15 Years Lawyering in Oregon Cannabis, and Beyond

Last month, we hosted a webinar on federal cannabis law and policy in 2026. While things are not where we’d like them to be, it’s amazing to consider everything that has happened over the years. From a lawyering perspective, it’s almost unbelievable.

I have worked as a business lawyer in the cannabis industry for over 15 years. It’s been a long, strange trip as the poet said. And I’m grateful for it. Below is a long-form piece on how it all went down.

2011

I was a second-year lawyer at a business firm downtown when a medical marijuana dispensary owner came through our office. (Back then, nobody said “cannabis.”) His shop was here in Portland, with a grow in the back, and the owner had been passed along by two other law firms that felt uncomfortable advising him. This gentleman had received a bankruptcy trustee’s notice on his door, advising that his landlord was in a Chapter 7 (I think). He desperately wanted to stay in the building. Maybe even buy it, somehow.

We looked at the lawyer ethics rules, called the state bar association, read the Ogden memo, etc., and it was unclear whether we could assist the client—even regarding compliance with state and local laws. It was unclear whether our malpractice insurance extended coverage. It was unclear whether our bank would take the deposits. It was unclear if his business even complied with Oregon law to begin with. Everything was unclear; no one would opine. The first Cole memo issued that summer, making things even more confusing. But, the answers were not clearly “no” and my boss invited me to try. I had no problem with any of it.

I ended up helping the client reach a deal to pay cash rent to the Trustee—which would never happen at this point: the payment part is wild; the cash protocol, outrageous—and then I started helping him with business agreements and everything else. Back then, there were virtually no lawyers working on non-criminal cannabis issues. He started sending me industry referrals, one after another. It was a crazy time—the work was less sophisticated but also more challenging in some respects than much of what we do today.

Seems like all of those people are gone now.

2012

Oregon was not licensing medical marijuana dispensaries, but people were boldly opening collective-style storefronts, like the guy I just mentioned, ostensibly under the state’s decades-old medical marijuana statute. That law was not designed for commerce, at all. The policy idea was to simply to confer an affirmative defense to “patients” and “caregivers” from prosecution under state law for cannabis possession and use. That’s as far as it went.

A lot of the businesses I dealt with in those days had self-organized as non-profits and collectives and such, as borrowed from the California model. I couldn’t find accountants for them, or anything really. It was such a mess.

That fall, Oregon’s Measure 80 narrowly lost at the polls, 47% to 53%, while Colorado and Washington passed legalization measures. Measure 80 would have legalized cannabis for adult use statewide in Oregon, established a licensing and taxation system, etc.—which ultimately happened a few years later under Measure 91. Elsewhere, industry pioneers like California’s Harborside dispensary (who would later become a client; then go public; then fail) were going at it with the feds. In those days, everything was a rock fight.

2013

The Oregon legislature passed a law called HB 3460 that August, directing the Oregon Health Authority (OHA) to write rules and launch a registry system for medical marijuana operators. This was a big deal! Clients seemed nervous: there was no industry lobby to speak of, and everything coming from Salem seemed reactive.

The second Cole Memo also issued that summer, in response to the pending Washington and Colorado adult use programs. It felt like things were changing pretty fast. My boutique business law firm “merged” with a mid-sized law firm downtown that catered to financial institutions and did not like cannabis. I continued to quietly do the work. A lot of that work was unsupervised; somehow it all worked out.

2014

OHA issued its rules, which were skeletal, unenforced and ass-backwards on certain things. There were no cannabis testing requirements; no grandfathering protections for current storefront operators; a rule that people who had been convicted for “manufacture or delivery of [cannabis]” couldn’t be “responsible for” a cannabis store (?!); and I can’t even remember what else. But I recall clients coming to us with so many questions and problems which were essentially unanswerable, because the framework wasn’t there. That November, Measure 91 passed, legalizing cannabis for adult use in Oregon. Finally.

On the federal side, the Department of the Treasury issued the FinCen Memo on “BSA Expectations Regarding Marijuana-Related Businesses.” This was accompanied by another DOJ memo titled Guidance Regarding Marijuana Related Financial Crimes, and a DOJ memo on “Marijuana Issues in Indian Country.” The latter two directives were rescinded four years later by Attorney General Jeff Sessions, but the FinCen Memo is somehow still in effect. More than a decade later, I would find myself advising banks, credit unions and even the federal government on that cumbersome guidance.

2015

The Oregon legislature started messing with Measure 91 almost immediately in drastic ways (e.g. tax structure, residency requirement). Some of my clients started to ramp up to transition into the OLCC program, but many sat back and waited. People were getting bigger and bolder on the medical side. We began to see a proliferation of medical marijuana processors and “wholesalers” around this time, although none of this was contemplated in the rules. Lots of crazy stories.

