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Kenosha County Eye

Kenosha Black Lives Matter Activist Is Convicted Of Second DWI And Continues To Defy Judge’s Order

Gregory D. Bennett Jr

***Updated July 28th, 2021 at 11:37 am CST. Since publishing this article, Judge Wagner signed a warrant for Greg Bennett’s arrest.***

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Gregory D. Bennett, Jr is a local Black Lives Matter activist. Bennett attempted to run for Alderman in Kenosha twice- once in 2016 and again in 2018. Apparently, he wasn’t allowed access to the ballot because of several errors with his paperwork, including signatures that were obtained from the wrong district.

On December 4, 2020, Bennett was in court with his far-left attorney, Aileen Henry, who proudly displayed a poster of the late Supreme Court Justice Ruth Bader Ginsburg in plain view of the camera. She was appointed to defend Bennett by the public defender’s office because Bennett reported to make less than $15,950 per year. Bennett was arrested and charged with his second DUI on October 13, 2020. His DUI arrest was after an argument with his wife and a hit-and-run with his neighbor in his Pleasant Prairie mobile home park. He was previously charged in Kenosha with carrying a concealed handgun while bar hopping, but BLM sympathizer DA Michael Graveley (D) dismissed the charge arousing suspicion. He was arrested on March 3, 2013 in Washington State after he blew .154, almost twice the legal limit. Bennett was also carrying a concealed Luger 9mm handgun while he was drunk-driving. Drinking and guns don’t mix.

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December’s Court Hearing

Bennett became visibly upset (video below) when Judge Mary K Wagner (D) ordered him to report to WCS for random drug and breath tests. “WCS for what?!” Bennett exclaimed. “I was an agent!” he later says, although it isn’t clear what type of agent he was. He continues “I was literally a state agent when this happened. So I understand what WCS is, I already lost my job. Now I have to become one of my clients and go to WCS and detain people I worked with….” The Judge stated that “Everyone is the same under the law,” insinuating that he isn’t going to receive special treatment because of his previous employment or status as a BLM activist. Later in the hearing he continues to argue with the Judge saying “I don’t agree with the WCS portion because I don’t have a prior or doing any of this…..” and “I was in an altercation and I had left the scene….” The Judge then interrupts him and then he talked over her stating that he was “wrongfully charged.” Ultimately the Judge did not relent and ordered the WCS program.

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Part of Bennett’s non monetary conditions of bond say that he is *Not to Possess or Consume Alcohol. *Not To Possess or Consume Controlled Substances w/o a Prescription.

On February 2, 2021, February 23, 2021, and April 5, 2021, WCS sent letters to Judge Wagner (D) telling her that he wasn’t participating in the WCS program as ordered. Wanger ignored the letters.

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Plea Hearing

Bennett appeared in court on May 27, 2021 to plead guilty to the second DWI. He was found guilty by the court. The prosecutor on the case, Margaret Drees (D) told the Judge that she received feedback from WCS that Bennett was doing wonderfully. Judge Wagner apparently now noticed the letters from WCS and corrected Drees, saying “No he hasn’t. He’s not doing the treatment.” Drees then acted as though she was looking at the wrong case.

Wagner then told Bennett what Judges aren’t supposed to do – she told him what his sentence would be – the minimum 60 days in jail. She did say that she would adjourn the sentencing to allow him to complete WCS and she would only give him the minimum 30 days in jail. He spoke with his attorney and agreed to complete the program for the shorter jail sentence.

Just today, 7/27/2021 WCS sent another letter to Judge Wagner informing the court that he was in violation of the court order to attend WCS.

Not wanting to be drug tested while on bail for a substance-abuse crime should be suspicious to Judge Wagner and the prosecutor. Judge Wagner’s last day as a judge is this week – she is retiring.

Let’s hope the new judge, Anthony Milisauskas takes in to account his contempt of court orders when he sentences this man.

Bennett at BLM Rally

Bennett is the founder of Kenosha’s “peace in the streets” and ironically always seems to carry a gun while protesting against “gun violence”, to the irking of his democratic friends. According to police records, he does not hold a concealed carry permit so he must carry the gun visibly. Bennett is due to be sentenced on August 13th, 2021 at 9am.

Just last month, the State of Wisconsin filed an unemployment compensation benefit warrant against Bennett for $6,259. An attorney for the Wisconsin Department of Workforce Development declined to tell us why he owes this sum.


  • Kevin Mathewson

    Kevin Mathewson is a disciple of Christ, husband and a father to two wonderful children. Mathewson was born and raised in Lake County, IL and worked as a police & fire dispatcher from 2005 to 2010 in Round Lake Beach, IL. Mathewson moved to Kenosha County in 2006, later being elected to the position of Alderman of the 8th District in 2012 and 2016. Mathewson is a private investigator, security contractor, journalist, and photographer. He enjoys spending time with his family, watching movies, camping and boating. His favorite amendment is the second, followed closely by the first. He loves his country and community.


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4 Responses

  1. From DA Mike Graveley to Prosecutor Margaret Drees, the Kenosha County District Attorney’s Office is rife with BLM sympathizers.
    BLM is a Marxist organizations and those that sympathize and participate in/with this vile organization are terrorists and/or sponsors of terrorism.

  2. He’s out on “Huber” enjoying life. Posting “gotta eat” posts. Our system is a joke. About as funny as the clown wearing his DCU wet weather gear to a riot, screaming thank
    Me for my service

    1. And he was released to be at a wedding today. What a great justice system. Really learning his way. Out all day eating and hanging and now a wedding. I guess you can break the law and do whatever in this town

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