Selling Jessica Simpson

How the pop star lost her billion-dollar fashion empire—and spent two years clawing it back

- Stephanie Clifford and Eliza Ronalds-Hannon

Of all the ways Jessica Simpson had imagined taking back control of her fashion empire, lying on a hospital bed with severe bronchitis, on a breathing machine, while 34 weeks pregnant with her third child, a daughter, was not one of them. “Her oxygen levels were dropping. I couldn’t breathe,” recalls Simpson of the harrowing, rather impractical moment in early 2019 when she and her mom, Tina, president of the business, decided to initiate a takeover bid. “I was 260 pounds. She was a very big baby. We were like, ‘Just take her out.’ ”

Her daughter Birdie didn’t end up being delivered that day (doctors were able to stabilize her), but that moment did mark the beginning of a two-year battle for control of Simpson’s namesake brand, the rare celebrity line to break $1 billion in sales. “We’ll borrow against our homes,” says Simpson of her resolve. “Even if I have to go live in a little, tiny place in Ireland, I will.”

When Simpson started the line in 2005, she was an improbable apparel mogul. The gospel-singing daughter of a Baptist pastor, she first surfaced on the pop-music scene in the 1990s, a new breed of sexy teen blond belters alongside Britney Spears and Christina Aguilera. Although she had the vocal chops, it was the pioneering 2003 hit MTV show Newlyweds, a voyeuristic romp through the then-23-year-old’s new marriage to her boy-band husband, Nick Lachey, that vaulted her into the pop culture firmament. Those who’d written her off as merely a ditzy entertainer became converts. Her viral malapropisms, frank charm, and sexy Texas style drew an Instagram-like following years before the social platform even existed.