The Oregon State Supreme Court amended the attorney ethics rules in February, to expressly allow us lawyers to work with marijuana business “regarding Oregon’s marijuana-related laws.” Most lawyers remained on the sidelines, though. I left my old firm in June, and started the Portland office of what would become Harris Sliwoski LLP. A lot of people seemed to think that was a crazy move, but it was really fun. I started writing intensively here on the blog and I wrote the first of 100 columns for the Portland Mercury. I stopped doing litigation entirely.

Adult use and possession became legal on July 1, which was awkward in the sense that OLCC had not yet licensed stores. The state eventually capitulated and allowed early sales through existing medical dispensaries on October 1. The whole system was still vexing from a contracts perspective—the cannabis being bought and sold all came in through the OHA supply chain, which meant it was theoretically the property of medical marijuana patients, at least to start.

I worked with another lawyer in my firm on one of the OLCC rules advisory committees, and the first batch of the OLCC program rules dropped in October of 2015. The Commission made a valiant effort there, but business acumen was lacking. The “financial interest” and “residency” rules were terribly confusing, and basic commercial concepts were not addressed, from convertible notes to security interests. The City of Portland was even worse.

Folks started lining up to submit OLCC applications on January 1, 2016. I recall organizing and incorporating a dizzying number of little companies in the months leading up to that date. Back then, a common setup was someone with property, a guy who knew how to grow cannabis (always a guy), and maybe an investor with $200,000 or so. Really simple stuff. I testified before various cities and counties with respect to cannabis-related zoning ordinance proposals. Some of those hearings were well-run and respectful; a few went off the rails.

2016

We muddled through licensing and the system began to launch. I recall one of our producer (grow) clients being told they were the “third licensee in the state.” The legislature began to fiddle with the system further, including through repeal of the residency requirement (HB 4014). It’s hard to overstate how important this was: no other jurisdiction in the world had a cannabis program where non-residents could be owners. Calls started coming in from everywhere and people could not seem to get their minds around it. But the rules were clear: you could be from Oregon or California or Israel or Spain. You could be from Mars.

We answered a lot of questions about federal law enforcement back then, which hardly happens anymore. The fear factor ticked up substantially again in November, when Donald Trump was elected President. That same election night, California, Nevada, Maine and Massachusetts all went recreational (and Arkansas, Florida and North Dakota all adopted medical programs), making the state/federal dynamic more dissonant than ever. Locally, more and more OHA program participants made their way into the OLCC system, while others stayed put or went off the grid altogether.

OHA finally got its act together and started licensing medical marijuana processors, even though the medical program was clearly on the way out. The Oregon Department of Agriculture (ODA) passed a key law to propel the stalled state hemp program, and we had a few clients start in on that. They had logistical problems you wouldn’t believe, including finding seeds.

2017

Jeff Sessions was confirmed as Attorney General to kick off the year. People will say that didn’t scare anyone, but I’m here to tell you that investment slowed a bit. By mid-year, though, the OLCC program began to hit its stride. Things felt mostly “built” for the first time, even if a testing lab bottleneck persisted, with other program kinks.

By December 2017, there were almost 900 licensed farms in Oregon, and the M&A market started to gain steam. There was a lot of press at this point about oversupply, unlicensed cannabis and diversion. The faddish and wasteful RICO lawsuits were in full swing. Here at the law firm, we were also fielding fewer calls from “medical marijuana growers,” although it was known that folks were still stacking cards and everything else. That said, all of those 90-plant medical grows were going the way of the buffalo.

Elsewhere, many of the newer businesses were already failing and folks started suing one another in earnest. Reporters still called whenever lawsuits were filed. I recall posting ads for litigators, and wondering if OLCC licensees would figure out how to make money in the regulated market. I also sat for a series of lunches with lawyers in mid-sized and large law firms who were poking around the Oregon space. Finally, I took a few calls from the FBI and U.S. Attorneys on client-related investigations. Not great.

On the hemp side, we saw more and more clients pursuing CBD sales, which were coming into vogue notwithstanding confusion about the 2014 Farm Bill and everything else. Under Oregon’s pilot program people got crops in the ground, however. And with federal discussion looming, it felt like hemp was finally on the way.

Elsewhere, I became an owner at the law firm on January 1, and we opened offices in San Francisco and Los Angeles, which were highly productive for a time. That summer, I was cynically sued in circuit court for “civil conspiracy” by a poorly supervised colleague at a large law firm. The allegations were based on advice he assumed I’d given to a cannabis client. That claim went nowhere.

