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Second Chalk Time with Regan Benson Delights Fans

by Jim
August 13, 2025
in News
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Long time viewers of Colorado based advocate for the homeless, grandmother and zippy dresser Regan Benson took great delight as she livestreamed twice on Wednesday in which she addressed the state of homelessness in America, interviewed that Randall S. “The Unhinged Attorney” Newman, Esq., and expressed her thoughts on those who oppose her on the internet.

Benson started the day at the Englewood Civic Center, where she admired the chalk graffiti done by a man named Josh in front of the entrance leading to the library. The graffiti read “STOP violating basic human rights Allied Security” and featured text reading “monkey mayor” a caricature depicting Englewood Mayor Othoniel Sierra as a monkey.

The YouTuber explained that Josh was a member of the homeless population of Englewood who had come to the library that morning to discover that he had been trespassed from the library over an incident the day before.

In that incident, Benson explained that Josh was sitting on the floor by a friend in a chair and had spread out his game cards in front of him when he was asked to pick up the cards by Allied Security. Josh objected and was asked to leave the library.

When he returned, strangely armed with a full bag of chalk supplies, on Wednesday, the library was closed due to construction and Josh was apparently summoned YouTuber Benson after being trespassed from the property.

Benson livestreamed from outside the building being generally ineffective, other than a brief moment when she confused a landscaper who was attempting to clean up the graffiti. Benson asked him to stop, and he apparently agreed to let it stay for another three days to appease her objections.

During the protest, Benson was approached by a man named John, who she had previously featured on her channel. Benson had helped John get full-time housing and had helped him furnish his apartment, but he eventually lost the apartment as he could not adjust to life off of the streets.

He joked with her for some time before accepting gifts of water and Gatorade and leaving the area.

Benson’s second stream featured her interview with that Randall S. “The Unhinged Attorney” Newman, Esq. Newman is representing her Helping Hands for Dignity Coalition in a lawsuit against YouTuber BlackHartKnight.

The interview was standard fare for recent interviews with Newman, held late at night in his time zone, with Newman going through the standard series of questions asked by his clients.

New to the by the numbers interview came Benson’s insults directed at those who would use her content without permission. The nearly 50-year-old gray-haired grandmother challenged the ability of her detractors to find mates and engage in sexual activities as they never left their basement domiciles.

Benson invited BlackHartKnight, who was not present in her side chat, to join the panel to discuss the lawsuit after Newman read BlackHartKnight’s comments from a recent video featured on our own ReallyCoolNews YouTube channel.

BlackHartKnight has also acknowledged the lawsuit in a recent video, making it clear that he was never contacted by Newman or Benson before the lawsuit was filed. He also stated that he has no assets and that any judgment against him would result in nothing of value in return.

Newman filed the lawsuit on behalf of Benson earlier this week. BlackHartKnight has yet to be served with the suit.

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Jim

Jim

Jim Finch is a cranky old bastard.

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