The Day Frank Sinatra Saved the World

Photo: Capitol Archives

Photo: Capitol Archives

[This story was written for Round 2 of the NYC Midnight 2010 Flash Fiction Challenge. The assignment was to write a 1000-word story--in 48 hours--in the assigned genre of "Historical Fiction," with the location of "a Farm," and containing the object, "a Diamond." This scenario is one of the first that came to mind. A few hours of internet research, a day of writing, and lots and lots of cutting later, here it is. Enjoy!]

Old Blue Eyes watched the Cuban countryside roll by, decaying with stalks of sugarcane no one would harvest and the rusting husks of candy-colored cars.

Frank hated Jack for asking. He hated his own eager “Yes.” Although the President wouldn’t even visit his house (preferring clean-cut Bing’s over mobbed-up Sinatra’s), Frank would still do anything for Jack.

That snot-nosed ingrate, Bobby, he was a different story. But when Jack called, Frank was all in.

They pulled up a gravel road, lined with leafy tobacco, to a run-down farmhouse. Three other sedans idled in the driveway.

Frank tipped his hat to a shirtless geezer who smoked on the front porch, then went in.

“Let the games begin.”


Inside, two of the world’s most dangerous men sat at a card table, almost unrecognizable. Instead of fatigues, Castro wore sandals and a guayabera. Krushchev, a linen suit. They smoked Cohibas and sipped cold, sweating Cuba Libres.

Between them, in shirtsleeves, stood the unruffled UN Secretary, U Thant. Other men, translators and bodyguards, lurked in the shadows.

Two soldiers grabbed Frank, who calmly reached into his jacket and handed them his revolver.

“Welcome back to Cuba,” Castro said, rising.

“Love what you’ve done with the place.”

“Ah, ‘the Voice!’” Krushchev exclaimed. “Maybe today he is the voice of reason!”

They took their seats. Thant unwrapped a package of UN-issued playing cards, printed with world leaders’ faces.

“No illegal Cuban ones with dirty pictures of Popeye?” Frank laughed.

Thant frowned.

“OK, this is the deal,” Frank said. “Five-card stud, per Nicky’s request. Nine rounds should keep it interesting. These chips that Thant is doling out have no monetary value, unless you count the fate of the world. Win the most chips, win the game.

“If I win, that means no more missiles down here.”

“And…?” Krushchev asked.

“The United States pledges not to invade Cuba,” Thant said.

Castro nodded his approval.

“What about me?” Krushchev asked.

Frank poked Krushchev’s chest.

“You get to not look like a jackass.”

Krushchev smiled.

“You guys win,” Frank said, “You get to keep looking like tough guys. At least until we invade next month.”

Thant shook his head. “Mr. Sinatra will kindly refrain.”

“Sorry, U.”

“Enough talk,” Krushchev said. “Time to play.”


When Thant began the final deal, Castro was losing badly. Frank and Krushchev split most of the chips between them.

“So why start this?” Frank asked.

Sinatra had a ten of spades in the hole, an ace of clubs showing. Castro showed a three of hearts, Krushchev a jack of diamonds.

“Security,” Castro said. “From you. First comes the military, then the corporations follow to exploit us.”

Sinatra looked at the crumbling walls.

“Nobody takes care of the people like you do.”

Second ace for Frank. Six of hearts for Castro. King of diamonds for Krushchev.

“What about you, Nicky?” Frank asked. “Protecting the little guy?”

“Restoring the balance of power.”

“So you want to be like us?”

Krushchev flushed.

“That’s what the space rockets and everything is about, right?”

“American life is obscene,” Krushchev said.

“That don’t mean you don’t like it.”

Frank glanced at the armed soldiers when he got the second ten—the legendary “Dead Man’s Hand.” Was he pushing his luck?

Castro got the seven of clubs, Krushchev the ten of diamonds.

“You stack this deck, U?” Frank asked. “You’re going to deal Nicky here a straight flush!”

Castro folded his cards in disgust.

“An unfair hand. But Krushchev will bury you!”

“Hush, Fidel,” Krushchev said.

Frank got his third ten. Full house. Ace of diamonds for Krushchev.

Frank had to win this. But Krushchev just grinned, without even glancing at his cards. Was he hiding that thousand-to-one straight flush?

“Here’s an idea,” Frank said. “Let’s sweeten the deal a little.”

“With what?” Krushchev asked.

“Well, you guys don’t need my money, seeing as Communism pays so well. But how about something better: Me.”

“Mr. Sinatra?” Thant asked. This was beyond the UN-approved stakes. But Frank did things his way.

“I’ll defect to Cuba. What better weapon do you need? An American star who chooses to live the Communist dream…!”

The idea was only half-crazy. Yeah, Frank’s career was going again, but where to? Novelty songs and covering scruffy rock-and-rollers? His true love had left him, nuclear war was around the corner. Even the Kennedys had abandoned him.

Why not start all over again, a noble worker under a blue Cuban sky?

“And my bet?” Krushchev asked.

“Nicky, you know your heart’s not in it any more. Why don’t you defect?”

Krushchev stared at Frank wide-eyed.

“You’d be famous,” Frank continued. “Every day would be a trip to Disneyland.”

Who was Frank kidding with his little Cuban fantasy? There was no life for him down here. Castro wasn’t looking out for the little guy. He was just another kind of mob boss, looking for power. Just like Krushchev had been.

Krushchev peeked at his hole card and frowned. This was not that sputtering, shoe-banging maniac. He looked tired.

Krushchev turned his cards over.

“There will be no defections today.”

“What?” Castro exclaimed. “You fold?”

“Yes,” Krushchev said, rising to shake Frank’s hand. “We will dismantle the missiles immediately.”

“This is an outrage!” Castro shouted.

Krushchev laid a heavy hand on Castro’s shoulder.

“It’s over, Fidel.”

As they scuffled, Sinatra slipped Krushchev’s remaining downturned card into his coat pocket.

“Gentlemen,” Frank said. “Sorry to run, but I’ve got a plane to catch. You’ll work out the details?”

Back in the car, Frank pulled out Krushchev’s winning card. An exquisite portrait of Queen Elizabeth, gazing upon a red diamond.

So Nicky was out of the game, after all. One less mob boss in the world. There was still Castro to deal with, and, yeah, maybe the Kennedys, too.

But Frank had saved the world for at least one more day.

And that was as much as one man could do.

Even Frank Sinatra.

“We’re done here,” Frank said to the driver. “Let’s go home.”