August 22, 1903

He hadn't meant to join the game but then again, he hardly ever intended to gamble.

Jack Kelly had many vices. Some were harmless such as smoking and reading dime novels. Others had ensured his success and survival like lying. But then there was gambling, a vice that had threatened his very existence in the world. It had been Francis Sullivan that had learned to play cards, but it had been Jack Kelly that had perfected the art of cheating. Gambling had been a byproduct of success and a healthy degree of youthful cockiness. But he wasn't young anymore, not by any standard he encountered on the streets.

He hadn't paid any attention to the three boisterous young gentlemen that entered the Little Shamrock just after nightfall. Busy finishing a letter to Audrey by taking advantage of the bright lights of the bar and the available ale, Jack scribbled away in peace among the chaos. There had been a new gentleman's name in Audrey's recent letter and Jack boiled over to demanded to know more of this new character in her life. He had received news from Skittery and Racetrack skirting around the gossip of Audrey being courted, again by others that were not Jacob Henry Canterbury. The whole of Manhattan had been so sure that Jacob would propose that it had almost insulted Jack when he apparently hadn't. Young Canterbury had up and sailed across the Atlantic Ocean with not so much as a scandalous broken heart or more than a passing lament to a lonely summer from Audrey, though Jack suspected there was more to that story. The curiosity was eating Jack alive, but he knew better than to ask, understood the answer might drive him mad. But if others were courting Miss Kai, the notion of her being coupled with Canterbury must be out of style at least for the summer season. Jack didn't know if he was relieved or terrified.

The game had started while Jack contemplated his feelings and tried to shake the lonely ache he wouldn't identify. A brash bang of glasses on one of the sturdy tables near the entrance, shoving of chairs and dropping of handfuls of coin. Jack had been caught up with a particularly detailed description of a sunset, trying to paint the colors into words for Audrey, and hadn't even glanced over.

There had been three hands before Jack felt his ink had dried enough to let him fold up the letter, ready to be stuff into a stiff envelope inside his coat pocket before he noticed them. Finely dressed in evening suits and polished shoes, the trio of young gentlemen had wandered a few too many blocks from the club. They were enjoying themselves, even losing coins as they were clearly doing. The tallest sitting to the left was clumsily untying his necktie as he waved a lanky arm about signaling for more ales. The one to the right was lighting the fattest cigar Jack had ever seen and impatiently tapping his cards onto the table. But it was the one in the middle that caught Jack's attention, a bit younger than the one to the right and with flushed cheeks and glassy eyes it would be easy to peg the boy almost man as drunk. But it was a tilt of the chin, a flick of the wrist flashing his cards – another losing hand – a desperation that was easy to see as a losing streak fueled by some unspoken rage that was interesting. The boy's clenched fist twinkled in the bar lights, and Jack caught sight of a woman's ring on the young man's pinkie finger.

"That lad is a fool, sporting his broken heart out in the open for the scoundrels in here to take advantage of him." Miss Julia grumbled from behind the bar.

Jack suddenly recognized the heartbreak, the look of despair that had grown so familiar in Conlon was matched tenfold by this boy.

"Worried for the mucky-muck?" Jack smiled at her.

"Money brings trouble." Miss Julia frowned up at Jack as she poured more ales.

"He seems to be on a losing streak, maybe he's not enough of a fool to play once he's lost all the coin in his pocket." Jack shrugged as he settled his bill.

"Mark my words, he'll see that ring lost in a game of poker over letting it weigh down his pockets." Julia shook her head, wiping an arm across her sweating forehead.

The ring. It was a gold band with at least three red stones and two diamonds set into a delicate and intricately floral design. An engagement ring like that was worth well over anything Jack Kelly could ever imagine, likely more than a month's wages.

He hadn't meant to play. Later, he wouldn't remember making the decision to walk over to the table. He'd be unable to recall pulling out one of only three crisp dollar bills he had to his name and setting it down with the other bets. But Jack Kelly would never forget the excited glint of a challenge the boy with the ring flashed his way.

There was a haze in the pub, a heaviness that shaped each breath with a curve and lift of smoke from an endless supply of cigarettes. The way his eyes burned, and his limbs ached reminded Jack just how long it had been since he'd been dealt into the game. A dull chime sounded from somewhere behind him, the sound of midnight falling.

Spot Conlon growled at the clock, or maybe at the time, even the man himself might not know where his ire was directed. Spot had entered the Shamrock an hour before, impatient with worry for a missing Jack Kelly only to discover his friend gambling.

Conlon had a scowl on his face and his fingers were curled into fists in a way that was familiar like a dream but not quite memory anymore. Conlon sat ramrod straight, patient, and silent just an arm's length behind Jack. He hadn't even said more than three words since entering the pub, but Jack could feel the brimming anger in the familiar personality of impatience. If Jack hadn't been winning, an honest hot streak, the once leader of Brooklyn would have put a stop to the game. A stop, Jack had no doubt, that would have ended with a fist to his face. Unconsciously, Jack rubbed at his chin, and he heard another low growl confirming his suspicions. When they had been younger, it hadn't taken long for Jack's luck to turn sour and his vice to turn violent. It had been Conlon who had helped beat him out of the habit and diminish Jack's itch to be a kind of reckless that brought endless pleasure from possibilities.

But Jack had been winning. Quarters stacked as high as his thumb with crumpled-up dollar bills, and two cigars made up his winnings. Hours of poker had made Jack Kelly more than a week's worth of wages and he knew he should retreat to bed before he lost it all as easily as he had won it.

