George and Leo have been polarizing figures in the financial news world for years. Often appearing on mainstream news sites like Fox News and CNBC, the relationship between these two very wealthy men is a fascinating one. When it comes to investing, they can both be considered experts. But what exactly is their relationship like? Is it a rivalry? A friendship? Or something else entirely?

A Friendship

While there are definitely people with extremely negative opinions of both men, you’ll often hear more positive things said about them. And, in many cases, this is because they genuinely like and respect one another. George, 77, and Leo, 80, worked together as teenagers at the Chicago Mercantile Exchange. Since then, they’ve remained close friends and business partners.

Leo even bought two apartments from George back in the 70s. Known as the “Sugar Barons,” the two friends became wealthy from trading sugar and have seen their net worths grow to a combined $18 billion. In fact, both men were among the top five richest people in the world as of 2019.

According to Forbes, George is now the third or fourth-richest person in the world, with an estimated net worth of $16.5 billion. His company, World Holdings, owns various businesses, including U.S. Steel and the Miami Marlins baseball team. He also has an 18.9% stake in the PGA Tour and a 7.25% stake in the Champions Tour. Additionally, George founded, and for many years was the chairman of, the American Stock Exchange, the New York Futures Exchange, and the Intercontinental Exchange. He is also a director of the Forbes 400, which Forbes defines as the “elite” among the 400 richest individuals in the world.

When it comes to investing, the two friends are often compared to Jay Gatsby and His Majesty, the King of Morocco. According to biographer Michael Steinberger, their lives “echo[ed] the wildly extravagant lives of the Roaring Twenties, only with deeper roots in the tumultuous decades that followed.” In other words, their opulent lifestyles are a reflection of the tremendous success born from decades of hard work and savvy investing.

A Rivalry

While there is some friendly competition between the two men when it comes to investments and business, it’s more common to see them jousting with one another when it comes to public opinion and rhetoric. Whether it’s supporting different candidates in the 2020 presidential election or lending their support to different causes, they often find themselves in contentious situations. For example, both are very prominent supporters of President Donald Trump, but they’ve been involved in pitched battles over the administration’s trade policies.

In May 2019, a feud between the two boiled over when George called Trump a “moron” on Instagram. A few days later, Leo went a step further and called Trump a “fucking moron.” While the two men have been friends for decades, they’ve always been comfortable expressing their opinions and acting on their convictions. These are two billionaire capitalists, for god’s sake, and their opinions don’t need to be watered down for the sake of social decorum.

Family Feud

Not only do they butt heads on the financial news landscape, but George and Leo are also famous for their acerbic public disagreements with their kids. Far from being a mere media phenomenon, this family feud appears to run deeper, with George and Leo at odds with their biological children as well. Forbes’ Steinberger notes that this “long-simmering generational conflict,” along with George and Leo’s “tumultuous past,” have made them “polarizing figures in American culture.” And, indeed, it’s often hard to find common ground when it comes to these guys. But, as with most family squabbles, there’s more than one side to this story.

Forbes rated George as the 17th most powerful person in the world in 2020 and the 4th most influential money manager in the world. In 2021, Business Insider ranked him 59th on their list of the world’s most powerful people, and 78th on their list of the world’s most influential money managers.

While some of these rankings seem high, the thing is that George isn’t messing around. He knows how to pick winning stocks and how to make the right investments. For someone of his generation, the numbers are pretty impressive.

Meanwhile, Leo’s family has seen their net worth grow to $16.5 billion, surpassing his older friend’s net worth for the first time in 2020. His four children—Margaret, Peter, Biz, and Ron—run their own significant investment firms and have become extremely successful in their own right. Peter and Ron have become involved in a legal battle over control of their father’s empire, with Ron seeking to take over operations of the companies. The patriarch still maintains a significant stake in the company, but it’s unclear whether he’ll remain involved in the day-to-day operations.

At this point, it’s clear that George and Leo’s relationship is anything but traditional. But what is it exactly? Is it a rivalry? A friendship? Or something else entirely? We may never truly know, but, as their feud continues to garner so much attention, it’s clear that their unique relationship will continue to fascinate those around them and, perhaps, even inspire others.