David Simon had to step in to rescue the family business when he was 29 years old. Now, more than three decades later, America’s last mall king is thinking about whether his own son will be ready to take the helm.

The chief executive of Simon Property Group is battling a deadly cancer but isn’t ready to step aside. Even as he scales back his working hours to deal with his health, the notorious micromanager has never been good about giving up control.

“I’ve been kind of, you know, a domineering-type CEO,” Simon said recently in a rare interview at his New York office. “Obviously, right now, that’s impossible for me to do. I still do it occasionally.”

Simon, 63, underwent a dozen cycles of chemotherapy and two surgeries since he was diagnosed with pancreatic cancer last year. He is still receiving treatment.

A ruthless competitor, he once launched an unsolicited takeover bid for rival mall operator Taubman—while its chairman was in prison. Simon’s bid failed, but he acquired the company in a $3.4 billion deal nearly two decades later.

What does he enjoy most about his work? “Winning,” Simon said, without hesitation.

Sawgrass Mills is Simon Property Group’s most profitable property.

He is prone to yelling, and to working around the clock. He won’t think twice about calling subordinates on Saturday nights or Sunday mornings, former employees say.

These days, he has cut back the hours he spends in the office and tries to keep meetings between 10 a.m. and 3 p.m. Still, he recently called in to a board committee meeting from his hospital bed.

The eldest of his five children, Eli, joined the company in 2019 and has been taking on an ever-larger role. Earlier this year, the 37-year-old oversaw the acquisition of two luxury outlet malls in Europe.

In some ways, Eli reminds people of his father. They are both self-driven, obsessed with the mall business and hyper-detail oriented, say people who have worked with them.

But where David Simon is unafraid to chew out an employee or a competitor—“We’re going to do it this way or we’re not going to do it,” is how he described his own style—his son favors collaboration.

Eli insists he shouldn’t be underestimated because of his quieter approach. “I can be forceful when I need to be,” he said.

Eli Simon, David Simon’s eldest child, joined the company in 2019.

The decision on who will be the next CEO of the country’s biggest mall owner is up to the company’s board, and there are other candidates beyond the family. But Simon said his son has what it takes to lead the company into its third generation. “Certainly I think he should aspire to it and I think he’s capable of doing it,” he said.

For now, though, the elder Simon is still in charge. “I’m focused on taking it day by day and grinding away,” he said.

‘The ultimate micromanager’

On a recent afternoon in a suburb of Fort Lauderdale, Fla., Simon was making his way through his most profitable property, the Sawgrass Mills mall.

He waved off offers from his staff to ride in a golf cart, despite the Florida heat and his own admission that he needs to slow down.

Simon is “the ultimate micromanager” who wants to know the minutiae of every deal, said David Contis, a former president at the company.

At one point, when Contis was overseeing the sale of one of Simon’s malls, his boss kept pestering him about details. Had the buyer completed due diligence? Waived its property-review contingency? Contis pleaded with Simon: “I’m a thoroughbred, let me run.” Simon replied: “Yeah, well, I’m the jockey.”

Simon prefers to think of himself as “detail-oriented” rather than a micromanager, though he acknowledged he is a “demanding leader.” His empire spans more than 250 properties, and he controls more retail space than anyone in the world, with 206.5 million square feet across his portfolio.

Floris van Dijkum, managing director at the investment firm Compass Point Research & Trading, has walked with Simon through several of his malls and said the CEO can rattle off how much rent individual tenants are paying and how sales are performing at specific stores. “Which is just staggering,” van Dijkum said.

Simon’s knowledge of the intricacies of retail helped him profit at a time when retailer bankruptcies were leaving huge holes in malls. It started in 2016, when many retailers were folding and Simon helped purchase teen-apparel retailer Aéropostale out of bankruptcy for $243 million.

Simon Property Group and partners acquired several retailers out of bankruptcy, starting with teen-apparel retailer Aéropostale in 2016.

