💸 The Tape

For years, the biggest U.S. cannabis operators have been building real businesses while paying (or not paying) taxes as though they were running criminal enterprises. As of last week, that contradiction started to unravel.

On April 22, 2026, the Department of Justice and the DEA issued a final order moving state-licensed medical marijuana and FDA-approved cannabis products from Schedule I to Schedule III of the Controlled Substances Act — the first meaningful shift in federal cannabis classification in over five decades. The order, issued under authority tied to the UN Single Convention on Narcotic Drugs, delivers on President Trump's December 2025 executive order directing the Attorney General to expedite rescheduling. A broader administrative hearing on reclassifying all marijuana to Schedule III is set to begin June 29, 2026.

The implications are enormous — and for the three largest multi-state operators in the country, Curaleaf, Green Thumb Industries (GTI), and Trulieve, the impact could be transformational.

The 280E Albatross, Lifted

The single most consequential effect of medical marijuana's move to Schedule III is the elimination of Section 280E of the Internal Revenue Code for qualifying operators. Enacted in 1982 to prevent drug traffickers from deducting business expenses, 280E has been weaponized against state-legal cannabis companies for years, prohibiting them from claiming the ordinary deductions — rent, payroll, marketing, administrative costs — that every other American business takes for granted.

The result has been effective tax rates that, according to Whitney Economics, have exceeded 70% for some operators. Since 2018, the cannabis industry has paid an estimated $15 billion in excess 280E-related taxes.

For the big three MSOs, the math is staggering.

Trulieve generated $1.18 billion in revenue and $427 million in adjusted EBITDA in 2025, with a 36% EBITDA margin and $228.6 million in free cash flow. Yet the company still carries an estimated $668 million in uncertain 280E tax liabilities. CEO Kim Rivers called the rescheduling order the "first ever meaningful policy shift related to cannabis in the history of America," noting that it removes the punitive tax burden, opens a pathway for DEA registration, and enables research using actual state-available medical cannabis products. At roughly 4x adjusted EBITDA, Trulieve's valuation has been compressed by the very regulatory uncertainty that just began to clear.

Green Thumb Industries — fresh off authorizing a $150 million share buyback funded entirely from operating cash flow — has been vocal about 280E's distortive effect. CEO Ben Kovler has said the company's stock price "continues to serve as a barometer for federal action." The elimination of 280E would immediately improve GTI's after-tax margins and free up capital that has been absorbed by a tax code never intended to apply to legitimate, state-licensed businesses. With a disciplined operating model and one of the strongest balance sheets in U.S. cannabis, GTI is positioned to compound the benefit of 280E relief faster than most peers.

Curaleaf, the largest cannabis company in the world by revenue, recently authorized an $83 million buyback of its own — a signal of confidence that takes on new significance in a post-280E world. Chairman and CEO Boris Jordan has consistently framed the company's strategy around being ready to scale when federal policy catches up. That moment has arrived, at least for the medical side of the business.

What This Means — And What It Doesn't

It's important to be precise about scope. The rescheduling applies specifically to FDA-approved marijuana products and marijuana subject to a qualifying state medical license. Recreational marijuana — even in states where it's legal — remains Schedule I. That means operators with dual medical and recreational licenses face an immediate complexity: 280E relief applies to their medical operations but not their adult-use sales. How the IRS interprets and implements that distinction will matter enormously, and formal guidance is still pending.

There's also a timing question. Tax advisors are watching closely to determine whether 280E relief applies immediately, retroactively to the beginning of 2026, or only to tax years beginning after the rescheduling takes effect. The difference could represent hundreds of millions of dollars in aggregate across the industry.

But even with those caveats, the directional shift is undeniable. The three largest MSOs all operate significant medical cannabis programs across multiple states. Trulieve's cornerstone markets — Florida, Pennsylvania, Ohio, and Arizona — are anchored by medical operations. GTI's RISE Dispensaries serve medical patients across its footprint. Curaleaf operates medical programs in the majority of its markets. For all three, the medical business isn't a sidecar — it's a core revenue driver that just became dramatically more profitable on an after-tax basis.

