Teen blackmailed with inappropriate pictures, Milwaukee man reaches plea deal

OCONOMOWOC, Wis. – A Milwaukee man accused in 2023 of befriending a teen girl online, convincing her to share inappropriate photos and then threatening to leak those photos if she didn’t meet up with him reached a plea deal with prosecutors.

Benjamin Oswald, 25, pleaded guilty to using a computer to facilitate a child sex crime. As part of a plea deal with prosecutors, charges of exposing genitals and threatening to communicate derogatory information were dismissed.

According to a criminal complaint, Oswald claimed he was 18 years old and sent a Snapchat friend request to a girl who said she told him she was 14 years old. After accepting the friend request, the victim said she immediately started getting Snapchat messages from this person.

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Prosecutors said Oswald used fake names and threatened to distribute inappropriate pictures of the victim if she did not meet him at an Oconomowoc park. The complaint said the victim initially claimed she didn’t send photos to Oswald, but later said she did because Oswald told her he would “give her drugs and money” in exchange for them.

The victim later stopped responding to Oswald, prosecutors said, after Oswald kept trying to get her to meet up. She blocked him on Snapchat, but got a new friend request from him using a different name the next day. The complaint said Oswald told the victim he would send drugs or alcohol if she met up with him, but the victim told him not to contact her anymore and warned that he would be blocked. Prosecutors said Oswald then threatened to post the inappropriate photos online.

Oconomowoc Police Department

Prosecutors said the victim was also threatened with the leak of the photos if she didn’t re-add him on Snapchat again after blocking him. According to the complaint, Oswald then gave her a deadline to meet him at an Oconomowoc park, telling the victim if she “didn’t show up, she would regret it.” The victim told police he proved he had the inappropriate photos of her by sending them to her friend. The victim contacted the police to report the harassment and “admitted she was not initially truthful” with officers “because she was afraid she would get in trouble.”

The complaint said the victim’s grandfather chased Oswald’s vehicle after they found him waiting at the Oconomowoc park. The victim, a passenger in her grandfather’s vehicle, was able to identify Oswald as the driver of the car waiting at the park because he “would frequently send her” inappropriate pictures, the complaint said.

The victim said her grandfather got out and tried confronting Oswald, but he sped off. They were all eventually stopped by police.