I began teaching a Cannabis Law & Policy course in the fall, which continued over a five-year period. We had Earl Blumenauer come speak and things like that. In 2017, it was the second or third such class on offer nationwide. Class was sold out and then some.

2018

Jeff Sessions kicked off the year by rescinding the Cole Memo, which got people jittery once again. The local “oversupply” conversation was coming to a head, such that Oregon U.S. Attorney Billy Williams felt the need to author a memo of his own. Immediately thereafter, the OLCC “paused” its intake of marijuana license applications—possibly as a result of the memo, but also because the Commission was just so far behind.

The Canadian invasion was also in full swing at this point. Many of our local clients were rolling up on the Canadian Stock Exchange through reverse mergers, or wondering how to do this, or talking with someone about doing it. Other clients despised the whole thing. And still other clients WERE the Canadians. Foreign dollars were also pouring into other western states by this point, mostly California and Nevada.

I cannot tell you how many mergers, reverse mergers, option agreements, stock sale agreements, asset purchase agreements, convertible debt agreements, etc. etc. we papered around this time—even as prices tanked. It was incredibly dynamic and incredibly fast. Around this period, we also were hired by a series of large-cap, bellwether U.S. companies trying to understand the CBD market and what could be done there. Lots of opinion work, with corporate campus visits. We did a series of celebrity collabs, too; a few of those are still going strong.

Outside of Oregon, I doubt there was ever a bigger year for cannabis than 2018. California commenced its adult use marketplace, the U.S. legalized hemp through the 2018 Farm Bill and Michigan became the first midwestern state to go full rec. Internationally, Canada legalized marijuana federally, Mexico announced its plan to do the same, and the U.N. announced it would revisit cannabis scheduling. Oh, and Jeff Sessions was sent on down the road. It was awesome.

2019

Hemp was probably the biggest story locally in 2019. Nearly 2,000 growers registered to plant over 63,000 acres, a nearly 6x acreage increase from the year prior. Then the problems came. Much of the hemp went unharvested due to bad weather and inexperience. Prices also fell through the floor along the supply chain, from seeds to finished products. Our office handled more litigation on the hemp side than on the THC side. And people started to use ODA licenses as cover for diversion, rather than persisting in the OHA (medical marijuana) system.

Federally, USDA seemed to slow walk the rules, and FDA was as useless as ever. The ODA’s adoption of a “total THC” testing standard was also hard for operators. Nationwide, the CBD craze was in full swing. Some of the country’s largest grocers, distributors and CPG companies hired us and flew us around, after buyers and marketing departments got ahead of themselves. The high point was being flown to D.C. and advising the National Credit Union Administration on guidance it issued for hemp banking.

On the THC side, the Oregon legislature finally passed a law to curtail the award of cannabis production licenses, bowing to pressure from all sides. It was too late to have much impact, although the effort did create a strong secondary market for producer license transfers (which we continue to trade in today). The legislature passed another forward-looking law to allow cannabis exports; the idea here was to set up local growers for the end of prohibition. Finally, vaping came into the regulatory crosshairs, resulting in more litigation.

2019 was the first year that the OLCC market seemed to really settle out and there was less compliance work than before. We had paralegals covering most of the licensing. Beyond that, it was just deals and deals and deals.

2020

This was the first year that Oregon passed the $1 billion sales mark (cresting at $1.1 billion), driven by COVID-related factors. The pool of retail licensees continued to grow, but other license categories remained static. OLCC finally streamlined its application process to some extent, a theme the Commission would return to in future years. OLCC also adopted a short-lived “fix it or ticket” approach to certain rules violations, and enacted a ban on certain vape products.

We were still doing a lot of M&A work, most memorably for a private equity firm that swooped in to buy and operate expansive verticals; and which five years later, we put into receivership. Other clients plodded along; but with prices still low, it was a volume proposition up and down the supply chain. Overall, Oregon cannabis M&A really peaked around this time. We also saw renewed interest from tribes, including intergovernmental agreements between the Cow Creek Tribe and Oregon.

Wildfires were terrible in the fall, with one in every five licensed marijuana businesses (or 408 businesses) in evacuation protocols. A large number of producers were forced off site entirely. The fires hit the hemp grows hard too, as they were heavily concentrated in the affected areas. It was a terrible time for many outdoor hemp and marijuana licensees, many of whom lost crops and equipment, and were un- or underinsured.

