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Defendants arrested in connection with drug distribution ring strike plea deals with prosecutors

Heroin and guns seized Pittsfield (copy)

An assortment of the weapons and heroin seized by police late 2020 in Pittsfield. Several defendants arrested in connection with this investigation have either accepted, or are heading towards plea deals with prosecutors. 

PITTSFIELD — Several defendants arrested in connection with a police investigation into a drug trafficking operation in Pittsfield and Springfield have either struck, or are heading toward plea deals with prosecutors.

The investigation launched summer 2020 when investigators from the Pittsfield Police Department, the Berkshire County Law Enforcement Task Force, state police and the county Sheriff’s Office began probing the operation that was based in Springfield and operated in the Berkshires. 

Pittsfield police investigator Andrew Couture in spring and summer 2020 started investigating alleged drug sales by Raekwan Jackson, of Springfield, from an address at 10 Daniels Ave. in Pittsfield, according to court documents. 

As the investigation continued, a Superior Court judge in September 2020 authorized a wiretap that allowed investigators to intercept electronic communications sent over devices used by Jackson and several co-defendants; Ka'Refi Hillery, of Woonsocket, R.I., Bertram Oram, of Springfield, and Devron Howard, of Adams.

Using information gleaned through the wiretap, investigators received warrants to search addresses they maintained that were tied to Jackson on Liberty and Orange streets in Springfield. According to court documents, in the Liberty Street address police found "a bundle of heroin, a money counter, and loaded firearms which were not securely stored."

In the Orange Street address, where Jackson's girlfriend's mother lived, police found a safe containing several thousand dollars in cash.

However, a judge subsequently ruled that investigators, while seeking the search warrant, had failed to establish probable cause that the Liberty Street address was associated with the drug dealing operation, and agreed with a defense motion to suppress evidence collected during the execution of that warrant. 

On October 20, 2020, investigators saw two suspect vehicles they'd been monitoring in the parking lot behind the Best Western Motel on West Housatonic Street in Pittsfield, according to court documents. 

They had warrants to search a Dodge Journey minivan with Rhode Island plates that Jackson was operating, as well as a search warrant targeting Hillery, who arrived in the parking lot in a gray Volkswagen with two passengers, Oram and Shawn Sanders, of Dorchester. 

Authorities said they seized 13,500 hags of heroin amounting to about 270 grams from a shoebox in the trunk of the Volkswagen. Court papers said Hillery had $1,538 cash. 

Hillery, Jackson, Oram and Sanders were arrested and charged with trafficking more than 200 grams of heroin and conspiracy to violate drug laws. 

A second group of three defendants — who authorities said were tied to the drug dealing operation — was arrested three days later, on Oct. 23, 2020. According to court documents, police acted on information picked up from wiretaps of Kendall Hill and Isaac Howard, both of Pittsfield, and Devron Howard that the group would be making a heroin resupply run that day. 

Authorities tracked a Mazda as it traveled to Springfield and then back to Berkshire County, where police stopped it on Holmes Road in Pittsfield. 

After stopping the vehicle, about 500 bags of suspected heroin "fell from" Howard's waistband, court papers said, that had a street value of about $3,000. Police said a loaded 45-caliber handgun was found in the spare tire wheel well of the Mazda, and that none of the occupants of the vehicle had a license to carry. 

The men were charges with possession of heroin with intent to distribute; possession of a loaded firearm without a license; improper storage of a firearm; possession of a firearm in the commission of a felony; possession of a firearm with prior drug or violent crime convictions; and conspiracy to violate the drug laws of the commonwealth.

Judge Jane Mulqueen on Tuesday approved a plea deal that Hill and his defense lawyer, Colin Keefe, struck with Assistant District Attorney Heather Valentine. Hill pleaded guilty to the drug distribution and conspiracy charges, and the Berkshire District Attorney's Office agreed to drop the firearms charges. Hill, who has been held in pretrial custody for just under a year-and-a-half, received time served and two years probation. 

Valentine said Hill, who is on federal probation, played a minor role in the scheme and there was no evidence that he was involved in "trafficking large quantities of heroin." Saying it was unclear whether he wanted drugs to sell them or for his own personal use, Valentine said Hill was "essentially along for the ride." Keefe said his client was seeking narcotics for personal use. 

Mulqueen said she was "a bit hesitant" to go along with the deal as proposed given Hill's record, which she called "not pretty." But she said Keefe had pleaded his client's case well, and as such, instead of receiving a "significant" term of incarceration, he was able to walk out of the courtroom. 

"I do hope, sir, that you understand what a gift you've been given here today," the judge said. 

Hill, a father of seven, faced up to 10 years in state prison. 

A pair of other defendants also reached plea deals with prosecutors. Sanders and Oram earlier this month pleaded guilty to the lesser offense of possession of heroin with intent to distribute and conspiracy to violate drug laws, according to court documents. Sanders and Oram received time served, followed by one year probation for Sanders and three years probation for Oram. 

A plea offer hearing is scheduled for Devron Howard on June 27, court documents show. Jackson has a plea offer hearing on June 30. 

Isaac Howard failed to appear for a plea offer hearing on June 2, according to court records, leading the court to issue a warrant for his arrest. After he was apprehended by police, Howard's bail was set at $50,000, and has his next hearing on July 1. 

Hillery's case is open and he is due back in court for a status conference on July 25. 

Amanda Burke can be reached at aburke@berkshireeagle.com or 413-496-6296.

Cops and Courts Reporter

Amanda Burke is Cops and Courts Reporter for The Berkshire Eagle. An Ithaca, New York native, she previously worked at The Herald News of Fall River and the Fitchburg Sentinel & Enterprise.

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