Delton Pyles, also known as “Koolie,” a 29-year-old New Haven man, was sentenced to 72 months of imprisonment, followed by five years of supervised release, for his role in a violent New Haven street gang.
According to court documents and statements made in court, Pyles was a member of the Red Side Guerilla Brims (RSGB), a sect of the Bloods street gang based in New Haven. The investigation, known as ‘Operation Red Side,’ revealed that members and associates of the RSGB were engaged in narcotics trafficking and related acts of violence, including murder, attempted murder, assaults and armed robberies.
The investigation, conducted by the Bureau of Alcohol, Tobacco, Firearms and Explosives (ATF), the New Haven Police Department, the Connecticut Department of Correction, the Connecticut State Police, the U.S. Drug Enforcement Administration, the Maine Drug Enforcement Agency and the Hamden Police Department, showed that Pyles was a crack cocaine dealer in the New Haven area, and he supplied other RSGB members with distribution quantities of crack.
On March 19, 2012, Pyles and others were involved in a shootout with a rival gang on South Genesee Street in New Haven. Although more than 20 rounds were fired, no one was injured. The gun that Pyles used during the shooting had been acquired from a straw purchaser in Maine.
Pyles has been detained since his arrest on June 26, 2015. On September 8, 2015, he pleaded guilty to attempted assault with a dangerous weapon in aid of racketeering, brandishing a firearm in furtherance of a crime of violence, and conspiracy to distribute 28 grams or more of crack cocaine.
As a result of this investigation, 21 members and associates of the RSGB were convicted of federal charges in Connecticut and Maine. The investigation has resolved seven murder cases, four attempted murders and four armed robberies that occurred in 2011 and 2012.
Benton, the leader of the RSGB, pleaded guilty to various offenses stemming from this investigation and admitted that he participated in four gang-related murders and one attempted murder. On October 4, 2017, he was sentenced to 480 months of imprisonment.
The investigation has been instrumental in reducing gang violence in the New Haven area, and it serves as a model for future investigations into gang-related crime.
Delton Pyles, Respondent: Delton Pyles, also known as “Koolie,” 29, of New Haven. Charges: Attempted assault with a dangerous weapon in aid of racketeering, brandishing a firearm in furtherance of a crime of violence, and conspiracy to distribute 28 grams or more of crack cocaine. City and state: New Haven, Connecticut. Date: June 26, 2015 (arrest), September 8, 2015 (plea), and November 18, 2015 (sentencing). Sentence: 72 months of imprisonment, followed by five years of supervised release.
Key Facts
- State: Connecticut
- Category: Organized Crime|Violent Crime|Drug Trafficking
- Source: DOJ Press Release â†â€â€
ðŸâ€Â’ Get the grimiest stories delivered weekly. Subscribe free →

