Chapter 34: Taking a Big Gamble

After temporarily parting ways with the Chase couple, Margaret led Josh to meet one of the hosts of the evening's event, John Leibler.

“Good evening, my dear. I’m so glad you could make it. You’re as stunning as ever!” said the seemingly kind older gentleman, greeting Margaret warmly with a gentle hug.

Standing beside him were two men: one was David, whom Josh had encountered before—he was glaring at Josh with visible displeasure. The other man was an older gentleman, likely close in age to John Leibler.

“Thank you, Uncle John. By the way, let me introduce Josh to you—the one I mentioned before.” Margaret smiled as she gestured toward Josh.

“Good evening, Mr. Leibler. I’m Josh Kahn. It’s a pleasure to meet you,” Josh said respectfully, maintaining his composure.

“A fine young man. Enjoy yourself,” John said, giving Josh a brief, appraising look before nodding in approval and extending his hand.

The gesture was a clear sign of initial acceptance—though mostly out of consideration for Margaret, who was a close family friend.

Josh, understanding the importance of this moment, extended his hand and shook John’s firmly, expressing his respect.

“Oh, and let me introduce you to Alonzo Emery, my long-time legal associate,” John said, gesturing toward the older man beside him. As for David?

John had no intention of introducing him.

He understood his son’s nature all too well. While he wouldn’t mind if Margaret and David had shown mutual interest, it was evident Margaret wasn’t interested in David at all. There was no point in forcing the matter or embarrassing anyone—especially not as the host of this prestigious event.

David, though unhappy, wasn’t foolish enough to cause a scene. Even his hostile glares at Josh remained silent.

“Nice to meet you, young man. If you ever have any legal issues, feel free to reach out to me,” Alonzo Emery said warmly.

Unlike John’s casual attitude, Alonzo was much more enthusiastic. Lawyers in the U.S. held prestigious positions, but ultimately, they served wealthy clients. Margaret was a significant client of his, especially since she had recently received a substantial insurance payout—a case Alonzo himself had managed.

After a brief conversation and exchanging business cards with Alonzo, Josh and Margaret moved on.

At events like this, the main purpose was to meet new people and exchange contact information. Any serious discussions would happen elsewhere.

Margaret guided Josh around, introducing him to various prominent figures in Chicago’s business and political circles.

As the evening progressed, the event reached its main focus: fundraising speeches.

Since it was a war bond fundraising gala, fiery speeches from politicians were an essential part of the program.

The main speakers included Chicago’s mayor, a Democratic senator from Illinois, and a military representative.

“Josh, do you think we’ll win this war?” Margaret asked, glancing at the senator delivering a passionate speech.

“Of course. The United States will undoubtedly emerge victorious,” Josh said confidently, his knowledge of history giving him certainty.

Although Josh suspected this world might be a parallel timeline, the overall trajectory of major historical events seemed intact.

Unless this was an alternate reality like The Man in the High Castle... but even then, Josh wouldn’t worry much.

After all, he was of Austrian descent—a peculiar advantage in wartime.

In the Axis Powers, Austrians were closely aligned with Germans due to shared culture and language. Meanwhile, in the U.S., Austrians were considered victims of invasion and faced far less scrutiny than German Americans.

“How much should we contribute to the war bonds?” Margaret asked, her confidence bolstered by Josh’s certainty.

“As much as possible, if you can afford it,” Josh replied after a moment’s thought, leaning closer to Margaret.

His advice was deliberate.

At this time, war bonds were one of the safest and most lucrative investments.

The profit margin was a staggering 100%, depending on how the bonds were handled.

During World War II, U.S. war bonds were sold at 75% or 50% of their face value and matured after ten years. For example, a $100 bond could be purchased for $50, and after ten years, it would be redeemable for the full $100.

With a low inflation rate guaranteed by America’s massive gold reserves and the Bretton Woods system, these bonds were a foolproof investment.

“Do you really think it’s worth going all-in?” Margaret asked skeptically.

“Are you considering making a big move?” Josh asked, noticing her intrigued expression.

“I’m thinking we should go big,” Margaret replied.

Josh immediately understood what she meant.

Just like modern charity galas, these war bond events had a competitive edge.

The person who donated the most—or purchased the highest amount of bonds—would undoubtedly attract attention from high-ranking officials and elites.

For Margaret, this could be a golden opportunity to establish connections and elevate her social standing.

While it wasn’t realistic for her to outspend America’s wealthiest elites, she could aim to be the top donor at this specific event.

“Do you think $3 million would be enough?” Margaret asked thoughtfully.

Josh nodded after considering it.

The U.S. government issued war bonds in multiple rounds during the war. Even the wealthiest businessmen couldn’t invest millions in every round—they had businesses to run.

Three million dollars would likely secure Margaret’s spot as the top donor of this gala without straining her finances.

However, as the gala concluded and the senator announced the top donor, Josh was stunned.

“Josh Kahn—$3 million!”

The crowd erupted in applause, leaving Josh completely speechless.