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A courtroom peek at attorney who once defended Freddie Gray and now prosecutes police charged in his death

On May 20, 2013, Freddie Gray stood in a Baltimore courtroom wearing a yellow prison suit, hands handcuffed behind his back. He stood next to his defense attorney — a woman who in two years would be prosecuting six city police officers in his death.

But on that day, Gray was frustrated with his attorney, Janice Bledsoe, over a potential plea deal in his drug case.

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Gray didn't think Bledsoe was his best advocate. At one point during the hearing, Gray even indicated he might have an appeal because of her representation, according to a courtroom video reviewed by The Baltimore Sun.

For her part, Bledsoe appeared exasperated at Gray several times for his unwillingness to agree to the plea deal or speak up in response to questions.

Bledsoe is now the deputy to Baltimore State's Attorney Marilyn J. Mosby, who has charged the officers in Gray's death; all of the officers have pleaded not guilty. The courtroom video offers an unusual look at the day Bledsoe represented Gray at the behest of the public defender's office.

Gray had already spent a year in prison in the case, which involved police finding cocaine and a duffel bag full of razors, glass vials, scales and other drug dealer paraphernalia in his home. He faced a potential 50-year prison sentence if found guilty at trial, but Bledsoe negotiated a plea deal allowing Gray to walk out of the courtroom for time served, along with 18 months of probation and a nine-year suspended sentence.

Gray wasn't going for the plea.

Bledsoe and Judge Michael Reed made sure he was aware of the consequences, the video shows.

"Do you want to plead or not?" Bledsoe asked Gray. He shook his head and said, "No."

"Nope!" Bledsoe told the judge. "Rejected! Can we just please, judge, send this to trial because this really, this is a game that we've been playing."

The judge interrupted her, saying, "It's a game, but it's not a game." He warned Gray that he often saw old men who were once like him 20 years before, as they stood before the same court.

"What they are doing is trying to re-create this day," Reed told Gray. He said the men didn't understand they could get 25 years in prison. He wanted to make sure Gray knew he could spend decades — longer than the life he'd lived thus far — behind bars.

Still, Gray indicated he preferred a trial. But just as they were concluding, Gray agreed to the plea.

Still, tensions persisted when Bledsoe informed him of his right to an appeal based on competent counsel.

"Now you and I have had several disagreements," Bledsoe told Gray, "Is that correct?"

"Yes," he responded.

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"Have you despite disagreements thought that I have represented your interests?"

After a paused, Gray said, "I don't know."

"Are you satisfied with my representation?"

"I don't know," Gray said.

"Would you say that I did something incorrectly?

"Yeah," he said.

It later became clear that Gray believed he should not have been charged, because he wasn't home during the police search.

Bledsoe explained that the prosecution could still win the case. Judge Reed noted that Gray was "not satisfied" with Bledsoe and moved on. And Gray eventually pleaded guilty to violating narcotics laws.

Asked about Bledsoe's past relationship with Gray, Rochelle Ritchie, spokesperson for the prosecutor's office, wrote in an email, "Unfortunately in Baltimore City, many defendants become victims of crime. Lawyers also change roles within the legal profession. Defending an individual one day does not preclude an attorney from fighting for justice for that same individual the next."

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