Disclaimer: This is a non-commercial work of fanfiction. Anything recognizable from Newsies belongs to Disney and not to me.

Chapter 8: Making a Judgment

A/N: The events of this chapter are taking place concurrent with the events of the previous one.


The sketch, Katherine had to admit, was a rather good likeness. That impossible boy - that scruffy, ragamuffin artist - had captured the curve of her cheek, the tilt of her nose, even her slightly troubled gaze perfectly (he should have, she thought irritably, seeing that he was the cause of it).

Still, she wasn't sure what to do with the drawing that he'd left behind. It felt overly-sentimental to keep it, but there was so much skill apparent in even the hastily-executed strokes that it seemed almost offensive to throw it away (it was, after all, a beautiful sketch and a rather good likeness - not that she was at all being vain about it).

In the end, she settled for tucking it into her notepad under her scribblings, which had started out orderly but had become regretfully more chaotic and difficult to read once the boy had barged into her private box at the theater where she'd been observing the show for the review that she'd been tasked with writing for The Sun. Katherine had been instantly annoyed by the interruption, not at all interested in the boy's flirtatious attention; she received enough of that at the office and certainly didn't need more of it in the field.

But she had to admit that he'd been quick-witted, and that their banter had been...an unexpected and interesting diversion. He'd asked curiously about her work, hadn't balked when she'd insulted him, and had declared her a "smart girl" (whether it was in reference to her profession or to her cutting retort was irrelevant; "smart" was not something that she was used to hearing from an admirer in reference to herself, though she certainly thought it quite a fitting descriptor).

It didn't hurt that he'd noticed her beauty as well. Katherine had been called all manner of lovely things on numerous occasions, both by those with sincere intentions and those without, so the boy's complimentary words hadn't made much of an impression on her. His drawing, however, was another story. In a few lines of charcoal pencil on paper, he'd shown her what he saw when he'd looked at her...and it had been quite breathtaking.

So when he'd cockily taken his leave with a smirk and a flourish, tossing the sketch down onto the chair beside Katherine, she'd almost been a little sad to see him go, not simply because she'd enjoyed his attention, but because there was something about him that intrigued her.

He was obviously not well-off - both his attire and his manner of speaking had made that clear - yet his artistry exuded a fascinating tension between the refined and the raw. She wasn't sure where the former came from, but it was unmistakably there. (If Wilde was correct, then here, perhaps, was a contradiction).

Was the boy a student, selling papers to work his way through art school? Or was he merely a newsie with a hidden talent that he only indulged in during the short snatches of time between his never-ending work of hawking headlines? Did he have parents who encouraged his skill, or was he an orphan, making his way on his own? Was he even aware of the gift that he possessed and of where it could take him, or was he ignorant of the fact that what he had was something extraordinary? His profession was a humble one to say the least, but his personality was somehow larger than life - did he know that he possessed some kind of unmistakable magnetism that even his worn-out clothes and dirty face couldn't hide?

The questions fascinated Katherine, tickling and taunting her by turns until she finally gave an exasperated sigh of resignation, admitting to herself that her curiosity had been piqued.

This boy was a story she wanted to follow. And he'd left behind sufficient clues for that to be easy enough.

His name was Jack Kelly. He worked for The World.

She'd tracked people down on less information than that, and he'd be no different.

Having settled this in her mind, Katherine tucked her notebook under her arm, careful not to wrinkle the sketch, then quickly left the now-empty theater, heading for her office at The Sun.

She had an article to write, and once that was done, she had a certain newsboy to find.

(She most certainly wasn't intrigued by his handsome face or boyish charm. She was only a reporter sniffing out a story).


"Lights out in five!" Jack barked over the commotion of the lodging house.

"Come on, fellas - you heard Jack! Get movin'," Race chided, swatting Albert with a towel as the ginger-haired newsie thumbed his nose at him.

It was past midnight, and the newsies should have gone to bed hours ago, but Race and Mush had been embroiled in a particularly heated card game, and Jack and the other boys had become so engrossed in it that they'd lost track of the time. There would certainly be a few sleepy newsies at the circulation gate come daybreak, and Jack made a mental note to make his wakeup call a bit earlier, knowing that some of the boys would have a particularly difficult time rousing themselves after a short night's sleep.

