Cannabis’s 280E Tax Trap May Finally Break. We’ve Heard That Before.

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By Trey Thoelcke Published

Quick Read

  • Section 280E forces U.S. cannabis operators to pay effective tax rates above 70%, an existential burden that a move to Schedule III would immediately eliminate.

  • MSOS rallied 99% on rescheduling hopes, but prediction markets price just 18% odds by July, and TLRY has shed 97% from its peak.

  • Act now: the analyst who called NVIDIA in 2010 just named his top 10 AI stocks — and Tilray Brands didn't make the cut. Grab the names FREE today.

Cannabis’s 280E Tax Trap May Finally Break. We’ve Heard That Before.

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While cannabis investors finally have an expedited DEA administrative hearing on the calendar and a fresh Schedule III pathway in motion, Wall Street has stood at this exact intersection before. The pure-play U.S. cannabis proxy, AdvisorShares Pure US Cannabis ETF (NYSEARCA: MSOS), has vaulted 99.2% over the trailing year on rescheduling hope, yet still trades 81.0% below its September 2020 launch price. The pattern of euphoria followed by collapse has been the only consistent feature of this trade.

The Regulatory Pivot

The catalyst this time around centers on Section 280E. That single line of the tax code denies cannabis sellers the ordinary business deductions every other operator takes for granted, taxing them on gross profit rather than net income, and pushing effective tax rates above 70% for U.S. multi-state operators. A move from Schedule I to Schedule III would remove that burden. The DEA’s expedited hearing began June 29, 2026, with a conclusion targeted for mid-July and a potential final rule in the Federal Register to follow.

Prediction Markets vs. Historical Rhymes

The prediction-market tape tells a different story. The Polymarket contract on rescheduling by today’s close implies a 0.55% probability. The contract for the end of July prints 18.5%. The year-end contract prints 23.3%, having fallen 9.65 cents over the past week. An earlier market resolving on rescheduling by March 31 closed at zero. Traders putting cash behind their convictions are pricing failure.

What’s particularly notable is how cleanly the setup rhymes with prior cycles. The 2018 Canadian legalization rally sent Tilray Brands (NASDAQ: TLRY) above $223 on a split-adjusted basis. SAFE Banking introductions starting in 2019 stalled in the Senate. The 2021 post-election rally faded. The 2024 DEA rescheduling proposal disappeared into administrative limbo. Canopy Growth (NASDAQ: CGC) crested above $241 in mid-2021 and now changes hands at $0.99, a 99.6% drawdown over five years. Tilray has shed 97.5% on the same clock.

The Canadian Disconnect and Punishing Fundamentals

Worth flagging is the structural quirk: Tilray and Canopy are Canadian licensed producers and are not themselves subject to 280E. Their share prices, however, have moved in lockstep with U.S. reform sentiment for the better part of a decade. The AdvisorShares ETF is the cleaner proxy because it owns the operators actually paying the punitive tax, with Curaleaf at 12% of net assets as the largest position and TerrAscend at 3% behind it. The fund carried $729.19 million in net assets as of the latest filing, with a defensive 7% cash position held in BlackRock Treasury Trust.

Operator economics underneath the narrative are punishing. Tilray, with its more favorable Canadian tax treatment, posted a fiscal third-quarter net loss of $25.23 million on $206.73 million in revenue. Its trailing 12-month EPS came in at −$0.24. Canopy Growth’s most recent quarter delivered $71.25 million in revenue against a net loss of $154.72 million, with an accumulated deficit of C$11 billion, per the company’s recent 8-K filing. Adjusted EPS missed expectations by 566.67%.

TLRY earnings quotes

The 280E Unlock and the Retail Divide

For the U.S. operators inside the AdvisorShares fund, 280E relief would be a genuine structural unlock. Cash flows currently consumed by the IRS would land on the income statement, valuations would compress against actual earnings rather than gross profit, and the discount that cash-strapped MSOs face when raising capital would narrow. The math is straightforward. Timing has shredded capital in this sector for eight straight years.

The retail sentiment reflects the familiar split. WallStreetBets posts in early June carried sentiment scores of 90 in connection with the latest MSO uplisting catalyst, with one trader documenting a $2.1 million MSOS position. Yet Tilray’s most recent tracked Reddit post showed a sentiment score of 8 on a thread titled “What’s the buy you regret the most?” Euphoria and exhaustion live in the same forum.

Long term, rescheduling will eventually occur, and U.S. cannabis operators will escape 280E. Markets typically reward structural reform once the rule actually appears in the Federal Register. The historical pattern shows cannabis stocks pricing the arrival multiple times before delivery, with each false dawn leaving the next entry point lower than the one before. Tilray’s $9.66 analyst target is well above the most recent close, and Canopy’s $1.22 target is only marginally above the current price.

The verdict from history is clear: the catalyst exists, the hearing is on the calendar, and the prediction-market tape is pricing failure for a reason.

 

Contact [email protected] for any questions or corrections.

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About the Author Trey Thoelcke →

Trey has been an editor and author at 24/7 Wall St. for more than a decade, where he has published thousands of articles analyzing corporate earnings, dividend stocks, short interest, insider buying, private equity, and market trends. His comprehensive coverage spans the full spectrum of financial markets, from blue-chip stalwarts to emerging growth companies.

Beyond 24/7 Wall St., Trey has created and edited financial content for Benzinga and AOL's BloggingStocks, contributing additional hundreds of articles to the investment community. He previously oversaw the 24/7 Climate Insights site, managing editorial operations and content strategy, and currently oversees and creates content for My Investing News.

Trey's editorial expertise extends across multiple publishing environments. He served as production editor at Dearborn Financial Publishing and development editor at Kaplan, where he helped shape financial education materials. Earlier in his career, he worked as a writer-producer at SVE. His freelance editing portfolio includes work for prestigious clients such as Sage Publications, Rand McNally, the Institute for Supply Management, the American Library Association, Eggplant Literary Productions, and Spiegel.

Outside of financial journalism, Trey writes fiction and has been an active member of the writing community for years, overseeing a long-running critique group and moderating workshop sessions at regional conventions. He lives with his family in an old house in the Midwest.

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