[November 1932 - Sterling Enterprises Temporary Headquarters]
Three years. Three years of strategic acquisitions, careful maneuvering, and playing the prophet without being too obvious about it. Alexander Sterling, now eighteen and finally looking it, sat across from Johnny Torrio in what would soon be the executive floor of Sterling Tower.
The former Chicago Outfit boss looked like retirement hadn't quite taken—sharp suit, sharper eyes, and the kind of presence that made rooms rearrange themselves around him.
"You sure about this, kid?" Torrio asked, examining the contract with eyes that had seen every scam since Moses parted the Red Sea. "I'm flattered by the offer, but I'm retired. Out of the game."
Alexander leaned back in his chair, channeling the confidence of someone who'd already lived this conversation in his head a thousand times. "Mr. Torrio, you ran Chicago's underworld like a Fortune 500 company before Fortune had 500 companies to list. I'm offering you the chance to do the same thing legally."
"Legally?" Torrio's laugh had rust in it. "Kid, legality's like virginity—once it's gone, it don't come back."
"No, but it can be convincingly faked with the right paperwork." Alexander slid a folder across the desk. "I need someone who understands logistics. Distribution. Managing personnel who might have... flexible relationships with conventional morality."
"You mean criminals."
"I mean entrepreneurs with alternative approaches to market penetration."
Torrio's smile could have cut glass. "That's the fanciest way anyone's ever called me a crook."
"You're not a crook, Mr. Torrio. You're a businessman who operated in an industry that happened to be illegal. Now I'm offering you the chance to apply those skills to industries that are mostly legal."
"Mostly?"
"Well, creative interpretations of interstate commerce laws may be required. Flexible understanding of tax codes. Innovative approaches to union negotiations."
"So, crime with better PR."
"Crime is such an ugly word. I prefer 'aggressive regulatory arbitrage.'"
Torrio actually laughed at that, a genuine sound. "Christ, kid. You've got balls. But why me? Why not some Harvard boy with clean hands?"
"Because Harvard boys think inside boxes that you don't even know exist. Because they'd see obstacles where you see opportunities. And because..." Alexander leaned forward, "when Prohibition ends—which it will, within the year—a lot of your former colleagues are going to need new employment. I'd rather have them working for me than against me."
"Smart. Speaking of former colleagues... what about Al?"
"Already in motion." Alexander's smile was sharp. "Amazing what proper medical treatment can do for a man's... legal situation. Especially when certain judges owe favors to certain investment firms."
"You're getting Capone out?" Torrio's eyebrows rose. "Kid, that's..."
"Ambitious? Dangerous? Exactly the kind of move that signals to everyone else that Sterling Enterprises plays for keeps?" Alexander stood, moving to the window. "Mr. Torrio, I'm building something here. Something that'll last longer than any government, any law, any moral fashion. But I need people who understand that business is war by other means."
"And if I say no?"
"Then you enjoy your retirement, and I find someone else. But we both know you're bored. We both know you miss the game. The only difference is, my game has better retirement benefits and significantly less chance of dying in a hail of bullets."
Torrio was quiet for a long moment. Then: "What about the old country? I still got connections there."
"Funny you should mention that. I have some interesting plans for European expansion. Particularly in industries that might soon be very concerned with... aggressive political changes."
"You mean the fascists."
"I mean emerging markets with unique opportunities for those willing to navigate complex political situations."
"Christ, you even make fleeing Mussolini sound like a business opportunity."
"Everything's a business opportunity if you squint right."
Torrio stood, extending his hand. "Alright, Sterling. You got yourself a CEO of Strategic Operations. God help us both."
They shook on it. Alexander had just hired one of the most dangerous men in America to run his legally-adjacent operations.
Phase one complete. Now for the really fun part.
[Two Days Later - Tombs Prison, New York]
Al Capone looked like death warmed over and served cold. The syphilis was eating him alive from the inside, but his eyes still held that dangerous intelligence that had made him king of Chicago.
