ST. LOUIS (AP) — Federal prosecutors are seeking the death penalty for a St. Louis man accused of killing nine people since 2008 during his involvement in a drug trafficking ring.

Anthony Jordan pleaded not guilty to murder and other charges, the St. Louis Post-Dispatch reported Friday.

Prosecutors say Jordan killed three people in 2008, two in 2010, three in 2013 and one man in 2014. Several of the victims were killed while inside vehicles or in drive-by shootings. One woman, a grandmother of eight, died when she was hit by a stray bullet while looking out her apartment window.

Prosecutors say the drug ring brought cocaine from Mexico to St. Louis and that its members had a role in as many as 17 killings. They cite Jordan’s alleged involvement in the ring as one of the “aggravating factors” in their request to seek the death penalty if he is convicted.

Jordan’s attorneys — J. William Lucco, James Henry Moreno and Michael J. Gorla — didn’t immediately reply to Friday emails seeking comment.

Jordan was originally charged in 2015 in connection with three deaths. The indictment was later expanded to include additional crimes as well as nearly three dozen additional people allegedly involved in a violent drug trafficking ring.

Prosecutors contend in court documents that Jordan tried to threaten or harm witnesses and tried to threaten and bribe U.S. Marshals Service or jail workers.

Jose Alfredo Velazquez, who coordinated the shipment of nearly a half-ton of cocaine for the conspiracy, pleaded guilty earlier this month and is awaiting sentencing.

The imposition of the death penalty in federal court is rare. The last federal execution was in 2003 in Texas, according to the Death Penalty Information Center, and only two others have been carried out since the reinstatement of the death penalty in 1988.