The Highwaymen Motorcycle Club in Detroit, the state of Michigan’s biggest and only traditional homegrown biker gang, took a major hit 30 years ago with a 1987 federal racketeering and drug indictment which took down close to two dozen club members and administrators. It was the first significant dent made by law enforcement in the Great Lakes region in their tireless fight against the unruly Highwaymen, founded in Southwest Detroit in 1954 by the area’s original biker boss, Elburn (Big Max) Barnes and known to be on the wild side, even for “One Percenters.”

The ’87 indictment and subsequent incarcerations of key club rank-and-file in Southeast Michigan might have floored the chopper chiefs of Detroit, but it proved far from a knockout blow. The Motown Highwaymen contingent was back up and running at a high level within a few short years.

The club has been back in the headlines lately with the recent revelations that New Millennium Highwaymen leaders could have grounds to appeal lengthy prison sentences they’re in the middle of serving based on the uncovering of a possible mole in their defense camp at trial in 2010. Two of those currently behind bars hoping to leverage the new information into a new trial for themselves, Highwaymen Godfather Leonard (Big Daddy) Moore and the club’s former national president Joseph (Little Joe) Whiting, were nailed as part of the 1987 bust too.

The feds No. 1 target in the Highwaymen in the Reagan Era was Jason (Reaper) Gray, Big Max Barnes’ protégé and successor as national president upon Barnes sudden death from a massive heart attack in the summer of 1980 when he was just 48. Barnes’ funeral was an elaborate affair, including hundreds of bearded, leather-clad biker brethren gathering to pay their final respects and featuring a dramatic 21-gun salute preceding Barnes being buried in a sterling-silver plated coffin.

Under Gray’s reign, the Highwaymen dipped deeper into narcotics and away from the extensive prostitution network the club had used to keep its coffers flush with money in its first quarter century of existence. As part of a DEA and ATF raid of the Highwaymen’s “mother ship” headquarters in Southwest Detroit in August 1987 authorities confiscated 15 pounds of cocaine, one pound of PCP, $165,000 in cash, an estimated $40,000 in stolen jewelry and 120 weapons, most of them automatic guns in varying degrees of size and caliber.

The indictment finally landed on October 15, 1987, charging 22 Highwaymen and Highwaymen associates with 15 racketeering counts, including drug trafficking, robbery, kidnapping, assault, attempted homicide, arson and witness intimidation. The 72-year old Gray, who authorized a murder contract on an area police officer and a bombing campaign aimed at a rival criminal faction, was convicted and did four years in prison. He was released from federal lockup in March of 1991.

The Highwaymen maintain chapters in Michigan, Indiana, Florida, Kentucky, Tennessee, Alabama, New York and New Jersey. There are eight chapters in the state of Michigan alone – Downtown Detroit (SW), Eastside Detroit, Westside Detroit, Northwest Detroit, Downriver, Ann Arbor, Lansing and Monroe. The national president for the club traditionally resides out of Highwaymen Country Ground Zero, the Southwest Detroit clubhouse on Michigan Avenue.

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