"Johnny says you got a proposition," Capone wheezed, his hands shaking slightly. The tertiary stage was setting in. Without treatment, he had maybe eight years. With treatment...
"I can get you out," Alexander said simply. "Get you cured. Get you rich. Legally."
Capone laughed, which turned into a coughing fit that sounded like his lungs were trying to escape. "Kid, I got eleven years. Federal time. You know what that means?"
"I know it means you'll be dead in eight without treatment. I know it means your empire's already crumbling without you. And I know that three judges on the appellate court have recently discovered their investment portfolios are worth considerably more than they expected."
Capone's eyes sharpened. "You're saying you bought judges?"
"I'm saying I made strategic investments in judicial retirement funds. What grateful judges do with their newfound financial security is between them and their god." Alexander pulled out a medical file. "Penicillin. My pharmaceutical division's been working on it. Cure rate for syphilis is nearly perfect if caught in time. Which yours barely is."
"Penicillin ain't even on the market yet."
"Perks of vertical integration. I own the labs doing the testing."
Capone was silent for a moment, processing. Even dying, his mind was sharp. "What's your angle, kid?"
"I need someone who understands distribution networks. Supply chains. Personnel management in... challenging environments. Prohibition's ending, Mr. Capone. But the skills you developed? Those translate beautifully to legitimate enterprise."
"What makes you think I won't just kill you once I'm out? Take over your whole operation?"
"Because you're a businessman, not a mad dog. And because I'll have saved your life. And because..." Alexander smiled, "by the time you're out, I'll be too valuable to kill. My operations will be your operations. My success will be your success."
"You're awful confident for a kid."
"I'm awful confident for anyone. But I've been right about everything so far. The crash. The depression. Roosevelt's election. Want to bet against my streak?"
Capone studied him with the intensity of a man who'd survived by reading people. "What exactly would I be doing in this legitimate enterprise?"
"Running my Midwest distribution network. We're moving into beverages—positioning for Prohibition's repeal. Also shipping, trucking, some light manufacturing. All the fun of your old job with none of the Thompson submachine guns."
"And if I want to bring some of my boys?"
"As long as they can pass a background check that we write, I don't care if they used to be choir boys or killers. Results matter. Methods are negotiable."
"You're something else, Sterling. Can't decide if you're a genius or crazy."
"Por que no los dos?" Alexander stood. "Six months, Mr. Capone. Treatment starts next week during your medical evaluations. The appeals process is already in motion. By summer, you'll be a free man with a clean bill of health and a corner office."
"And if this is all bullshit?"
"Then you die slowly in prison and I wasted some money on judges. But we both know I don't waste money."
Capone extended his hand through the bars. "Get me out and healthy, kid, and you've got yourself a deal."
"Pleasure doing business with you, Mr. Capone. Welcome to Sterling Enterprises. Try not to kill anyone on company time."
"No promises."
"I'd be disappointed if you made any."
[December 1932 - Stark Industries Boardroom]
Howard Stark Sr. looked like prosperity had personally betrayed him. His company was hemorrhaging money faster than a hemophiliac in a knife factory. His sons, Howard Jr. and Edward, flanked him like pallbearers at capitalism's funeral.
"Mr. Stark," Alexander began, sliding a check across the table. "Three million dollars for thirty percent of Stark Industries."
"That's... that's insulting," Stark Sr. sputtered. "Before the crash, we were worth—"
"Before the crash, I was in middle school. We're not living in before. We're living in now. And now, your company needs capital more than pride."
Howard Jr.'s jaw clenched. Even at twenty-five, he had that Stark genius evident in his eyes. And that Stark pride evident in his posture.
"What's to stop us from finding other investors?" Howard Jr. challenged.
"Nothing. Except time. Which you don't have. Three months until bankruptcy, by my calculations. Maybe four if you fire more workers. But then you won't have anyone to build your brilliant designs, will you?"
