Derrick Bailey, Drug Trafficking, Illinois 2025

Springfield Man Sentenced to 180 Months for Drug Trafficking

A Springfield man, Derrick Bailey, 44, was sentenced to 180 months in prison for his role in a widespread drug conspiracy involving a Springfield street gang, Boss Playas, lasting from approximately May 2020 through November 2020.

According to court documents, Bailey was held accountable for trafficking over 10 kilograms of cocaine as a member of the conspiracy. The group of conspirators were responsible for distributing large amounts of controlled substances in the Springfield area, which had a negative effect on the community.

Co-defendants in the case have received the following sentences of imprisonment: Denziel Witherspoon, 240 months; James Cooper, 180 months; Christopher Wallace 120 months; Isadore Montgomery, 120 months; Rashaud Brown, 84 months; Paul Davis, 40 months; and Taylor Cockrell, 36 months.

Additional defendants Dorothy Jackson, Shelton Witherspoon, Lavar Maney, Haley Riley, and Haylee Vaughn have pleaded guilty and are awaiting sentencing.

Bailey was indicted on December 15, 2020, and pleaded guilty on September 18, 2024. He has remained in the custody of the United States Marshal since his arrest on December 1, 2020.

The statutory penalties for the most serious charge of conviction include up to life in prison, up to a $20,000,000 fine, and up to a life term of supervised release.

This case was investigated by the Drug Enforcement Administration; Federal Bureau of Investigation, Springfield Field Office; Illinois State Police; and Springfield Police Department. Assistant U.S. Attorney Matthew Z. Weir represented the government in the prosecution.

The case against Bailey was part of an investigation of the Springfield-based Boss Playas street gang and was part of an Organized Crime Drug Enforcement Task Forces (OCDETF) investigation.

OCDETF identifies, disrupts, and dismantles the highest-level drug traffickers, money launderers, gangs, and transnational criminal organizations that threaten the United States by using a prosecutor-led, intelligence-driven, multi-agency approach that leverages the strengths of federal, state, and local law enforcement agencies against criminal networks.