Spencer Pratt says he leaked photos of teen Mary-Kate Olsen partying with Henry Winkler’s son for $50K

Long before Spencer Pratt became a reality TV lightning rod on The Hills, he says he crossed paths with another Hollywood figure who never warmed to him: Mary-Kate Olsen. In his new memoir, The Guy You Loved to Hate: Confessions from a Reality TV Villain, out Jan. 27, Pratt recounts an uncomfortable and controversial story from his teenage years involving Olsen and her then-boyfriend, Max Winkler.

Pratt writes that he attended school in Santa Monica, surrounded by well-known peers, including Olsen and Winkler, the son of actor Henry Winkler. At the time, Pratt says he wanted to direct his own film but did not have the money. That ambition, he admits, led him down a questionable path.

He describes discovering what he called a “wasted resource” in Max’s bedroom: a wall covered with photos of Olsen taken during their relationship. Pratt described the images as “young love documented in European hotels, Hollywood parties, stolen moments.”

According to the book, he encouraged Winkler to take the photos down after the breakup. “I asked Max if I could take the photos off his wall, you know, for his healing process,” Pratt wrote. “He didn’t say no, so I took that to be a yes.”

Pratt says he later went to the Winkler family home, greeted Henry Winkler on the way in, and left with the collection of photos. He ultimately sold them to a photo agency for $50,000, a sum he admits made him feel “rich” at the time. The images soon surfaced in the tabloids.

“Less than a week later there it was, evidence of my entrepreneurial genius staring back at me from the InTouch cover at a gas station: ‘TEENS GONE WILD!’ across the cover,” he wrote. He went on to describe seeing himself in the background of one of the photos and realizing that his face had become tied to the story.

“My face was now forever linked to Mary-Kate Olsen’s supposed wild phase, preserved in grocery store checkout lines across America.” Despite the backlash the photos generated, Pratt defended his actions in the memoir, writing, “When you really think about it, it was a win-win. Mary-Kate got her rebel rebrand, Max got closure.”

Olsen has never directly addressed the photo controversy, but she did mention Pratt during a 2008 appearance on The Late Show with David Letterman, recalling their time on the school soccer field. “He does not have a good temper. He walked out of a few games, he’d walk off the field,” she said.

When Letterman asked, “Were you friends with the guy or not?” she replied, “No.” Pratt also claims in the memoir that Olsen later “would weaponize that incident against me when she was feeling petty.” The Guy You Loved to Hate: Confessions from a Reality TV Villain is available now wherever books are sold.

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