"How could you possibly know our financial situation?"
"Because I do my homework, Mr. Stark." Alexander pulled out another folder. He was getting good at the folder reveal. Very dramatic. "Every patent, every contract, every outstanding invoice. Your company is brilliant. It's also broke. I'm offering to fix one of those problems."
"At highway robbery prices," Edward interjected.
"At depression prices. Which, yes, are basically highway robbery. But the highway's legal and the robbery comes with a check."
They negotiated for two hours. Alexander let them talk him up to 3.5 million—exactly what he'd planned to pay anyway. The art of negotiation was letting the other side think they'd won.
"There is one condition," Alexander added as they prepared to sign. "If Stark Industries develops any technology with military applications, Sterling Enterprises gets right of first refusal on manufacturing partnerships."
"We're not a weapons company," Howard Jr. said.
"Not yet," Alexander smiled. "But horizons change. Wars especially have a way of expanding them. Better to have the contracts in place before the shooting starts."
The Starks exchanged glances at the mention of war, but signed anyway. They needed the money too badly to worry about hypothetical futures.
If only they knew how unhypothetical that future was.
[January 1933 - Sterling Tower Construction Site]
Alexander stood in the skeleton of what would become Sterling Tower, watching welders work like fireflies in the steel web. Torrio appeared beside him, moving silently despite his age.
"Capone's treatment is working," Torrio reported. "Doctors say he'll make a full recovery. The appeals process is moving faster than expected. Your judicial investments are paying off."
"Good. We'll need him operational by summer. What about our other acquisitions?"
"Electric Boat is ours. Management was so desperate they'd have sold to the devil himself."
"They did. I was just wearing a better suit." Alexander turned from the construction. "What about Bethlehem Steel?"
"Harder. They've got pride."
"Pride's expensive in a depression. Make them an offer that acknowledges their importance while emptying their pockets. Let them keep their dignity if it means we get their infrastructure."
Torrio nodded. "You know, Sterling, most eighteen-year-olds are worried about dames and dancing."
"Most eighteen-year-olds don't have a timeline to beat."
"Timeline?"
"Just an expression." Alexander pulled out a map marked with red pins. "Start looking into these oil fields. Quietly. Use shell companies."
"Texas? That's wildcatter territory."
"For now. But I have a feeling about Texas oil. Call it intuition."
Call it knowing exactly where the Spindletop successors are about to hit.
"Your intuition's been expensive but accurate so far."
"That's the best kind of intuition. The profitable kind."
Torrio studied him. "You know, kid, sometimes you talk like you've already lived through all this. Like you're remembering instead of predicting."
Alexander's blood chilled, but he kept his voice steady. "Maybe I just pay attention to patterns others miss."
"Maybe. Or maybe you made a deal with something that gave you tomorrow's newspaper."
"If I had tomorrow's newspaper, would I waste time with business? I'd be at the track making real money."
Torrio laughed. "Fair point. What about the European situation? Getting interesting over there."
"It's about to get a lot more interesting. Start identifying assets we might want to... relocate. Scientists especially. The smart ones will want to leave before the invitation becomes mandatory."
"You're talking about the Jews."
"I'm talking about anyone with brains enough to see what's coming and skills enough to be useful. Religion's irrelevant. Talent isn't."
"Cold way to look at it."
"Practical way to look at it. Sentiment is expensive. Results are profitable."
That night, Alexander stood in his office, looking over contracts and calculations. Three years since the crash. Three years of building on the ashes of other men's dreams.
Sterling Enterprises was becoming what he'd envisioned—a corporation with tentacles in every profitable industry, legitimate enough to avoid scrutiny, flexible enough to adapt to any situation.
By the time the war came, they'd be indispensable. By the time the heroes arrived, they'd be untouchable. By the time the real threats emerged, they'd be ready. Hopefully.