Jamie Oliver — The Crusading Chef ($300M)

Jamie Oliver's empire reached $300 million from The Naked Chef launch, but its collapse in 2019 marks the largest restaurant chain failure in British history, closing 22 UK restaurants and costing 1,000 jobs. Oliver personally lost $13 million, yet he pivoted to YouTube with 7 million subscribers, children's school food campaigns, and home cooking content. His eight cookbooks remain the UK's top-sellers, but the restaurant failure contrasts sharply with #6 Bobby Flay's stable food media empire. Oliver's brand survived, but this chapter proves even crusading chefs can lose millions.