Clarissa Glenn’s troubles with the law began on Mother’s Day, 2004, when she was on her way to the Pancake House with her three sons—Ben, Jr., Gerard, and Deon. They left their apartment in the Ida B. Wells Homes, a housing project on the South Side of Chicago, to meet her partner, Ben Baker, outside the building. They found him talking with a police sergeant named Ronald Watts, a notorious figure in the project. Watts oversaw a team of police officers who were supposed to be rooting out the project’s drug trade, but he was in fact running his own “criminal enterprise,” as another officer later put it. Watts extorted money from drug dealers and other residents, and when they didn’t pay him he fabricated drug charges against them. That morning, Ben said, the sergeant had tried to shake him down. Ben told him, “Man, fuck you. Do your motherfucking job,” before walking away.
Clarissa and Ben, who were both in their early thirties, had been together since they were teen-agers. For seven years, they had lived with their sons in the Wells, as the project was known. Ben had grown up there and was used to dealing with hostile, sometimes corrupt officers, but Clarissa, whose father had been a private detective, expected better treatment from the police. In the months after Ben’s confrontation with Watts, whenever she saw a police officer talking to Ben she intervened, marching up to the officer and saying, “What’s going on?” One time, as Clarissa approached, an officer said to Ben, “Here comes your lawyer.”
On the afternoon of March 23, 2005, Clarissa saw from a window in their apartment that several officers had detained Ben, and she followed them to the police station. According to the police report, the officers had caught Ben with packets of heroin in one hand and packets of crack cocaine in his pocket. Prosecutors charged him with drug possession with intent to sell. Ben, who was unemployed and watched the boys after school, had a history of selling drugs, and he was three weeks away from finishing a two-year probation sentence for a drug case. If he was convicted of the new charges, he faced up to sixty years in prison. On April 2nd, he was released from jail pending trial. Clarissa, who worked as an administrator at a home-health-care agency, picked him up.
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Since September 2020, several notable libertarians have established a rapport with political commentator, journalist, and YouTuber Tim Pool. These interactions have resulted in a string of appearances by prominent libertarians on Pool’s daily talk show, Timcast IRL....