Once all of the newsies had settled in for the night and the last talker (Albert again) had been shushed, Jack took one final look around the room, giving the still-standing Race a quick nod before extinguishing the lights. He turned around and started down the stairs to the ground floor, not even bothering to listen for the gambler's light footsteps as he left the bunk room and followed.

They didn't speak until they'd stepped outside of the lodging house and into the evening air, which by this time had turned pleasantly cool.

"So, what'd ya think of our newest additions?" Jack asked Race as the other boy leaned casually back against the wall and struck a match.

"The kid's a quick study," Race replied, lighting his cigar. "From what I've seen, he's gonna be up to speed in no time." He paused to stamp out the match, then added, "Not so sure about his brother, though."

Jack settled himself onto a barrel nearby. "You think he ain't got what it takes?"

Race's answer surprised him. "I think that's gonna depend on you, Jacky."

"What do you mean?"

"I mean if you try and make Davey sell papes the way the rest of us do, he ain't ever gonna be any good at it," Race elaborated.

"That's for sure," Jack let out a little snort, remembering Davey's scruples over improving the truth.

"But," Race continued, gesturing with his cigar, "I think if you let him figure out his own way of sellin'...he might find an angle that the rest of us ain't got. Most folks get suckered into a sale when we's makin' up some kind of crazy story, but then there's those types who actually want the real news without all of the exaggeratin' we's always doin.' Those folks is the kind that'll buy a pape from a kid like Davey." Race paused, then added, "He's got the look, ya know?"

Jack agreed. While he'd immediately pegged Les as the more marketable of the two brothers (and certainly, the kid was a charmer), he had noticed from the start that there was something remarkable about Davey, though he hadn't been able to pin down exactly what it was.

He'd actually let Davey sell on his own for most of the day on purpose, wanting to see what he was capable of accomplishing when left to his own devices. And, to his surprise, Davey had somehow managed to sell almost all of his papers by evening. From what Jack had seen, his selling technique was awkward and forced to say the least, but people had still purchased from him, so maybe Race was on to something. The gambler was unpredictable, sarcastic, and occasionally moody, but his rare flashes of insight were rarely wrong.

They were a good team, Jack and Race, when it came to assessing people. Jack drew his conclusions intuitively, preferring to trust his gut. He only needed a few interactions with a person to get a sense of them, and his natural charisma drew people out before they even knew what they were divulging.

Race, on the other hand, looked for tells. He was always watching people, and the hours he'd spent reading faces at the card table meant that he'd become an expert at catching the quick and fleeting things that could often tell you more about a person's motives than their words. Very little escaped Race's keen eye, and Jack had relied on it time and time again to catch the things that he himself would otherwise miss.

They had made it a practice to compare notes any time a new newsie joined their ranks, careful of whom they allowed into their inner circle. If their evaluations matched and were positive, the newcomer was promptly welcomed into the brotherhood. If one or the other had misgivings, both would keep a watchful eye on the newsie in question until further assessment could be made. On the rare occasion that they came up with matching concerns or suspicions of ill-intent, measures were taken to ensure that the outsider was kept from infiltrating the ranks of the lodging house. It was, perhaps, a bit of a drastic response, but they'd learned the hard way that you couldn't trust everyone, and that a careless oversight could, in the worst of cases, prove disastrous.

Jack shook his head, pushing away memories that he wished he could forget.

"So, sellin' potential aside, you think they's trustworthy?" Race asked, bringing him back to the present.

Jack laughed, thankful to have been pulled away from his brooding thoughts.

"Trustworthy?" he echoed. "When one of 'em's nine years old and the other can't lie to save his life?"

"Careful, Jacky," Race warned with a grin. "Ain't ever a good idea to underestimate a nine-year-old."

"Yeah, yeah," Jack chuckled, swatting the other newsie with his cap.

"So, we's in agreement, then?" Race asked. "They's in?" Jack nodded, readjusting his cap on his head. There hadn't been much to deliberate on this time, but he felt better having come to the same conclusion as Race.

"Good." Race snuffed out his cigar and straightened up. He glanced at the moon, as though pondering the lateness of the hour and debating about something, then, seeming to make up his mind, took two steps towards the lodging house door. "You sleepin' on the roof tonight, Jacky?" he called over his shoulder.

"Yeah," Jack answered. "Night, Racetrack."

He walked around to the back of the lodging house, then pulled himself up onto the fire escape that led to the rooftop.

