This was inspired by a conversation between me and my friend. The only differences are that the money in question was a hundred dollars, and nobody actually jumped in the water.
A Dillar, a Dollar
"Hey Spot," Whistler said, skipping a stone over the surface of the water. It skipped twice and then sank. "'F I gave a dollar for jumpin' in the Hudson, would ya do it?"
It was late October. Spot looked at his second-in-command as if the older boy had grown an extra head. "With clothes on or naked?" was Spot's reply.
"Either one," Whistler answered.
"Ya got a dollar on ya?"
Whistler grinned his famous grin. "Maay-be—"
Spot searched Whistler's face for any sign that of the truth. He mentally cursed the redhead's famous poker face. "I'm not doin' it unless you show me the dollar," he said.
Whistler shrugged, then pulled a quarter, three dimes, seven nickels, and ten pennies out of his pocket. Spot watched as he carefully counted the change, setting each coin on the wooden planks of the pier between the two boys.
"—Fifty-five, sixty, eighty, ninety, a hundred," said Whistler, adding it up in his head. "There's yer dollar, Spot."
Spot's jaw dropped nearly to the floor. "You serious?" he asked. Whistler merely grinned. The temptation to punch that smug look off his face was growing by the second. "Sure, why not." The King of Brooklyn stood up and proceeded to remove his boots, setting them aside carefully along with his slingshot, cane, and gray cabbie hat. He took a deep breath and jumped over the edge of the pier into the icy cold river.
The freezing water took his breath away in an instant. Spot came up to the surface shivering and spluttering, thinking only of the dollar Whistler had promised him. Thrashing wildly, he made his way over to the ladder and hauled himself back onto the pier, soaked to the skin.
Whistler took one look at his superior and began laughing hysterically as Spot shivered and tried to wring the worst of the water out of his dark blond hair.
"Whatchoo laughin' at?" Spot demanded, pulling his boots back on.
"You," Whistler replied.
"Yah, yah, gimme me dollar before I soak ya." Whistler handed over the coins. They quickly disappeared into Spot's pocket. Whistler started laughing again.
"What is it now?" Spot asked.
"Nuthin'," Whistler said. "Jus' that you owe Racetrack a dollar, and he owes me one."
"What the hell's that supposed to mean?"
"I bet him that you would jump in the Hudson for a dollar, if he'd provide the dollar. 'F I lost the bet I'd have to give back the dollar, plus interest, an' if he lost the bet, you'd pay him back just the dollar," Whistler explained. "So since I won the bet, you have to give that dollar back to Racetrack." Spot's face went from light tan to oatmeal coloured, then to bright flaming red as he shut his eyes and tried to stop shivering long enough to collect his thoughts.
"Whistler," he said. "So help me, if you don't start runnin' right now, I'm gonna beat you to a bloody pulp and chuck you in the river."
Whistler jumped to his feet and ran, Spot following close behind. They were at the bridge when Whistler came to an abrupt stop, right before losing his balance and crashing headlong into Racetrack, who was coming over from Manhattan to collect his money.
"Whatcha runnin' for, Whistler?" he asked.
Whistler glanced behind him, where Spot was running, still soaking wet. "Well, the King of Brooklyn took offense to being bet on like a horse, and he's plannin' on beatin' me up and chuckin' me in the river in revenge," Whistler said. "Don't suppose you could help me get him calmed down."
"Hell, Brooklyn's in a bad mood? I'm stayin' clear," said Racetrack. "Make sure you get me my money back." With that, he took off, holding his cigar so it wouldn't fall out of his mouth as he ran.
By now Spot had caught up with Whistler. He threw a punch at the older boy, who dodged it and brought his left fist up into Spot's gut. Spot doubled over, recovered, and pulled Whistler's ankles out from under him.
"You always like to keep things even, right Wiss?" Spot said, grinning as he pinned Whistler to the ground. "Well, so do I." Spot's right fist connected with Whistler's nose. "That's for makin' the bet." Whistler found himself being half-dragged back to the pier where the trouble had started and shoved into the icy water. "An' that's for trickin' me into jumpin' in the river."