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Teen blackmailed with inappropriate pictures, Milwaukee man reaches plea deal

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Teen blackmailed with inappropriate pictures, Milwaukee man reaches plea deal


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.

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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.

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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

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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. 

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‘We’re still struggling’: Milwaukee mom seeks help after historic flooding as Christmas approaches

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‘We’re still struggling’: Milwaukee mom seeks help after historic flooding as Christmas approaches


MILWAUKEE — Wisconsin has confirmed a new 24-hour rainfall record after more than a foot of rain fell in Milwaukee during historic summer flooding, but for some families like Victoria Kiepert’s, the damage never ended.

The August 9th and 10th storms brought 14-and-a-half inches of rain to northwest Milwaukee in just 24 hours, now officially the most rain ever recorded in a single day in Wisconsin. Behind that historic number are families still trying to rebuild as Christmas approaches.

“We lost all of our stuff in the basement,” Kiepert said.

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Victoria Kiepert lost everything in the floods in August.

Floodwaters damaged Kiepert’s northside home, destroying nearly everything her family owned. She applied for help, but says months later, recovery is still falling on her shoulders.

“Beds, appliances, all that stuff, kids’ clothes, TVs, everything,” Kiepert said.

The Milwaukee mother, who cares for five children, says her family was left homeless for two weeks after the flooding.

Victoria Kiepert cares for five people in her home, she says she needs beds, clothing and dressers for her kids.

Victoria Kiepert

Victoria cares for five people in her home, she says she needs beds, clothing and dressers for her kids.

“We had to move, and I couldn’t find a house right away, so we were homeless for two weeks, and then we moved and still don’t have the things we need,” Kiepert said.

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Watch: Milwaukee mom seeks help after historic flooding as Christmas approaches

Milwaukee mom seeks help after historic flooding as Christmas approaches

Climate experts say the storms were unprecedented, with rain falling one to three inches an hour for several hours, overwhelming basements, streets, and sewer systems. Radar estimates show 10 to 12 inches fell across northern Milwaukee and northeast Waukesha counties, confirming the devastation was widespread.

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Kiepert says she and her kids have to sleep on air mattresses, and the holidays only add more pressure to an already overwhelming situation.

“People think that after people get FEMA money, it’s just done and over with, and that should be enough, but it’s really not because it takes months, even years, sometimes when you’re starting all over,” Kiepert said.

She’s unsure how she will provide gifts for her kids this Christmas, her family still needs basic necessities months after the flooding.

Victoria's family is hoping for a Christmas miracle.

Victoria Kiepert

Victoria Kiepert’s family is hoping for a Christmas miracle.

“We still need beds, dressers, kids’ clothing, a lot of stuff,” Kiepert said.

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As Wisconsin marks a new chapter in climate history, families like Kiepert’s say recovery can’t stop at statistics, especially as Christmas approaches.

“This year’s really hard, because mostly because of the flood, cause all the stuff we lost, I have to buy them new stuff, because that money isn’t available for Christmas,” Kiepert said.

The flooding has made this Christmas particularly challenging for Kiepert’s family, including her youngest daughter experiencing her first Christmas.

“This is my daughter’s first Christmas, it would help for all my kids but mainly for her, to make like a Christmas miracle for them,” Kiepert said.

Despite the hardships, Kiepert maintains perspective on what matters most during the holidays.

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“Sometimes it’s not about the gifts, it’s about being stable and having family around,” Kiepert said.

As Victoria’s family continues to rebuild, community support can make a real difference. A GoFundMe is available for those who wish to donate money or provide much-needed household items. If you can donate any of the furniture items she seeks, her email is Victoria.kiepert@icloud.com, or you can reach out to me by email at gideon.verdin@tmj4.com, and I will connect you with Victoria.

This story was reported on-air by a journalist and has been converted to this platform with the assistance of AI. Our editorial team verifies all reporting on all platforms for fairness and accuracy.


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Tips for Milwaukee Mitchell holiday travelers: Don’t bring wrapped gifts

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Tips for Milwaukee Mitchell holiday travelers: Don’t bring wrapped gifts


Security officials at Milwaukee’s Mitchell International Airport offered advice for passengers navigating the busy holiday travel season this December.

Tim Goodman, Wisconsin assistant federal security director at the Transportation Security Administration, said Dec. 19 that the agency is prepared for high passenger volume at Milwaukee Mitchell in the next two weeks.

