Real estate billionaire David Simon is facing a make-or-break moment whether he can reinvent his mall business with a controversial bet on JCPenney
Real estate titan David Simon is set alongside another large landlord to acquire JCPenney's brand and operations, including 550 stores it owns or leases. It's Simon's largest push yet beyond owning malls into possessing the retail businesses that occupy them, a divide few owners have crossed.
Mounting a turnaround of JCPenney, which has eluded a string of CEOs and the hedge-fund billionaire Bill Ackman, will test Simon's ability to juggle conflicting roles and his strategy to reinvigorate a mall business threatened by bad news from changing consumer habits, to the rise of e-commerce, and, in recent months, a global pandemic.
Business Insider spoke with more than a dozen people who know and have worked with Simon to learn more about the press-shy mall king and his career make-or-break moment. They described a savvy, ultracompetitive CEO who so far has made prescient moves, steering his company into safer and forward-thinking investments as the US was reaching mall oversaturation.
But some also pointed to Simon's winner-take-all mentality and sharp elbows as a potential liability as he increasingly relies on partners and a more collaborative relationship with tenants.