Female Massachusetts Attorney Accused of Having Flirty Relationship with Detainee, Smuggling Contraband into Rhode Island Prison

Theresa M. DiJoseph
Theresa M. DiJoseph (left) and a still from the surveillance footage at the Donald W. Wyatt Detention Facility showing her carrying the Marijuana-soaked papers into the facility. Facebook/X

A Massachusetts attorney in a flirtatious relationship with a detainee at the Donald W. Wyatt Detention Facility is facing federal charges of smuggling contraband into the facility, as are the detainee,another detainee, and a detainee's girlfriend.

Theresa M. DiJoseph, 50, an attorney from Woburn who specializes in personal injury cases and represents clients before the Massachusetts Department of Children and Families, is charged with possession with intent to distribute a controlled substance, providing a prohibited object to an inmate, in addition to making a false statement.

The office of US Attorney Zachary Cunha announced the unsealing of the case on Tuesday, shortly after DiJoseph and the detainee's girlfriend's were taken into custody.

DiJoseph Exchanged Flirty Texts, Personal Pictures with Hart, Screenshots of Gambling Bets She Made on His Behalf

Correctional officers thought DiJoseph's behavior was suspicious when she used her credentials as an attorney to visit detainee Shawn D. Hart at the Wyatt facility in Central Falls last July, according to an affidavit. Correctional officers later filed an incident report when DiJoseph was found to be acting suspicious and monitoring the correctional officer's movements.

Hart was in prison awaiting trial on drug and firearm offenses. Over several months, DiJoseph allegedly made flirtatious remarks and other arrangements with Hart, which was recorded on the prison's personal lines.

A review by Wyatt of text messages sent between DiJoseph and Hart on a Wyatt-issued tablet allegedly revealed that DiJoseph had sent Hart personal photos of herself and screenshots showing Cash App or sports-betting transactions that she appeared to have engaged in on Hart's behalf.

DiJoseph Admitted She and Hart Discussed About Having an Intimate Relationship, Confessed to Having Feelings for Him

Donald W. Wyatt Detention Facility
Donald W. Wyatt Detention Facility Facebook

Later, under questioning by the FBI, DiJoseph called Hart a "private client" whom she had been counseling about visitation rights with his children before he was arrested, according to the affidavit. She said she had a fee agreement with Hart, but he has never paid her, according to court documents obtained by The Boston Globe.

DiJoseph told federal agents that she and Hart had discussed having an intimate relationship and she had feelings for him, but that "nothing was ever going to happen between them because she is married and he has a girlfriend," according to the affidavit.

DiJoseph Caught Trying to Smuggle Paperts Soaked in Marijuana

Then, on Dec. 1, DiJoseph attempted to visit Hart with papers regarding capital punishment cases, according to court documents. The correctional officers inspected 10 sheets of paper that appeared discolored, thicker than normal, and to have been wet and dried. An FBI testing lab later confirmed the papers were soaked in synthetic marijuana, according to court documents.

DiJoseph's visiting privileges were revoked. DiJoseph later texted Hart about what to say to the warden: "I'm so mad at you. Why can't you just swoop me away from this madness? Not forever . . . just a weekend . . . what do you think about writing the warden?? Do you think he'll believe me? That I didn't know it was in there?"

She later wrote an email to the warden, claiming she didn't know anything about the drugs on the papers. Federal authorities allege DiJoseph got papers from another detainee's girlfriend. According to the affidavit, Samuel Douglas, a 26-year-old detainee awaiting sentencing at Wyatt, arranged for his girlfriend Hanasa Stedford, 21, to meet DiJoseph outside the prison on Dec. 1 and give her the papers.

Hart, Douglas, and Stedford are charged with conspiracy to possess with intent to distribute a controlled substance, and providing a prohibited object to an inmate. Douglas, 26, is awaiting sentencing in US District Court in New Haven for a charge of racketeering conspiracy. He was also charged in Connecticut with narcotics distribution and firearm possession offenses.

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