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Is Regan Benson the World’s Oldest Mean Girl?

by Jim
July 26, 2025
in News
Reading Time: 3 mins read
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Days after announcing that she was no longer focusing on homeless outreach, Regan Benson livestreamed on Friday asking for donations to her organization and mocking the response to a lawsuit she filed against the city of Englewood, Colorado.

Benson started the stream by introducing a woman named Stephanie, who had previously appeared on the stream last month as Denver police attempted to confiscate her recreational vehicle after deeming it abandoned on the streets of Denver’s District 3.

The YouTuber filmed the situation while another homeless advocate negotiated an actual positive end to that situation as Stephanie was allowed to leave the area with her vehicle.

Benson shared news that the police tried again this week as the vehicle had expired plates and tags. According to Benson’s account, the Denver police circled the vehicle with five police cars, and a tow truck driver was in the process of hooking the vehicle up to his tow truck when police knocked on the door of the vehicle and evicted Stephanie this week.

Stephanie did not take the situation lightly, as she followed procedure and asked for a review by Denver’s parking magistrate. The magistrate reviewed the seizure and found that Denver’s District 3 police acted illegally in seizing the vehicle and ordered it immediately returned to Stephanie.

Benson drove Stephie to get new tags for the vehicle and updated plates were apparently ordered at the same time. Because funds from Benson’s 501(c)(3) organization, the Helping Hands for Dignity coalition, were used, Benson asked for her fans to make donations to her Venmo or CashApp accounts.

The actions came just days after Benson had said she was taking a break from homeless outreach and was unsure of the future of her organization.

As Benson sat with Stephanie at the city of Denver’s impound yard awaiting service, Benson began to discuss her on-going civil lawsuit against long-time nemesis, the City of Englewood, Colorado.

Benson took on the expression and tone of a character from the movie “Mean Girls’ as she began to read from the counterclaim made by the defense. She took time to mock defamation claims made in the counterclaim, including her various statements insulting all parties in her lawsuit and indicating on one of her YouTube videos that two librarians were sexually pleasuring members of the Englewood Police Department.

The defendants have requested a jury trial for their counterclaims and are seeking economic, punitive and compensatory damage plus attorney’s fees.

Benson called the defense’s motion to dismiss her lawsuit a “joke” and indicated that it had no merit and would be easily dismantled by her attorney. The counterclaim itself takes issue with Benson’s allegations and states that police had probable cause to arrest Benson for an incident where she was alleged to have livestreamed herself relentlessly harassing an Allied Security Guard at the Englewood public library.

All other actions taken against Benson were justified as they were simply the enforcement of existing city and municipal codes and not a vast conspiracy to impede Benson’s first amendment rights.

The motion to dismiss also takes issue with Benson accusing Englewood Mayor of not allowing her to speak at a public meeting held on January 5, 2025, when no such meeting took place.

Benson dismissed the motion to dismiss as pathetic but did not discuss the claims with her 26 live viewers.

Eventually, Stephanie received clearance to retrieve her vehicle and Benson was in the process of driving her to another impound yard to retrieve it when the livestream abruptly ended.

Benson vs. Englewood – 24 – Counterclaim
Benson vs. Englewood – 25 – Motion to Dismiss

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Jim

Jim

Jim Finch is an accomplished journalist and writer of things. He currently resides in Cogan Station, PA, where he is continuing his love affair with the Seattle Mariners and Seattle Seahawks. He also likes to confuse people with his entries in biographical fields.

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