Before The Hills made Spencer Pratt a household villain, he was already stirring trouble in Santa Monica, and Mary-Kate Olsen was his first casualty. In his memoir The Guy You Loved to Hate: Confessions from a Reality TV Villain, out January 27, Pratt recounts how he turned teen snapshots of Olsen into a $50,000 payday.
Pratt explains that the photos—captured during Olsen’s teenage years with then-boyfriend Max Winkler, son of Henry Winkler—were displayed in Max’s bedroom like a “photo shrine.” Describing them as “young love documented in European hotels, Hollywood parties, stolen moments,” Pratt says he asked Max if he could remove them, framing it as a favor. Max didn’t object, and Pratt took that as permission.
The future reality star visited the Winkler home, politely greeted Henry Winkler, and walked out with the collection. He sold the images to a photo agency for $50,000, money that, in Pratt’s own words, made him feel “rich” at the time.
Less than a week later, the photos appeared on an InTouch cover under the headline “TEENS GONE WILD!”—a shot of Olsen with empty bottles and a stunned Pratt frozen in the background. Suddenly, he wasn’t just the seller; he had become part of the story itself.
Looking back, Pratt frames the act as a sort of entrepreneurial win. “When you really think about it, it was a win-win. Mary-Kate got her rebel rebrand, Max got closure,” he writes. The tale reads like early evidence of the cunning and chaos that would define his career on reality TV—profitable, controversial, and entirely unapologetic.
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Last modified: January 28, 2026
