THE CHICACO RUN OF 32

The summer of 1932 scorched Chicago, where the Democratic National Convention thrummed with raw ambition, deceit, and danger. Jesse Spalding, Howardstown’s sharpest politician and whiskey dealer, stood at the heart of the storm, his eyes burning with dreams of power. His special recipe whiskey, smoother than a summer breeze, was the obsession of Chicago’s underworld. With Al Capone locked away in Alcatraz since 1931 for tax evasion, mob bosses like Lucky Luciano and Frank Costello turned to Jesse to flood the convention with Howardstown’s finest, aiming to loosen delegates’ tongues and sway votes to crown Franklin D. Roosevelt as the Democratic nominee.

Back in Howardstown, the air was thick with the tang of mash and the hum of desperation. Distillers, faces haggard from sleepless nights, toiled in sweltering sheds, their stills glowing like hellfire to meet the mob’s colossal order. Barrels piled high, each one a promise of profit and influence. Jesse, pacing the creaky warehouse floor, his boots kicking up dust, barked orders with a voice hoarse from urgency. “Faster, boys—this whiskey’s our ticket to the big leagues!” he shouted, his mind racing with visions of shaking hands with the next president. His wagons, groaning under the weight of casks, rumbled toward Chicago, each mile a gamble through backroads crawling with risks—bandits, rivals, or worse, Prohibition agents.

Jesse’s oldest friend, Kentucky Governor A.B. “Happy” Chandler, saw the same glittering prize: a chance to climb into FDR’s inner circle. Happy, with his wide grin and sharper cunning, leaned hard on his political clout to shield Jesse’s operation. He strong-armed sheriffs, bribed deputies, and sweet-talked feds to keep the roads clear. “No one touches Jesse’s run,” he growled, his drawl masking a ruthless edge as he ensured the whiskey flowed north without a hitch. In smoky Kentucky taverns, Happy toasted Jesse’s nerve, clinking glasses filled with their special recipe. “This’ll put us at the table with FDR,” he said, his eyes alight with ambition.

Chicago was a tinderbox, its convention halls choked with cigar smoke and scheming. Luciano and Costello, shadowed by Tammany Hall’s Albert Marinelli, prowled the crowds, their pockets heavy with mob cash and Howardstown whiskey. Delegates drank deeply, their laughter echoing over the clink of glasses as Marinelli, after tense backroom deals lit by flickering lamps, swung New York’s votes to FDR, sealing his nomination. Jesse and Happy worked the floor like seasoned hustlers, their whiskey the lifeblood of every handshake, every whispered pact. The special recipe flowed like a river, loosening lips and forging alliances under the mob’s watchful eyes. Luciano, his sharp gaze cutting through the haze, nodded approval as the delegates swayed to his tune.

But FDR was no pawn. From the convention stage, his voice roared like thunder, denouncing corruption and glaring at Tammany’s mobbed-up crew with righteous fury. Jesse’s heart pounded, his palms slick with sweat as he caught the fire in FDR’s eyes. “Happy,” he hissed, pulling his friend into a dim corner, the din of the crowd muffling his words, “FDR’s playin’ his own game—he’ll burn us all if we’re not careful.” Happy’s grin faltered, his mind racing. They’d bet big on the mob’s influence, but FDR’s words were a warning shot—this was a man who’d sooner dismantle Tammany than dine with it.

As FDR clinched the nomination, the air shifted. He turned on Tammany with a vengeance, vowing to crush their graft with investigations that sent shockwaves through Chicago’s underworld. Luciano’s eyes blazed with betrayal, his empire teetering as federal agents closed in. Costello, ever the pragmatist, slipped into the shadows, but the heat was on. Jesse and Happy, quick as foxes, saw the noose tightening and moved to save themselves. “We’re just whiskey men, nothin’ more,” Jesse swore, his voice steady despite the chaos, brushing off mob ties like dust from his coat. Happy, ever the politician, flashed his governor’s smile, spinning tales of Kentucky hospitality to keep his reputation spotless.

In the aftermath, FDR stood untouchable, his New Deal vision rising above the convention’s sordid underbelly. The mob faced the law’s wrath, with Luciano and his crew scrambling to dodge indictments. Jesse’s whiskey, though, kept flowing to speakeasies from New York to New Orleans, his pockets bulging with profits. Howardstown’s name became a whispered legend in backrooms and bars. Happy, unscathed, basked in Kentucky’s political glow, his governor’s seat secure. They’d danced on a razor’s edge, their Chicago run a high-stakes gamble that could’ve ended in ruin. FDR never knew the connection so Jesse and Happy walked away, hearts pounding, free from the mob’s collapsing shadow.