Pearson said her life turned around at the age of eighteen, when Arnold Loney, a local drug dealer who looked out for her and sent her money in prison, was shot and killed. He had coined her nickname “Snoop”, because she reminded him of Charlie Brown’s beagle Snoopy in the comic strip Peanuts. While in prison, Pearson earned her GED. She was released in 2000, and landed a local job fabricating car bumpers, but was fired after two weeks when her employer learned she had a prison record.

On March 10, 2011, Pearson and sixty others were arrested and charged with drug offenses. The arrest was made during a predawn raid at her home in Baltimore, following a five-month DEA operation. At the first hearing after Pearson’s arrest, Judge John Addison Howard denied her bail due to Pearson’s acting ability, stating: “Well, you can change your appearance, I’ve seen the episodes of The Wire in which you appear. You look very different than you do here today, and I’m not talking about the jumpsuit, I’m talking about your general appearance.” After a month in jail, Pearson was offered bail of $50,000 on April 8, 2011. In August 2011, she pleaded guilty to the charges the day before her trial was to begin. She was sentenced to a suspended seven-year prison term, with credit for time served, and given three years of supervised probation.