The back room of Giancana's favorite Chicago steakhouse was a shrine to mobster cliché. The walls were paneled in dark, almost black, wood, scarred with decades of cigar smoke. A massive, mounted swordfish with dead, glassy eyes hung on one wall. The air was thick with the smell of stale smoke, expensive whiskey, and a palpable, simmering menace. This was Sam Giancana's throne room, his personal court, and he was its absolute, undisputed king.
He sat at the head of a large, round table, a half-empty bottle of bourbon at his elbow. He was radiating a volcanic, barely contained rage. He felt betrayed, used, and, worst of all, disrespected by the Kennedy brothers he had helped put in power. And now, the fancy, mysterious suit who had been the architect of the whole damn deal was coming here, to his city, to see him. Giancana saw it as an act of either supreme arrogance or supreme stupidity. Either way, he was looking forward to killing the man.
He was flanked by his two most dangerous enforcers, silent, brutish men who watched the door with the dead-eyed patience of crocodiles. The atmosphere was not that of a meeting; it was an ambush in waiting.
The door opened, and Ezra Prentice entered the room. Alone.
He was a creature from another planet in this den of crude power. His dark, tailored suit was a whisper of quiet expense, his shoes gleamed, and he moved with a calm, unhurried grace that was an insult in itself. He did not look afraid. He did not look intimidated. He looked like a university professor who had accidentally wandered into the wrong room.
He walked to the table but did not sit in the empty chair that had been offered. He remained standing, a deliberate choice that subtly denied Giancana the status of a host. He looked at the mob boss, his expression one of mild, analytical curiosity.
"Mr. Giancana," he began, his voice quiet but carrying an incredible authority that cut through the thick, menacing atmosphere. "Thank you for seeing me. I am here because you have become a problem. You are loud, you are sloppy, and you have violated the terms of our agreement. This is an unacceptable failure of professional discipline."
The sheer, breathtaking audacity of the statement stunned the room into silence for a moment. Then, Giancana exploded. He leaped to his feet with a roar of pure, animalistic fury, his chair crashing backward onto the floor.
"You son of a bitch!" he screamed, his face turning a dark, mottled purple. Spittle flew from his lips. "You and your pretty boy Kennedys! You use me to do your dirty work, and then that little bastard brother tries to put me in jail! You think you can walk in here and talk to me like that?"
His enforcers, Johnny Roselli and Santos Trafficante, instinctively reached for the pistols holstered under their coats. The air crackled with the imminent promise of violence.
Ezra did not flinch. He did not raise his voice. He did not even look at the two gunmen. He simply waited, his calm gaze fixed on Giancana, letting the mob boss's rage crash against the granite wall of his composure and recede.
When the screaming subsided, replaced by a heavy, ragged breathing, Ezra began his attack. It was not an attack of force, but of quiet, devastating omniscience.
"You have a mistress," Ezra said, his voice as calm and steady as a surgeon's scalpel. "A showgirl in Vegas. Her name is Phyllis. Last Tuesday, you wired fifty thousand dollars from a Teamsters pension fund account to a shell company, 'Nevada Novelties,' which is registered in her sister's name. It was a clear, foolish, and sentimental violation of our financial protocols."
Giancana stared, his jaw slack, the rage on his face beginning to morph into stunned disbelief. How could this man possibly know that?
Ezra continued, his voice relentless. "You have significant, undeclared gambling losses. A debt of two hundred thousand dollars to the Cleveland crime family, a result of a series of bad bets on the '59 World Series. A debt you have been hiding from your own people, and from Mr. Lansky. A sign of poor discipline and a significant vulnerability."
The color drained from Giancana's face. He was no longer a raging bull; he was a man being systematically, psychologically dissected in front of his own men.
Ezra delivered the final, killing blow. "And, most foolishly of all, you have been speaking of our arrangement. You have spoken of it to your mistress. You have spoken of it to your associates. And you have spoken of it on your own telephone, a telephone which you, a man in your position, should have had the basic intelligence to know has been bugged by the Federal Bureau of Investigation for the past five years. Your ego, Mr. Giancana, has compromised my operation, it has endangered the President of the United States, and it has put a noose around your own neck."
Sam Giancana was a broken man. His rage had evaporated, replaced by a cold, creeping, existential fear. This quiet man in the expensive suit knew everything. He had seen into the deepest, most secret corners of his life. He was not a suit. He was a demon.
Ezra now laid out his terms. They were not a negotiation. They were a series of commands.
"First," he said, his voice now a blade of ice. "Operation Mongoose is terminated, effective immediately. Your services in Cuba are no longer required."
"Second," he continued, "you will never again speak of your involvement with my organization or with the Kennedy administration to anyone. Not to your mistress, not to your men, not to a priest in a confessional. If I hear even a whisper, the complete, documented evidence of your financial crimes—evidence far more detailed than anything the FBI possesses—will be delivered not to the government, but to your rivals in New York and your creditors in Cleveland. I imagine they would be most interested."
"Third. In return for my silence, you and your organization now work for me. Not as a partner. Not as an ally. You are now a wholly-owned asset. When I require a service, a piece of information, an action, you will provide it. Quietly and without question."
He paused, letting the new reality sink in, the new chains settle around Giancana's soul.
"And finally," Ezra said, "the matter of Robert Kennedy. You will instruct your lawyers to begin cooperating with his investigation. You will sacrifice a few of your non-essential lieutenants, men who are already a liability to you. You will accept a plea bargain on a lesser charge—tax evasion, perhaps. It will give the Attorney General his public victory, and it will end his crusade against you personally. I will use my own influence to ensure the sentence is minimal, and the prison comfortable. You will be a martyr for a short time, and then you will be free."
Sam Giancana, the feared and brutal boss of the Chicago Outfit, a man who had killed with his bare hands, had been completely, utterly outmaneuvered and dominated. He had been stripped of his power, his secrets, his very will, by a quiet man with a file. He had no choice. He sagged back into his chair, a deflated balloon of a man.
"Alright," he croaked, his voice a hoarse whisper. "Alright. I'll do it."
Ezra had not just silenced the threat; he had subjugated it. He had taken ownership of one of the most powerful and dangerous men in the country. He gave a single, curt nod, turned his back on the broken mob boss, and walked out of the lion's den, leaving a new, more terrifying king in his place.