Goodman said the airport expects to process as many as 12,000 travelers during the busiest holiday travel days. These dates are projected to see the most traffic:

  • Sunday, Dec. 21
  • Monday, Dec. 22
  • Tuesday, Dec. 23
  • Sunday, Dec. 28
  • Monday, Dec. 29
  • Tuesday, Dec. 30

Here’s what to know about holiday travel at Milwaukee Mitchell this year:

Arrive early, especially for morning flights from Mitchell Airport

Goodman recommended travelers arrive no later than 90 minutes before their flight takes off, and longer if they’re boarding early morning flights.

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Mornings are the busiest time of day for the airport, Goodman said.

“We are at capacity at the early morning hours,” he said. “We may see as many as 2,000 passengers going out before 7 a.m. on our busiest days.”

Don’t forget your Real ID when traveling through Mitchell

This is also the first winter holiday season after TSA began enforcing Real ID requirements for domestic flights. Starting on May 7, 2025, all domestic passengers must present a Real ID-compliant drivers license or other other acceptable forms of identification.

Earlier this month, TSA announced it will charge passengers $45 if they do not present a Real ID or other accepted identification starting Feb. 1, 2026.

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In Wisconsin, Real ID-compliant drivers licenses are marked with a star in the upper right corner. More information about how to obtain a Real ID is available on the Wisconsin Department of Transportation’s website.

Goodman said 97% of Wisconsin passengers already have a Real ID. Those who don’t have proper identification will see longer waits and additional screening at security checkpoints.

A list of acceptable identification is available on TSA’s website.

Some holiday items may not get through security at Mitchell

Goodman said some common holiday items should not be put in carry-on bags since security officials struggle to open and inspect them.

Those items include snow globes and wrapped gifts. Goodman recommended any gifts instead be put in a gift bag.

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Goodman also said passengers should completely empty bags before packing them for a flight. It’s common for travelers to forget to remove prohibited items in their bag, only to find themselves stopped at security checkpoints.

Forecast looks clear, but weather is always a ‘wild card’

Goodman said the current weather forecast shows no significant winter storm activity, but that could change closer to the holidays.

“We can plan for everything else,” Goodman said. “The weather is always the wild card.”

Goodman also said severe weather at popular hubs like Chicago and Minneapolis could impact flights at Milwaukee Mitchell.



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A federal jury finds Milwaukee judge guilty of obstructing immigration agents

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A federal jury finds Milwaukee judge guilty of obstructing immigration agents


Milwaukee County Circuit Judge Hannah Dugan, center, depicted in a court sketch as jury selection in her trial begins in Milwaukee, Wis.

Adela Tesnow/Pool via AP


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Adela Tesnow/Pool via AP

MILWAUKEE — A federal jury found Milwaukee County Circuit Court Judge Hannah Dugan guilty Thursday of obstructing immigration agents as they attempted to arrest an undocumented immigrant defendant last April. 

Eduardo Flores-Ruiz was appearing in Dugan’s court on misdemeanor battery charges. Flores-Ruiz, a Mexican national, was arrested outside the courthouse after a short chase by the immigration agents and has since been deported.

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A grand jury indicted Dugan the following month. She denied any wrongdoing and pleaded not guilty to the federal charges of obstructing a proceeding, a felony, and of concealing an individual to prevent an arrest, a misdemeanor. She was found not guilty of the misdemeanor charge.
 
During the trial, federal agents testified Dugan seemed “angry” when she approached them in the public hallway where they were waiting to arrest Flores-Ruiz after his hearing. They testified that she asked the agents if they had a judicial warrant, sent them to speak with the chief judge, rushed Flores-Ruiz’s case through, and allowed him and his attorney to leave the courtroom through the jury door, which led back to a public hallway.

During the government’s closing argument, Assistant U.S. Attorney Kelly Watzka said Dugan conducted a “round-up” of federal agents and sent them to the chief judge’s office.

Watzka said Dugan then created an “escape route” for Flores-Ruiz when she let him exit a door defendants don’t usually go through. Prosecutors also played courtroom audio of Dugan saying she’d “take the heat” for her actions.

Dugan’s attorneys argued that immigration enforcement policy at the courthouse was in-flux at the time, which led to Dugan’s confusion, and that after Dugan let Flores-Ruiz go through the jury door, he ended up back in the public hallway. They argued this showed she wasn’t concealing him. 

Dugan did not testify during the trial. 

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Dugan attorney Jason Luczak told the jury: “You’re the check on government overreach. Use your power to do justice in this case. You have the power to correct this unjust prosecution. It’s your decision and justice is in your hands.”

Until President Trump’s first term, courthouses were typically off-limits to federal authorities, including immigration agents. He implemented a policy in 2018 giving agents broader authority and has now ramped up immigration enforcement during his second term.



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