Crutchie was already there, stretched out in his usual spot, and Jack quietly stepped off of the fire escape, cringing as it creaked a little. He took several tentative steps towards the corner of the rooftop where he typically slept, trying to be as silent as possible as he passed the other newsie's sleeping form.

"What'd Race think?" Crutchie asked, his voice drowsy but curious.

Jack turned, guilty for having woken up his friend.

"Gave his approval," he answered quickly. "Go back to sleep, Crutchie."

The other boy nodded in satisfaction. "I got a good feelin' about them, Jack," he murmured. "Goodnight."

"Night, Crutchie."

Jack walked over to his corner of the rooftop, pausing for a moment to take in the sleeping city before removing his cap and outer shirt and setting them in their usual spots. Then he laid down, hands behind his head, and stared up at the night sky, watching the scattering of stars that gleamed and glittered high above him.

It had been an eventful day.

Jack was thankful for many things: thankful that it had been a productive day of selling, thankful that the weather had been mild, thankful that Snyder had been easy enough to outrun (this time) and that Ms. Medda had been at the theater, thankful that Race had won his card game and had been in a talkative mood, thankful that they had been in agreement about Davey and Les, thankful that the newsies in question seemed to be honest enough (though Les was shaping up to be a first-rate liar when it came to selling headlines)...

...and thankful that he'd gotten a second chance to run into that bewitching, feisty reporter.

Jack rolled over on his side, his hand reaching for the little sketchpad that he always had on his person and at night left beside his makeshift bed (which was really just a few tattered blankets thrown together). Flipping to the most recent sketch, he examined it with a scrutinizing eye.

The drawing he'd done at the theater had been much better, but there was something about this very first sketch that was special. Maybe it was because he'd only seen her for a few fleeting seconds at that point before she'd breezed off, yet somehow he'd still managed to capture a tiny bit of her in the hasty portrait he'd sketched later that day when the papes hadn't been moving and he'd had some time to himself.

With a small smile, Jack tucked the sketchpad carefully away, then turned over on his back again, staring at the stars.

He couldn't get her out of his mind.

Who was she? He'd gotten a little closer to figuring that out - he now knew that she was a working girl (and liked her the better for it), and that she wrote for The New York Sun. He'd tried again to flirt with her, thinking that perhaps in the absence of the gentleman friend she'd been with earlier she'd be a bit more open, but she'd snubbed Jack as mercilessly and persistently as before, and oddly enough, he liked her the better for that as well. She was beautiful, smart, witty, self-assured...and not the least bit interested in him.

It was a heady combination.

Jack had known other girls before, but his attention had never been captured like this. He wasn't sure exactly what the difference was (but honestly, did it even matter?); he only felt that she was something special. It couldn't be explained.

One thing he was sure of: he would see her again. If fate could bring them both to Ms. Medda's theater for a second meeting under the most unusual circumstances, it would only be a matter of time before their paths crossed again. And when they did, Jack would certainly be ready.

Feeling more hopeful and content than he'd felt in a while, Jack closed his eyes, letting the weariness of a long day and the lateness of the hour settle upon him like a blanket.

Soon his thoughts were drifting off towards sleep, bound for plains of rolling green grass and a clay-walled city that rested under a blindingly brilliant blue sky.


A/N: Am I the only person that thought it was strange that in the musical, Jack waited until Davey was selling his second-to-last paper to correct his selling technique ("Sing them to sleep, why don'tcha?") if they were supposedly selling together all day? Anyway, my theory for this is that Jack actually let Davey sell on his own for the reasons mentioned in this chapter, and only bothered to correct him when he returned much later to see how the new kid was getting along.

In Katherine's section, the mention of (Oscar) Wilde is in reference to an essay he wrote in 1889 called "The Decay of Lying," which expressed Wilde's opinion that "Life imitates Art far more than Art imitates Life." Katherine draws a somewhat oblique and indirect connection to this thought as she's considering Jack's artistic abilities, noting that his artistic style is a reflection of his personality (art imitating life as opposed to the opposite). Sorry. This is what you get when you have a former AP Art History/AP English student as your author. :)

Anyway, I'd love to hear your thoughts on this chapter if you're willing to share! Your feedback truly does keep me going. Thanks for reading, and I promise we'll get to the strike soon!