You know the Bulls. You know the White Sox. But do you know the man who’s been quietly (and occasionally not-so-quietly) pulling the strings for more than four decades? Meet Jerry Reinsdorf, a billionaire owner who swapped real estate transactions for one of the most dramatic legacies in Chicago sports history.

From championship highs to fan-guided pandemonium, his tale is replete with power plays, controversy, and maybe, just maybe—the beginning of the end of an era. If you believed drama was reserved for the field only, think again!

Who is Jerry Reinsdorf? Everything you need to know about the Chicago White Sox owner

Prior to Jerry Reinsdorf being the Bulls and White Sox man behind the scenes, he was up to his knees in real estate. In 1973, he founded Balcor Company and became rich when he sold it to American Express nine years later. With millions at his disposal, he made the jump into sports—and the rest became meme-able Chicago sports history.

In 1981, Reinsdorf and his team purchased the White Sox for $19 million. Four years later, he acquired the Bulls—yes, the Michael Jordan Bulls—for $9.2 million. Jump ahead 40 years: the Bulls are now worth $5 billion, and the White Sox more than $2 billion. Reinsdorf today owns an estimated 40% of the Bulls and 19% of the Sox. Not bad for a man who says he doesn’t golf or play bridge.

Here’s the kicker: while Reinsdorf gets credit for creating the Bulls dynasty, his tenure as White Sox overlord has been much less illustrious. One World Series championship in more than 40 years. Limited playoff appearances. Fans have flown “SELL THE TEAM” signs, and with the Sox posting futility records recently, the anger is legitimate. But throughout it all, Reinsdorf remains unfazed. As he once said, “What else would I do?”

How rich is Jerry Reinsdorf? A glimpse at his sports portfolio

Let’s get to the bottom line. Reinsdorf isn’t merely a sports franchise owner—he’s a billionaire investor who’s perfected the game of long-term investing. That $19 million bet on the Sox? Now valued at more than $2 billion. That $9.2 million bet on the Bulls? It’s grown 500-fold. With controlling stakes in two of Chicago’s largest franchises, Reinsdorf’s investment portfolio is among the best.

His method? Believe that slow and steady wins the race. Reinsdorf has always preferred strategy to flash. He eschews spending on high-profile free agents or pursuing quick fixes. It’s been wonderful for his bank account—less so for the White Sox win total. In 2024, they were 23rd in the MLB payroll. In 2025? Expected to be the 29th of 30. Not surprisingly, fans aren’t exactly partying.

Off the field, Reinsdorf stays out of the limelight. He’s even said, “I’m a boring guy” (And meant it). Known more for behind-the-scenes maneuvering than social media buzz, he’s built a reputation rooted in loyalty and control. Whether fans cheer or jeer, there’s no denying his ownership has shaped the city’s sports identity for decades—and now, change may be inching closer.

A glance at his Chicago White Sox ownership: A complicated MLB legacy

Let’s be honest—Reinsdorf’s years with the White Sox have been a rollercoaster, and more recently, it’s been plummeting. Following the magical 2005 World Series run, everything fell apart. Low payrolls, disastrous front office maneuvers, and a series of miserable seasons have characterized the last two decades. The nadir? A brutal 36-126 mark in 2024.

But this is where things get really interesting: change could be in the air. Just word came out that Justin and Mat Ishbia (owners of the Phoenix Suns and Mercury) are interested in acquiring the Sox. They first tried to acquire the Minnesota Twins but stepped back—now maybe looking to Chicago. The kicker? They’re not buying from Reinsdorf but from limited partners. But.

Reinsdorf has been unequivocal—he will not sell in his lifetime. He has openly declared he will continue to own the team until he dies, after which time his family will make the determination. But if the Ishbias start hoarding shares, that could indicate a guard changing. TL;DR: There’s change on the horizon, just not suddenly. For Sox fans long frustrated with the Reinsdorf regime, this could be the initial fissure in the Reinsdorf dynasty.

Who was his wife? Meet his college sweetheart, Martyl Rifkin

Jerry Reinsdorf’s romance started at George Washington University, where he and Martyl Rifkin met in the 1950s. They were married in 1956 and spent close to 70 years together—a testament to lifetime commitment. But Martyl was more than just a loyal partner; she was a creative power behind the scenes, designing five of the Bulls’ six championship rings during the 1990s and even the Sox’s 2005 World Series ring.

Outside of sports, Martyl was a dedicated volunteer. She donated more than a million coloring books and toys to hospitals and orphanages throughout the globe, earning recognition such as the Clarence Troyer Volunteer of the Year Award. She also studied jewelry design, where she specialized in complex cloisonné work. She died in 2021 at age 85, having left behind a legacy of creativity and kindness.

Her influence wasn’t only experienced by Jerry but also by the entire Reinsdorf family. Martyl’s presence grounded their home and added a human element to a life so much dominated by big business and sports soap opera.

Jerry Reinsdorf’s family: children, legacy, and personal bonds

Jerry and Martyl formed a close family with four children: Michael, Susan, Jonathan, and David. David, unfortunately, died in 2014 at age 51. Michael took up his father’s mantle and is currently President and COO of the Chicago Bulls. Susan carried on Martyl’s charitable work, and Jonathan has remained relatively in the background.

The Reinsdorfs have always been sure to remain close, even during the storm of pro sports. Jerry frequently brings his kids and grandkids with him to games, and Martyl would sit with the grandkids for hours crafting and doing computer time. Despite all his money—$2 billion estimated—Jerry has frequently said that family is his real fortune. He might have built two of Chicago’s largest sports empires, but behind the business deals and championship banners is a man who has never lost touch with his roots or his people.

Love him or not, Jerry Reinsdorf is synonymous with Chicago sports. From Jordan’s dynasty to White Sox dysfunction, he’s been at the center of it all. And now, as whispers of a new era grow louder, one thing is certain: when his chapter finally ends, it will close one of the most defining—and debated—eras in the city’s sporting history.