A federal judge today sentenced Gary Webster to eight months in prison after he was monitored five times selling cocaine and fentanyl on Codman Hill Avenue in Dorchester in 2016, while he was working as director of constituent services for at-large City Councilor Michelle Wu, who at the time was city-council president, the US Attorney's office reports.

By the time of his arrest in 2018, as part of a 29-person federal and state roundup, Webster had moved over to the BPDA, where he worked as a project manager - his arrest forced the agency to postpone a hearing that night on a proposed Allston residential building he had been shepherding through the regulatory process. Webster is the second BPDA manager sentenced to federal prison this year.

Prosecutors say Webster was caught in surveillance selling a total of 300 grams - two-thirds of a pound - of cocaine and 49 grams of fentanyl to a buyer who turned out to have been working with the feds, on five occasions in September and October of 2016.

Webster pleaded guilty last November. Prosecutors had sought 30 months, arguing that even with a guilty plea, Webster deserved at least that much time in prison both because of the harmful effects cocaine and fentanyl have had in eastern Massachusetts and because:

"His criminal conduct was not a single isolated incident, but instead a concentrated effort to essentially undermine the same community he was tasked with helping through his government employment. On the one hand, he was selling dangerous drugs in the street for financial gain, while furthering a career in politics with the other. ...

"The defendant in this case is a prominent member of the community, who nonetheless engaged in dangerous and harmful criminal conduct. This 30 month sentence, if imposed by the Court, would be the defendant’s first prison sentence. Given the defendant's education, work history and supportive family, the government anticipates that the 30 month sentence would be sufficient to deter the defendant from returning to drug distribution."

Webster's attorney argued for a more lenient sentence for the Boston Latin School and UMass Amherst graduate, who had worked for the state Department of Transportation and the Boston Zoning Board of Appeal before Wu hired him, and who is a father of two.

"Gary has worked at his father’s family catering-restaurant business in Dorchester since his arrest in this case. He is an important source of income and financial support to his family. Gary has had a significant period of time to reflect on his criminal behavior and the wrongfulness of his conduct. He understands full well the damage narcotics has had on society and recognizes that his participation in this offense was wrong, is a bad thing and that he should be punished."

The defense sentencing recommendation urged US District Court Judge Allison Burroughs to be lenient because Webster played only a "minor role" in the sales, that he was, in fact, just a go-between for the real drug man, Jonathan Andrade - who was sentenced in 2018 to ten years in prison on charges of selling even more drugs than Webster, as well as unlawful monetary transactions and being a felon in possession of a firearm. Andrade, Webster and the unnamed buyer, the memo continues, are all related and have known each other for years.

"Gary was approached at a funeral for his aunt by the cooperating witness in August of 2016. The defendant and cooperating witness are related and Gary has known him his entire life. The cooperating witness asked Gary if he (Gary) could speak with Jonathon Andrade about selling him drugs. The cooperating witness knew from the inception of the investigation that Andrade was the source of the drugs as he knew Andrade for many years because they were also related. For the ensuing cocaine transactions Gary acted as a middleman between the supplier and buyer. For the final purchase (fentanyl) Gary was present and took possession of the buy money in the basement of the Webster family home in Dorchester where Andrade, the cooperating witness and Gary were present. Webster was paid a stipend of $500 for each of the drug purchases, and did not otherwise share in the profits of the drug sales. For each of the cocaine transactions Andrade delivered the cocaine to Gary, after Gary learned the requested drug amount from the buyer. Andrade brought the fentanyl to the final transaction in the basement of the Webster home in Dorchester. "