Beyond Taxes: The Normalization Signal

The financial impact of 280E relief is the headline, but the broader signal may be equally important. The federal government acknowledging marijuana's medical value could serve as a permissive signal to state-level lawmakers currently weighing cannabis legislation. It lowers the perceived risk for institutional investors, lenders, and corporate partners who have historically avoided cannabis due to federal classification concerns.

For companies like Curaleaf, GTI, and Trulieve — all of which have been navigating debt markets, refinancing facilities, and managing balance sheets under the shadow of Schedule I — the reclassification opens doors that have been locked for years. Better access to capital, more favorable borrowing terms, and the potential for eventual uplisting to major U.S. stock exchanges all become more plausible in a Schedule III world.

What Comes Next

The June 29 DEA hearing on broader rescheduling will determine whether recreational cannabis also moves to Schedule III — a development that would extend 280E relief across the entire industry and resolve the medical-versus-recreational ambiguity. Legal challenges are expected, and the IRS still needs to issue formal guidance on tax treatment.

But the trajectory is set. The three companies that have spent the longest building scale, generating cash flow, and surviving a tax regime designed to destroy them are now positioned to reap the most from its dismantling. Curaleaf, GTI, and Trulieve didn't just survive 280E — they built industry-leading businesses in spite of it.

📈 Dog Walkers

$CMND ( ▼ 0.76% ) Is Up

Clearmind Medicine is eyeing one of the FDA's most coveted fast-track labels for its lead drug candidate — and the timing couldn't be better.

The clinical-stage biotech announced it is evaluating CMND-100 (MEAI) for eligibility for the FDA's Breakthrough Therapy Designation (BTD), a classification reserved for drugs targeting serious or life-threatening conditions where preliminary clinical evidence suggests substantial improvement over existing treatments.

The case isn't hard to make on paper. CMND-100 is a non-hallucinogenic, neuroplastogen-derived oral therapy for Alcohol Use Disorder (AUD) — a condition affecting millions worldwide with notoriously limited treatment options. The company's ongoing Phase I/IIa trial has already delivered encouraging results, including a clean safety profile across escalating dose cohorts with no serious adverse events.

CEO Dr. Adi Zuloff-Shani pointed to both the clinical data and the shifting regulatory landscape as catalysts. The recent Executive Order signed by President Trump — which accelerates FDA review processes for psychedelic and neuroplastogen therapies carrying Breakthrough designations — adds a meaningful tailwind. If CMND-100 secures BTD status, it would benefit from intensified FDA guidance, rolling review, and a potentially faster path to approval.

An important caveat: Clearmind has not yet submitted a BTD request, and the FDA has not granted the designation. The company is currently assessing whether its existing data package meets the rigorous threshold. This is an evaluation, not a confirmation — a distinction worth noting in a sector where premature celebrations are common.

Still, the strategic logic is sound. A Breakthrough designation would distinguish CMND-100 from an increasingly crowded psychedelic therapeutics field and signal to investors and partners that the FDA sees something genuinely differentiated in Clearmind's non-hallucinogenic approach to treating addiction. 

🗞️ The News

📺 YouTube

Cannabis Rescheduling Is Now Official in America | TTB Weekly Recap

What we will cover:

✅ In the latest Trade To Black Weekly Recap presented by FRE Pouch, Shadd Dales breaks down one of the most important weeks the cannabis industry has seen in decades.

The headline—cannabis rescheduling is now official. The Department of Justice, led by Acting Attorney General Todd Blanche, has moved certain cannabis products from Schedule I to Schedule III. It’s a major shift—but not across the board. Medical cannabis operators stand to benefit immediately, while adult-use remains federally illegal.

From there, we shift to Virginia, where Governor Abigail Spanberger now faces a key decision that could determine whether adult-use cannabis sales launch in 2027—or get delayed again.

We also look at federal momentum, with Hakeem Jeffries saying the votes exist for reform, while Cory Booker continues pushing for full legalization beyond rescheduling.