Disclaimer: The characters in this story are the property of Disney and are only used for fan related purposes.
or see spot run
Despite his diminutive size and pretty boy good looks, Spot Conlon was considered to be one of the most feared newsboys in the whole of New York. He could run faster, hit harder and shoot with dead-on accuracy better than any of the boys he lorded over in Brooklyn. He was more than feared, even—he was respected. Not a single one of his newsies would ever think of crossing him. They would rather take a short walk and a long drop into the East River than turn on their leader… it amounted to the same thing in the end, after all.
Of course, that wasn't the only reputation Spot had. Ask any of the girls—working girls, society girls, he wasn't picky—who had fallen for those steely eyes and that come hither smirk, and you would find out that not only was he the head of the Brooklyn newsies, but he was one hell of a heartbreaker, too.
That's the funny thing about the ladies he spurned. They didn't think of him the way the other boys did so, when the opportunity presented itself, two particular girls—Cinder Harrow and her unlikely girlfriend, Miss Amelia Wilkins—were not intimidated by his one reputation; they were bolstered by the other.
Some say their laughter that night echoed through even the darkest of Brooklyn's alleyways. Others say that you could hear the roar of Spot's anger on the Manhattan side of the bridge. But they were wrong. Nothing even happened that night.
The next morning, on the other hand…
Because of his diminutive size and his good old-fashioned Irish genes, Spot Conlon was considered to be a lightweight when it came to a night out with the fellas—though not a one of them would ever dare call him out on that, of course. Smart enough to know his own limits, he preferred to sit back, kick his heels up and watch his boys make complete and utter asses of themselves.
But not that night. Maybe it was the good headline that morning and a pocketful of hard-earned pennies that made him reckless, or the pretty redhead who kept smiling his way, but he matched each of his boys drink for drink. The rest of the night passed him by in a blur, a dark haze that he suspected he wouldn't remember when morning came.
He was right.
Spot woke up the next morning disoriented and in pain—though, of course, he would never admit to that, either. His head was pounding a staccato beat and his mouth tasted as if he had eaten an old sock for supper. He swallowed a few times, desperate to get the stale, dry taste out of his mouth before beginning in the unfortunate task of trying to open his eyes and start living down his monstrous hangover.
There was a good chance, he decided, that he might've overdone himself last night.
It took him a couple of tries, his eyes gummed down as they were, before he could take stock of his surroundings. Spot prided himself on knowing every inch of Brooklyn the way he knew the back of his hand, but he didn't quite recognize where he was at first—disoriented, remember? After a minute or two, he finally realized with a knowing smirk precisely what part of town he was in, including the street name he was currently lying flat on his back on: Orange Street, on the edge of Brooklyn Heights, a couple of blocks over from the lodging house he should have been sleeping in.
He had one question, though: Just what was he doing there?
Actually, make that two questions: Just how had he gotten there?
And then, finally, a third:
Why could he feel the morning breeze on his knees?
Despite his diminutive size and probably because of his big mouth, none of the fellas in Brooklyn ever felt bad about taking each and every last penny Racetrack Higgins had. Some point after discovering the hard luck gambler couldn't bluff worth a damn they decided it was better for him to lose his money to them over blowing it down at the track. They were doing him a favor, after all. At least he didn't have to hitch a trolley over to Sheepshead to go home broke.
There was something else you could say about the bummers who lived in Brooklyn. They weren't above taking every last damn cent he had, but at least they didn't kick a fella when he was down. Grinning a bit more than they should have at his expense, the boys at the Brooklyn Lodging House offered to put him up for the night, free of charge. And Race, embarrassed and broke and a bit drunker than he would have liked, had taken them up on that offer.
When he woke up, his last full cigar was gone, as well as the last of his good humor. Like a dog with his tail between his legs, he just wanted to make it back across the Brooklyn Bridge with his trousers and his shirt still on his back. The way the Brooklyners had rolled him, he considered himself lucky to be getting out with that much.
A careful sort of fellow when it came to his tobacco, Race always made sure to keep the spare ends of a near-spent cigar tucked safely inside his vest pocket, just in case. With a what-can-you-do shrug, he placed the soggy bit in between his teeth but didn't light it yet. Just the feeling of the stub clamped between his crooked teeth was good enough for now.
Lost in his thoughts, wondering how he was going to explain to Cowboy and the others how he'd managed to leave Brooklyn broker than when he arrived again, Race didn't realize that he'd turned the wrong way until it took him longer to get to the mouth of the bridge than it should've.
He found himself on the corner of Henry and Orange, shook his head once, and started down Orange. It hadn't been so long since he lived in Brooklyn that he couldn't find his way back to the bridge but something—someone, perhaps—caught his attention on the far corner.
Race rubbed his eyes, anxious teeth chomping on the stale stub of the cigar, before trying to get a better look. It was a person, he was pretty sure, and he thought it was a girl. By all rights, it ought to be a girl. There was no denying the dress, after all. But the hair was short—too short—and there was something about the way the person was groaning and rubbing their forehead that struck him as familiar.
Then again, it might've been the cane and the slingshot lying haphazardly at their feet that might've tipped him off...
"Racetrack? Race… unh... that you over there?"
Huh. So it was Spot.
Spot… dressed as a girl.
Spot… in a dress.
It took everything Race had, and then some, to keep his laughter back; as it was, he very nearly swallowed his unlit cigar. Just then he didn't know if he was the luckiest bastard alive—or the poorest schmuck who'd ever lived—to have been the one to catch Spot Conlon, hung over and in a dress.
It was mainly the part about good old Brooklyn himself being in a dress the made him want to snicker.
End Note: In the same vein of Lord of the Flies (and follow on the heels of Jack), I decided to write this three-part short story about Spot, Race and what happens after the fun night of drinking has passed. Keep it tuned for what happens next!