Kanye West — Yeezy

At its peak, Yeezy generated $1.7 billion in annual revenue, making Kanye the richest Black American in history with a $6.6 billion net worth, per Bloomberg. After his antisemitic comments, Adidas terminated the partnership, Gap followed, and he lost roughly $1.5 billion in a single day—the fastest personal wealth destruction in modern history. Unlike #2 Jay-Z's steady empire, Kanye's cautionary tale shows how a guaranteed legacy can be torpedoed by controversy. Even today, the remaining Yeezy brand holds hundreds of millions.