They had all gone into cannabis activism after getting busted in SWAT raids.
Randy Quast, who chairs the National Organization for the reform of Marijuana Laws, known as NORML, had built a Minnesota trucking company and sold it for $40 million. Travis and Leah Maurer were prominent in the marijuana movement in Oregon and wanted to start a legal growing operation and dispensary there.
They thought Quast was an "ideal partner" for their venture.
Now they are fighting in Oregon court and Quast has filed for bankruptcy after the operation fizzled. He may owe as much as $5 million to his former business partners, he said in the bankruptcy filing last month.
"I filed bankruptcy as a precautionary thing to protect some of my assets," he said in an interview this week.
The partnership fell apart months after it started, and the Maurers countersued Quast after he sued them three years ago. The $5 million he may owe the Maurers is the largest debt listed in his bankruptcy filing.
Quast, who is 58, moved to Oregon in early 2015 and, shortly after arriving, agreed to invest in a legal marijuana operation with the Maurers. He was the key investor, and they were to build the business using their connections and high profile in the newly legal industry.
The Maurers had previously grown marijuana in St. Louis, where they were hit in a SWAT raid, according to court records. Police found marijuana at Quast's home in Minneapolis while investigating a burglary in 2007, and a task force raided his home the next day.