Yeah."

A symphony of "ooh's" and "ahh's" rippled throughout the group.

"Sometimes," Antonio added in a slightly smaller voice, prompting a collective chuckle from the newsboys.

Jack grinned. "I like you, Antonio."

"Thanks," the boy smiled back. "They call me Tony."

"Well, Tony, I'll spot your first twenty papes and then you'se can pay me back at the end of the day. Deal?" Jack spit into the palm of his right hand and extended it forward.

"Deal!" Tony mirrored his actions and the two boys secured the agreement as the surrounding newsboys cheered.

"Stick with me and I'll show ya how it's done."

Turns out, Tony barely even needed Jack's help. The kid was a natural. He knew exactly what to say to each passerby to earn their business, being able to switch back-and-forth from "sad, helpless child" to "charming ladies man" at the drop of a hat. And if he couldn't get their pennies, he would swiftly snatch himself a cigar from their pockets and call it a square deal. Suffice to say, Jack was impressed, especially after how shy he'd seemed at the lodge earlier that morning. In one day, Tony made more than enough money to pay him back and buy his own papers the next day.

The two became quick friends. When they weren't selling newspapers, they could often be found chasing each other through the park or sneaking in to watch the horses race. Tony was right, he did spend a lot of time at Sheepshead, earning himself the nickname "Racetrack" which was later shortened to "Race" or "Racer." 

They had a lot of fun together and formed a strong emotional bond, as well. At the end of most days, when the rest of the newsies went to sleep, Jack and Racetrack would sneak onto the roof of the lodging house to chat and smoke cigars. Well, Race did most of the smoking. Jack never really saw the appeal. He honestly thought they were pretty gross, but Race said that the cigars helped him relax ever since his mother died, so Jack never said anything about them. As he got to know Race more, Jack learned that the two of them were a lot alike. Both of their mothers were gone, but his father wasn't locked up like Jack's was. Though, from the few stories that Race told about him, it sure sounded like he oughta been. All the kids at the lodge had rough upbringings, too, but it was nice for Jack to find someone who he could relate to so specifically. Someone who understood him.

Over time, as he got more comfortable around the other newsies, Race became sort of the "class clown" of the group. His wit was impeccable and he knew just how to use it to his advantage, whether it be to win an argument or to offer some comic relief if the fellas were having a bad day.

Jack watched with a sense of pride as Race's confidence continued to grow, taking it as confirmation that he must be doing a pretty good job as a leader himself.