Simon Property Group and its partners later acquired Nautica, Eddie Bauer, J.C. Penney, Forever 21, Lucky Brand and Brooks Brothers. The investments were overall moneymakers although not every purchase was successful; Forever 21 slid into bankruptcy for a second time earlier this year.

Jamie Salter, CEO of Authentic Brands Group, which partnered with Simon Property Group in buying bankrupt retailers, credits much of his recent success to Simon. Still, he said that Simon likes to get his way.

“He doesn’t have as much energy, so he’s not yelling at me as much,” Salter said. “But he still yells a little.”

Simon said he is passionate and gets animated, but insists his outbursts are partly showmanship. “Emphasizing a point,” he called it.

A $40 billion spending spree

Simon’s father and uncle founded Melvin Simon & Associates in Indiana in 1960. They built everything from strip centers to urban shopping centers and enclosed malls, including the Mall of America in Minnesota.

When Simon joined the family business, it was cash-poor and weighed down by debt. He paused the development pipeline, unwound unfavorable partnerships and prepared the company for a public offering to generate much-needed liquidity.

In 1993, the firm put most of its properties into a new company, Simon Property Group, and went public in what was, at the time, the biggest IPO in history for a real-estate investment trust.

Herb Simon, David’s uncle; David Simon; and Melvin Simon, David’s father.

Simon became CEO two years later, at age 33. He embarked on a decadeslong buying spree, spending more than $40 billion on acquisitions.

Not every deal was successful. Initial plans announced with partners in 2005 to build at least a dozen Walmart-anchored shopping centers in China didn’t live up to expectations. Simon exited the country in 2009 at a $20 million loss after developing four malls.

But Simon’s acquisitions overall expanded the company’s geographic reach and avoided the missteps, such as overburdening his properties with debt, that felled several of the U.S.’s other family-run mall companies.

Simon fought back against the rise of e-commerce by spending billions to renovate and revamp his best malls. He replaced defunct department stores with high-end fitness centers and high-tech minigolf operators, curated luxury wings and installed upscale restaurants like Nobu.

The company’s profitability is now above 2019 levels and outpacing rivals. It has raised the quarterly dividend a dozen times since 2021.

Simon Property Group has been accused of using its leverage as the U.S.’s largest mall owner to pressure retailers into opening—or not opening—at certain properties.

Simon said the company doesn’t strong-arm retailers. “We’ve just been able to improve our bargaining position by the depth and breadth of our portfolio,” he said.

Now, with Simon Property Group’s occupancy rate of 96% approaching its all-time high, the company is also sprucing up some of its second-tier properties, which tend to pull from smaller, more suburban customer bases, such as the Smith Haven Mall on Long Island, N.Y.

Next in line

Simon said he gets the most joy these days from spending time with his six grandchildren, aged five and under.

Cancer runs in the family: His mother died at age 47, when Simon was 15 years old, after battling uterine cancer for several years. His father died of pancreatic cancer at age 83.

At first, Simon didn’t want to even look at the site of the incision from his 10-hour surgery in December, but now he shows off the long scar as a badge of honor to friends and family.

Simon has been undergoing treatment for pancreatic cancer.

Even before Simon’s diagnosis, Simon Property was working to elevate younger executives to prepare them for leadership positions. That includes Eli, who is chief investment officer.

Among his first big assignments was to spearhead the Taubman acquisition, which was announced in February 2020. The final stages of dealmaking occurred during Eli’s engagement party. In true Simon fashion, he didn’t let his personal life interfere with the job. As the event got under way, he sneaked off to hash out last-minute terms with Simon’s general counsel.

Eli says the two most important lessons he has learned from his father are to be immersed in the details and to have a mindset of an owner. “When you view every dollar as your dollar, that leads you to have really strong discipline,” he said.

Simon said his relationship with Eli is different than the one he had with his own father, whom he described as supportive but someone he learned from by observation more than direct instruction. Eli receives more guidance, Simon said, but added that he’s working to loosen the reins. “I’m going to win the argument, but I will listen,” Simon said. “Occasionally, I say, ‘OK, yeah. OK, do it your way.’ ”