The Cannabis Operator Prosecutors Got Like Al Capone
In this first-person commentary, Ryan Richmond argues that after marijuana charges failed, federal authorities turned to tax law—specifically Section 280E—to win the conviction that sent him to prison.
Editor’s note: This essay is a first-person opinion piece by Ryan Richmond. It reflects the author’s recollections, views, and legal arguments about his prosecution and the use of Section 280E against cannabis operators. High Times has edited the piece for clarity, length, and context.
My name is Ryan Richmond: former medical marijuana dispensary owner and now a convicted felon. I served one year in federal prison on a two-year sentence. My probation will soon be over. Here’s the part that surprises people: I didn’t go to prison for selling weed. I went because the government couldn’t make that narrative stick, so it did what it often does in that situation—it reached for another weapon and won.
As you might imagine, I had a lot of time to think in Morgantown Federal Prison in West Virginia—time to read, time to write, to research, and to reflect—and I took full advantage of it.
The Wild West of Michigan Medical Marijuana
My story began in 2009 and ended in, well, I’m sure it never ends. After the 2008 Michigan medical marijuana initiative’s 63% landslide victory, a few partners and I started Clinical Relief in Ferndale. We became the first licensed medical marijuana dispensary in the state. That’s not bragging; it’s for context. Being early meant there was no real precedent and very little guidance. This was the wild west, and we were pioneers.
Fast forward. Just before saying my goodbyes to my wife and children, as I was preparing for prison, my appellate lawyer, Stu, told me two things:
1) What happened to me was rare—one of a kind, actually. Cannabis battles around IRS Code 280E usually play out in civil court, not criminal court. He told me he couldn’t find another case where Code 280E had been used this way in a criminal prosecution and that, as far as he could tell at the time, I might be the only American sent to federal prison over it, and
2) He told me the feds got me the same way they got Al Capone: through tax charges. I laughed at the Al Capone comparison; just one of those reactions you might have when you’re about to be caged.
Stu had represented me before—back when Michigan’s medical marijuana experiment was just born, when “licensed” didn’t mean what it means now, and when being early didn’t make you brave; it made you vulnerable. He’d been with me in state fights, including a landmark case that went all the way up to the Michigan Supreme Court. None of the bullshit ever stuck—cases dismissed, or no charges ever filed at all. But the result was always the same: we’ll just keep your money. Thank you. To me, it was always about the money.
Raids, Attrition, and Wearing You Down
I’m speaking out for one reason: to put a clear record on paper. What happened to me wasn’t just about cannabis—it was about how power shifts when one tactic stops working.
For four years, my businesses and home were raided an average of every 26 days. Multiple arrests. Multiple prosecutions. None of them stuck. Raids are loud. Guns. Vests. Intimidation dressed up as procedure. It wears you down—financially and psychologically.
When it came to raids, they often seemed to happen on Friday nights. I came to believe that timing was the sweet spot: our dispensaries would be flush with cash and have higher weekend inventory, and staff could end up spending the weekend in jail.
By the time the government came after me for tax evasion in a case tied to IRS Code 280E, I was drained. Money seized. Documents gone. Legal bills stacked. When the drug charges didn’t land, the tax code did.
That’s the part people don’t see. The war doesn’t always end in a dramatic conviction. Sometimes it just changes tools.
One of the system’s major tools is to shift the legal ground; that is, change the laws or the rules. What a casual reader might not understand is that the cannabis industry didn’t become “legal” in a straight line. It lurched. It retreated. It hid. It marched forward. It contradicted itself. We were constantly second-guessing—because the rules were unstable and enforcement was… selective, to put it politely. Before the ballot vote, some of the same people who claimed we would have a dispensary on every corner later claimed that the law never allowed dispensaries. To me, that was fearmongering—the kind a dying system does best.
Enter IRS Code 280E
To understand what I mean by shifting legal ground, the case I was convicted in centered on IRS Code 280E. In my view, 280E became a powerful tool against the state-legal marijuana industry as reform spread across the country. So when the raids and arrests never resulted in a single conviction for me, enter the tax man.
For decades, 280E had primarily been litigated in civil tax court. When 280E was enacted in the 1980s, it was intended to prevent drug traffickers from deducting expenses. Simple rule: if you’re trafficking in a Schedule I or II substance, you don’t get the normal deductions every other business in America has—rent, payroll, security, marketing, insurance, the boring costs that keep the lights on.