Unlike the THC market, the hemp market continued to sputter. Biomass pricing hovered at $2.50 or less per pound, versus $40 to $45 just two years prior. We still had many litigations in the office arising from businesses failing and investors losing money. Some of the work also involved SBA lending issues and bankruptcy proceedings, which was novel in the cannabis space.

I had been writing about international cannabis on the blog for a while, and we had some interesting matters come through the office. One of them required us to register with DOJ under the Foreign Agents Registration Act; others involved battling Customs and Border Patrol on wrongly embargoed shipments. The firm was uniquely suited for all of that, with our international trade lawyers lending a hand. I felt I was learning a lot.

Finally, this was the year that Oregon’s Measure 109 and Measure 110 passed. I was somewhat critical of Measure 109, which created a cottage psilocybin services industry, and which we would advise on in coming years. Measure 110 decriminalized possession of all drugs in small amounts. That experiment faltered, though, and the legislature rolled it back four years later. They did leave in provisions that siphoned off marijuana tax revenue for addiction services.

2021

Pricing and regulated marijuana sales plateaued in 2021, although the pool of licensed retailers continued to grow, from 719 to 760. The number of producers also increased from 1,177 to 1,388—which wasn’t needed at all. But OLCC’s streamlined licensing process was cutting through the backlog, following a very pregnant three-year “pause.” All in all, the industry continued to grow, despite a challenging labor market.

During this time, we helped people buy and sell producer licenses in the $250K – $300K range. A few years later, prices would fall as low as $30K. One of our clients liquidated something like 6 licenses on adjoining tax lots around this time; and though his timing was impeccable, he was arrested driving weed around Texas shortly thereafter. He went bust entirely. Anyway, many of the license buyers were Eastern European around this time; Chinese nationals were another sizable demographic and eventually moved into the lead.

“Artificially derived cannabinoids” were in the regulatory crosshairs, and OLCC was tasked with regulating these compounds. OLCC and ODA also got more enforcement funding, and launched Operation Table Rock. It targeted mostly southern Oregon grows, and predictably found a majority of licensed hemp producers growing marijuana. The legislature then met in a one-day special session to grant $25 million more to enforcement. I wrote that it “wouldn’t be enough,” and it wasn’t.

Certain administrative and criminal litigation ensued, though we didn’t have any of that here in the office. On the national level, the enshittification of hemp was well underway, with delta-8 and other intoxicating products being shipped nationwide under dubious color of law and with scant regulation. We decided as a law firm not to take that work, which means we decided to leave a lot of money on the table. I’m still good with that.

I got into a groove of taking on expert witness matters in state and federal court, which got me back to my litigation roots and was fun. I ended up testifying before a jury in one of them, and submitting a report for federal court use in another. All of these were disputes on the standard of care for lawyers in the cannabis space. Strikes and gutters as they say.

Some big names made the news in locally 2021. Dutchie, the cannabis Ecommerce platform out of Bend, raised an impressive $350 million in a closed Series D, at a $375 billion value. Curaleaf, which we later represented on international cannabis shipping, was sued up and down for selling a THC product in CBD packaging—among other things. And GoldenLeaf, the first Oregon cannabis outfit to roll up onto a Canadian stock exchange, came back from the dead to acquire five Home Grown Oregon stores.

We opened a New York office, which was fun and lasted a couple of years. I was also cited by U.S. Senators Cory Booker and Elizabeth Warren in correspondence to U.S. Attorney General Merrick Garland, regarding a plea to decriminalize cannabis.

But my favorite lawyering memory, ever, was being invited to speak for NORML down in Key West, Florida that December. After my presentation—but before we went for beers with a judge who had played himself in The Wire—I sat at a folding table in the back, next to an older gentleman. He was wearing a tank top and a Support the Troops cap. He said well done and shook my hand, and introduced himself as Phil Hirschkop. There was something about the interaction; I Googled him under the table; I damn near blacked out.

2022

The pandemic era tailwinds petered out, and annual Oregon sales fell to under $1 billion. Our retail clients began to report less demand for marijuana flower specifically, and adjusted to meet growing demand in the edible and cartridge categories. Wholesale pricing dipped below the 2018 market nadir, which was a shock to many operators.

House Bill 4016 passed, enacting a sweeping moratorium on new cannabis licenses in the state. This was a big deal! There were grandfathering provisions and such, but HB 4016 was a formal enactment of what OLCC had been trying to do—and what industry had been clamoring for—for years. At last, OLCC had the statutory authority to pull the plug.

OLCC also started talking tough about “bad actors” in the space, and the Commission’s practice of allowing these businesses to sell their licenses while facing revocation proceedings, all but faded to black. In concert with HB 4016, this policy change seemed informed by an underlying goal to cull licenses. That said, the State also rolled out a limited social equity program, where “qualified applicants” could receive license preference in certain contexts. From what I can tell, it never had much impact.

