The motion includes allegations that the Andrews organization dealt in the illegal sale of prescription drugs and that an Andrews associate lied to federal authorities to "protect" Massimino, who allegedly had financed at least one major drug buy for the organization.
Much of the information comes from recorded conversations picked up on a wiretap of Andrews' phone and a bug planted in his Mercedes-Benz earlier this year.
Andrews is on supervised release after serving a 12-year federal sentence for drug dealing. He was released from prison in January 2009, according to prison records.
A law enforcement source said last week the state investigation could be turned over to federal authorities for prosecution and that any charges filed against Massimino would then be added to a racketeering case pending against him and several other top mob figures.
Massimino was jailed in May along with reputed mob boss Joseph "Uncle Joe" Ligambi and 11 others on federal racketeering charges linked to a mob-run gambling and loan-sharking ring.
Andrews, 51, has been described by investigators as a longtime South Philadelphia mob associate. He was sentenced to 12 years in federal prison in 1998 after being convicted of dealing in large quantities of methamphetamine.
Andrews' apartment on Passyunk Avenue was one of several locations raided in April by investigators with the state Attorney General's Office. Search warrants indicated the raids were part of an investigation into loan-sharking and the illegal sale of prescription drugs, including oxycodone.
More details about that investigation surfaced at a bail-revocation hearing in U.S. District Court on Wednesday for Robert Cohen, who authorities say worked for Andrews in the drug operation and served as his driver.