Although the Highwaymen are the largest motorcycle club in the city, they are excluded from the Detroit Federation of Motorcycle Clubs as they have a reputation as a criminal organization. The club has undergone a number of large-scale police and FBI investigations, most notably in 1973, 1987 and 2007.
On May 5, 2007, the Federal Bureau of Investigation arrested forty members and associates of the Detroit chapter of the Highwaymen on a number of charges including racketeering, murder for hire, assault, police corruption, cocaine trafficking, vehicle theft, and mortgage and insurance fraud. Twenty-nine illegal firearms, including assault rifles, shotguns and handguns, were also found when FBI agents raided homes and the chapter's clubhouse. The investigation in to the club lasted two years and involved wiretaps and two informants, one of which was eventually murdered.
High-ranking Highwaymen member Randell Lee McDaniel was arrested for running a chop shop in Lansing, Michigan on June 13, 2007. The investigation by the Monroe County Auto Theft Enforcement began in October 2006 and served several search warrants on properties owned by McDaniel. He was charged with conducting a criminal enterprise, operating a chop shop, motor vehicle theft and possessing a controlled substance.
Four police officers and a member of the Highwaymen were indicted on March 12, 2008 by a federal grand jury in Detroit on charges stemming from the 2007 investigation into drug trafficking. Highwaymen member Sean Donovan, who was already incarcerated on stolen property charges, was charged with possession with intent to distribute marijuana and Vicodin. The four police officers were also jailed for corruption.
A Highwaymen-run methamphetamine lab in Eaton Rapids, Michigan was raided by the Tri-County Metro Narcotics Squad and Michigan State Police Emergency Response Team on February 14, 2009. Forty pounds of anhydrous ammonia and a variety of chemicals and equipment that are used to manufacture the drug were found on the scene, as well as methamphetamine itself. One man was arrested at the scene and several others were later apprehended.
Founded: 1954 in Detroit, Michigan, United States
Years active: 1954-present
Territory: Midwestern and Southern United States
Ethnicity: Predominantly White
Criminal activities: Drug trafficking, arms dealing, assault, auto theft, contract killing, chop shop, prostitution, extortion, money laundering, mortgage fraud, insurance fraud, police corruption, and Racketeering
Allies: Sons of Silence
Rivals: Black Pistons and Outlaws