OLCC stopped complying with public records requests around this time, pleading organizational and staffing issues. After some back and forth, we dragged them before the Oregon DOJ. The system was eventually cleaned up, and I’m pleased to report that it continues to work as it should. The other cause I undertook in 2022 was abuse of service agreements, after seeing a series of clients damaged.

Around the county, a few of our lawyers were invited to legislative panels in states looking at cannabis regulation. We shared our thoughts there and on the blog. I started going after President Biden a fair bit too, for failing to meet his campaign promises on cannabis. He would eventually initiate an ill-fated rescheduling process, and issue some pardons. None of that squared with his promises (“decriminalization”), and it felt like a big chance missed.

Beyond cannabis, we were working with psilocybin business under Oregon’s Measure 109, and writing about psychedelics on the firm’s Psychedelics Law Blog. There was a resident ownership requirement there, like the early days of cannabis, so naturally people started gaming it. I was also invited to write a separate piece for a Harvard Law journal online. They flew me out to speak to the students—another thing I never could have imagined doing.

2023

Oregon sales fell again coming off COVID peaks, and the number of licensees finally fell too. Tracking data, I continued to note a years-long trend of consumers migrating away from flower, toward edibles and other products. That trend continues today.

I started speaking up on behalf of smaller businesses locally early in the year—they were taking it in the shorts from larger outfits and from OLCC. And I felt so badly for some of them.

Things really came to light when the La Mota scandal broke early in the year. That chain wasn’t paying its share of taxes, or its workers or vendors per widespread allegations. OLCC also let them skate following major compliance citations that would have sunk most anyone else. La Mota did have the Oregon Secretary of State quietly on payroll, we learned, which led to her ouster from public office.

Launching off that scandal, I wrote a critical piece regarding OLCC’s disparate treatment of large and small operators. A lawyer named Amy Margolis called me on behalf of Nectar, another chain operator, requesting I pull the piece. I declined. This resulted in a shabby ethics complaint against yours truly. The Bar swatted it away; Nectar appealed; and Nectar lost again.

Finally, another larger operator, Chalice, went belly up and pursued a coordinated receivership workout with its related, Canadian creditors. Local assets were eventually sold off to company insiders, who started anew. The optics on that one were also terrible, with many small operators getting shafted on payments. Receivership is an equitable remedy, of course, but the old saying is still apt: “it’s not a court of justice, it’s a court of law.”

For its part, OHA had a rough year, too, after passing a rule to mandate aspergillus testing. The rule was challenged by industry, and it was “stayed” pending judicial review. Rather than defend its rule at a hearing, OHA withdrew it, and abandon the effort. Setting aside any debate on public health, this was a real boon for the consolidated Cannabis Industry Association of Oregon.

2024

Sales and pricing remained relatively static, and the industry continued to limp along. In that respect, Oregon was similar to all of the established states, and the western states in particular. Croptober came in with Oregon’s largest METRC harvest ever at 5,733,288 pounds, which was a full 900,000 pounds more than the same month in 2023. Prices predictably suffered, though I’m guessing not all of that weed stayed in state.

We absorbed a couple of boutique cannabis firms at this time; or parts of them. Like operators and other vendors, cannabis law firms were on the decline. The small firms were withering and the larger firms—which had entered the space late—were exiting early. On the client side, we put a couple of larger outfits into receivership.

That fall, OLCC sent enforcement notices to seven of the eleven testing labs regarding THC inflation. This issue was getting a lot of coverage nationally; the local investigation had been going for a while; and the notices were no surprise. We saw a couple of labs shutter as a result.

A few notable rules landed in 2024 as well. Ballot Measure 119 took effect, which required all OLCC retailers, processors and labs to sign a labor peace agreement with a “bona fide labor organization.” I was relentlessly critical of the Measure on the blog, calling for a challenge. That finally happened and BM 119 was declared unconstitutional—that case is still up on appeal. Finally, we got new testing rules for hemp, and a bill making OLCC’s licensing moratorium permanent.

Federally, we had elections of course. Elections with consequences. Donald Trump was re-instated as President, and the Republican Party claimed majorities in both houses of Congress. This was generally viewed as unwelcome news for the cannabis industry, and for Biden’s flawed rescheduling effort. Everything came to a head a few weeks into 2025, which is where I’ll leave off.

2025

If you made it this far, thanks and I applaud you. My 2025 “State of the State” post on Oregon cannabis can be found here. It gives a solid overview of how things went last year, and where we stand today.

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