Cannabis is still treated as Schedule I under federal law, so even if you’re legal under your state law, federal 280E treats you like a drug kingpin; it doesn’t care who is legally sanctioned by whatever state. In my view, the government used to take your money through asset forfeiture. Now it takes it with IRS Code 280E. They’ve upgraded their tools.
280E wasn’t just dusted off; it was pulled down, polished to a shine, and put to work on a new class of people: the marijuana industry—all to keep the old system alive for another day. Of course, this is how they got me. The system used its upgraded weapon: 280E. The IRS now looks at your books and says, in effect: You can’t deduct any of that. I was criminally convicted and hit with roughly $1,000,000 in taxes and about $1,800,000 in penalties—after already personally losing something like $1,000,000.
The Constitutional Fight
My case went through a jury trial, the appeals court, and the full federal grinder—and the question that remains unanswered, at least for me, is this: can IRS Code 280E, a civil tax rule, become unconstitutionally punitive when paired with a criminal indictment? I took that question all the way to the U.S. Supreme Court, and the Court declined to hear it. My appeal argued that denying deductions under 280E was unconstitutional. The Eighth Amendment to the United States Constitution prohibits excessive bail, excessive fines, and cruel and unusual punishments. This amendment was adopted on December 15, 1791, along with the rest of the United States Bill of Rights.
So, I was convicted for tax evasion. Here’s the part that is the cruelest: besides the basic business expenses that I could not deduct, I also couldn’t deduct the money I paid for lawyers, the money seized during the raids, or the money seized from my accounts. In addition, I was unable to access certain seized records during my defense.
In December 2025, President Donald Trump signed an executive order directing the Attorney General to take steps to expedite the process of moving marijuana from Schedule I to Schedule III under the Controlled Substances Act. The order did not itself reschedule cannabis, but it accelerated the ongoing rulemaking process that began after the Department of Health and Human Services recommended rescheduling in 2023. If finalized, a move to Schedule III would eliminate the 280E tax penalty for state-legal cannabis businesses.
280E is a big deal, certainly one of the biggest roadblocks facing the industry today. In my view, 280E is punitive, used to inflict harm and maintain the “order” that is the status quo. This is the part that makes 280E so powerful and so politically useful. It doesn’t require the government to win an argument about the pros or cons of cannabis. It doesn’t have to be a debate between medicine and vice. It doesn’t need a public campaign. It just needs to look at your books and say, “You can’t deduct that, or that, or any of that.”
They could never convict Al Capone for bootlegging or even murder—he went down because the taxman was cleaner, quieter, and easier to sell to a jury of his peers. Likewise for me. Stu was right.
What I have that Al didn’t is what I believe is a solid constitutional argument that the system won’t address: that 280E can become punitive in ways that implicate “excessive bail, excessive fines, or cruel and unusual punishments.” Understand: to me, one of the practical effects of 280E is attrition—taking your money so you can’t continue with the rising court costs. They want to make sure you can’t afford to keep proving them wrong.
From Doors Kicked In to White-Collar Enforcement
A usual question I’m asked is what’s different between now and the early medical cannabis days. The big thing is that today, the cannabis industry grapples with the brutal Code 280E. In my day, doors got kicked in, and children got scared. We are now moving from blue-collar enforcement/control to white-collar enforcement/control.
I would expect that 280E will encourage more black-market transactions, resulting in less tax revenue. Maybe that’s what the system wants, as it is job security. Simply put, job security versus society. While in prison, I found that the biggest lesson most people learned the hard way, whether related to cannabis or not, is this: things aren’t fair, and if you stick your neck out, somebody’s always ready to chop it off.
I hope the points I wanted to stress came through in this article: 1) If you have an encounter with the legal system, record it, date it. If you are able to share your experience, please do. Who knows, maybe in the future, some PhD criminal justice student could use your record, or 1,000 records, and 2) educate people that the system never stops. This is scary: a system that doesn’t allow societies to advance, instead believing that destroying lives will win their war.
In my reflections, I keep coming back to the same uncomfortable truth: cannabis legalization didn’t end the war. It rebranded it. Our culture has shifted, but the system won’t. Some day it will need to shift again—because the machine never stops, it just changes uniforms and letterhead.
People love to talk about this era as if it were inevitable—like legalization was a smooth march forward led by wise policymakers. It wasn’t. It was messy. It was bloody. It was human. It was expensive.
And for some of us, it was a cage.
This essay is a first-person commentary by an external contributor. It reflects the author’s views, recollections, and legal arguments.
