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.

He later started the Minnesota chapter of NORML.

After the Maurers moved to Oregon, Travis Maurer helped spearhead Oregon Ballot Measure 91, which passed in 2014 and legalized recreational marijuana in the state. Leah Maurer was a regular on the cannabis industry speaking circuit.

Quast personally loaned the Maurers $155,000 and sank about $700,000 into a bank account for the company they started together, according to the lawsuit he filed in 2015.

But by September of that year, Quast said he discovered that the marijuana operation wasn’t under construction. He said the Maurers had been using the money to pay personal debts and expenses, and he alleged that Travis Maurer had defamed him to business associates and others in Portland.

Quast filed a lawsuit in January 2016 against the Maurers and an attorney named Dave Kopilak, claiming several types of breach of contract, libel, slander and intentional misrepresentation, and asked for hundreds of thousands of dollars in payment from the Maurers.

The Maurers countersued, saying Quast approved all the expenditures he later objected to and that the growing operation was on its way to completion. They also alleged that his undisclosed struggles with alcohol and prescription drugs caused severe problems for the business, and that he prematurely pulled the plug and tried to undermine them.

They accused him of fraud, breach of fiduciary duty and defamation, and eventually asked the court to award them $5 million for emotional distress and damage to their reputations, arguing that the lawsuit and subsequent publicity had a “devastating” effect.

“The Maurers have alleged that he also conspired with other folks that didn’t really like the Maurers to institute a campaign to blacklist them from the industry,” Andy DeWeese, the Maurers’ attorney, said. “Leah Maurer has been disinvited from events. There are lots of folks in the cannabis industry who won’t work with them.”

The trial in Portland had been set for mid-January, but was delayed for 90 days because of Quast’s bankruptcy filing.

Quast said this week he hopes the dispute can be settled in bankruptcy court rather than in civil court in Oregon.

“I’m a successful businessman. Everything that I would tell somebody not to do, I did,” he said. “I thought I knew something about the industry, and I thought I found someone that could help me. It turned out, my opinion is, I got taken.”