"Call." Jack pushed the crumpled-up dollars back into the center. Exactly 6 dollars, nearly a fortune by newsboy standards but it wouldn't hurt to lose the money he hadn't had two hours before. Money that had once belonged to his opponent anyway.

"Christ." The man across the way grumbled, patting at his coat pockets.

"Billy, maybe we should bid the night farewell." The rosy-cheeked fellow that had been smoking cigars most of the night and that Jack was sure wouldn't be able to stand without swaying considerably, remarked.

"No one asked you, Pete," Billy growled, now pawing at his trouser pockets.

Billy wasn't much older than Jack himself, clean-shaven the man looked like he might even be younger, and it was an odd sensation not to know or even to care. William Hamilton was out to forget a broken heart and Jack just happened to be aiding in his efforts.

"It's your fault we're here at all Peter." The last man, Edward sighed as he brought back a couple of mugs of ale from the bar. Edward had burned through his earlier inebriation by pacing for the last hour, occasionally carrying ales from the bar to the table. Edward was the only mucky-muck that hadn't played every dollar in his coat and had refrained from continuing to drink or smoke. He was the sensible one and if Jack had to wager, which with his present luck was inevitable, Edward was William's older brother.

"Give me more to gamble away, Edward." Billy smiled up at his brother. All of William's pockets were turned out, and the man looked like a helpless schoolboy with his hair out of place, flushed cheeks, and swimming eyes. Edward had already had to confiscate a family pocket watch from the boy before it had been placed against the bets earlier.

"Not on your life Billy Boy. You've lost enough for the evening." Edward stepped back, out of reach as his brother's arm swung out.

Spot leaned forward and rapped his knuckles on the table with considerable force. The three wealthy gentlemen were startled enough to focus on the table.

"Miss Julia would like to get to her bed at some point this evening gentlemen." Spot pointed out impatient.

The Little Shamrock was quiet and dimmer than it usually was, and Miss Julia sat quietly doing her mending under one of the lamps. She was clearly waiting for the game to cease before firmly pushing all the men out the door and closing completely.

Billy stared down at the table again, his eyes counting the items Jack had pushed forward.

"Do you think you're lucky?" Billy frowned at the cards in Jack's hand.

"Fold, Kelly," Spot whispered as he yawned. Jack knew Spot wanted to get to bed just as well as he knew Conlon would never leave Kelly gambling in the pub alone.

Billy started fidgeting with the ring on his pinkie, twisting it and turning it anxiously. Jack tried not to fix his gaze on the bright little band.

"Luck's a curious thing." Jack pressed his tongue against his front teeth and inhaled slowly. The noise filling the space between the men.

"Have you ever loved anyone, Kelly?' Billy leaned forward, letting his cards sit face down between his elbows. The boy used his thumb to push the ring up his pinkie, hitting his knuckle before letting it slip back down again.

"Yes." Jack nodded immediately.

William Hamilton was heartbroken. Over the hours of card play, Jack had learned that a young lady known to him only as Margie had refused the boy's marriage proposal. The proposal had been impulsive and ill-timed according to Edward. While Peter believed the young lady in question had been using Billy to make another suitor jealous and never intended to accept. It had been a surprisingly loud argument.

"Did she love you back?" Billy asked still pushing the ring up and letting it fall. Jack had been watching the same movement all night.

"I don't know," Jack whispered before he could think not to. Billy smiled at the admission while Spot frowned but settled back into his chair, arms crossed.

Billy swung his ale up and gulped it down. He ran his shirt sleeve across his jaw, catching the dribble at the corners of his mouth as he grinned. He flicked his thumb, pushing the ring up and over his knuckle and clattering onto the table. Edward huffed out a laugh as he shook his head at his younger brother's antics.

"I'd find out if I was you…" Billy's lip curled over his teeth in a real smile as he flipped his cards over.

Jack didn't need to look at his own cards to know he'd won. The six dollars, the cigars, and the brilliant little ring. An engagement ring fit for a society lady. He set his cards down and pushed them forward to allow the three gentlemen to study them before he moved towards his winnings.

"…Before I offered her that there pretty little thing. May it bring you more luck than it did me, Mr. Kelly." William Hamilton pushed himself up and away from the table. He grabbed hold of Peter with surprising steadiness and pulled his friend to stand. Edward was quietly murmuring his thanks to Miss Julia as he settled their tab.

William stepped out into the night without a look back or a farewell. Jack blinked down at the pile of winnings, letting his hand wander to the ring, instantly pinching it between two fingers. It felt delicate and strong, warm to the touch.

"Thank You," Edward said quietly and Jack was startled to realize the man was starring right at him. Jack nodded only once before Edward disappeared into the street after his brother and Peter.

"Never seen anyone thank you for cheating before." Spot whistled as he swiped a cigar from the table. Jack thought fleetingly about denying the claim but shrugged it away as he played with the little ring on his own pinkie.

"He was going to play until he lost the ring," Jack explained. Spot hummed in agreement.

"I ever catch you gambling again, I'll give you matching shiners on that mug of yours before I break three of your fingers." Spot threatened as he cracked his knuckles and stretched to stand.

Jack ignored the threat as he scooped up his winnings, shoving coins and paper money into different pockets. Spot jabbed his elbow into the side of Jack's stomach, once.

"I heard you, Conlon." Jack snapped as he slipped the ring onto his own pinkie.