Spencer Pratt Admits in Memoir to Selling Private Teen Photos of Mary-Kate Olsen for $50,000

In his newly released memoir ‘The Guy You Loved to Hate: Confessions from a Reality TV Villain,’ Spencer Pratt reveals a controversial incident from his teenage years in Santa Monica, California. While attending school with celebrity peers, including Mary-Kate Olsen and her then-boyfriend Max Winkler (son of actor Henry Winkler), Pratt aspired to direct his own film but lacked funding. After Olsen and Winkler broke up, Pratt noticed a collection of personal photos of the couple on Winkler’s bedroom wall, which he described as documenting ‘young love’ in various settings like European hotels and Hollywood parties. Claiming he was helping his friend with the ‘healing process,’ Pratt took the photos without explicit objection from Winkler. He then sold them to a photo agency for $50,000, using the money toward his film project. The images quickly appeared in tabloids, including an InTouch cover story headlined ‘TEENS GONE WILD!,’ portraying Olsen’s supposed wild phase with alcohol and partying. Pratt noted that one photo included himself in the background, linking him publicly to the scandal. Despite potential backlash, Pratt defends the action in the book as a ‘win-win,’ suggesting it gave Olsen a ‘rebel rebrand’ and provided Winkler closure. Olsen has not directly commented on these recent claims, though she previously expressed negative views about Pratt during a 2008 Late Show appearance, stating they were not friends and criticizing his temper during school soccer games. The memoir, released January 27, 2026, details Pratt’s pre-fame experiences and his rise as a reality TV figure on The Hills.