Marijuana Rescheduling: Trump's Kessler Move Markets Missed

Marijuana Rescheduling: Trump's Kessler Move Markets Missed

Late Monday night, the President posted a thank-you note on Truth Social. It named Howard Kessler as "my friend and Advisor on Aging Healthcare." Fourteen posts went out that night. This was the one that mattered for our sector, and almost nobody noticed until The Marijuana Herald ran it Thursday.

$MSOS closed at $4.45 on Tuesday. That's 39% below the $7.25 print from December 18, the day Kessler stood beside Trump in the Oval Office for the rescheduling order. The man who got that order signed now holds a title inside the administration. The sector trades like the order never happened.

We don't think the market is reading the tea leaves. So we'll read them.

Who Howard Kessler is

Short version: he's the reason there was a December executive order at all.

Longer version. Kessler is 74, lives in Palm Beach and is a Mar-a-Lago member. He made his money in plastic. In the early 1980s he pioneered the affinity credit card at MBNA, the co-branded cards tied to colleges, teams and alumni groups. He helped grow MBNA from a startup into a $35 billion sale to Bank of America. He then founded The Kessler Group, which still advises banks, credit unions and payment networks. Trump put it this way on Monday: an innovator who changed the financial services business, now bringing that energy to healthcare.

He's also a serious philanthropist. He and his wife Michele started the Kessler Family Foundation in 1994. They funded the Cannabis Care Support Program at Dana-Farber. They've given seven figures to Ariadne Labs and the Brigham's internal medicine residency. And he's a leukemia survivor who used cannabis-derived therapies to get through chemo. That's the story RFK Jr. pointed to at the signing when he said that without Kessler, "we wouldn't be here today."

The Trump friendship runs deep. Kessler has been in the orbit since at least 2005, and he was at the wedding to Melania. Trump called him "my Howard" at a White House reception in 2017. At the December signing, the president told the room his friend looks better than he did 20 years ago.

In 2019 Kessler founded The Commonwealth Project to bring medical cannabis and CBD into mainstream senior care. He ran pilot programs at senior living facilities in Florida and New York. He made the case to Bret Baier on Fox in June 2024. In September 2025, Trump reposted the project's CBD-for-seniors video. Three months later came the order. By April, Dr. Oz had a Medicare CBD pilot up and running and credited Kessler by name. CNBC's reporting on the year-long push behind the orderreads like a case study in how to move a president. Kessler did it with personal ties, his own money and his own story so before you say this is about money we will say you’re wrong. This in our expert view is legacy and the last few decades are the proof.

The Common Wealth Project

Kessler's online home got a rebuild this year, and it's worth your time. Commonwealthproject.org now carries The Kessler Initiative and its Healthcare Discovery Engine. The pitch: faster, cheaper clinical evidence built on the payer-provider plumbing America already has. The CBD work is still there. So is the senior-care mission. The scope is bigger. That's a man building for the next phase of a White House role, not someone winding down a passion project.

Why the title matters for rescheduling

Trump has a pattern. When a priority stalls inside the bureaucracy, he hands it to a friend and tells the friend to get it done. No memo. A title and a direct line.

A source close to the situation put it to us this week. The Kessler appointment is "something no one is focused on." Trump wants rescheduling done, and he wants a look at descheduling too. His way of operating is to assign a friend, in this case his best friend, and let him finish the job. The source's bottom line: a resolution to the stay and a rescheduling announcement come "sooner than anyone thinks."

The title itself is a tell. Advisor on Aging Healthcare sits right on top of the Medicare CBD pilot and the senior-care argument that sold Trump on the order in the first place. Kessler now has a formal seat inside an administration that's publicly trying to get Schedule III over the line.

Trump is not happy with the delay

Here's what the sector got wrong on September 30. The day before, DEA Chief Judge Derek Julius paused the broader Schedule III hearing. Three rescheduling opponents wanted a GAO process report shoved into the record, and he gave them time to argue it. The government's response is due October 13. $MSOS dropped 11% on the day. The headlines said halted.

Within hours, a senior Trump adviser told The Marijuana Herald the president is "not happy" with the delays. He'd be reaching out to Attorney General Todd Blanche and DEA Administrator Terry Cole about speeding things up. This is the same president who turned to his own officials on camera in April and complained they were slow-walking him. The midterms are less than four weeks out. Rescheduling polls well with the voters he needs, and his White House press secretary said this summer that it's overwhelmingly popular. He wants a win he can point to. The stay just handed him a reason to lean on DOJ and DEA.

Keep the stay in proportion. It doesn't touch April's order. State-licensed medical marijuana and FDA-approved products are already Schedule III. Trulieve $TRLV restructured around that and now trades on the NYSE. The pause only delays the judge's recommendation on the broader move, and it has no end date. DEA's own lawyers asked the judge to "expeditiously recommend" Schedule III. The AG signed the April order that started the expedited hearing. The president wants it done, and he just gave the man who started all this a title.

The 10/16 opex set-up

Now the trade.

September's triple witching cleared on Friday the 18th. Whatever pin held $MSOS in the mid-4s came off with it. By Monday the 21st the ETF was pressing $5, and on the 22nd it punched through. Our Jan 2027 $5 calls went in the money that morning, and we rinsed $MSOX into the pop. Nothing happened on the news side. The hedges came off and the tape ran.

October 16 is the next monthly expiration, and the chain is lopsided. When we pulled the board on September 30, after the stay hit, the October monthly held about 90% of the open gamma. Roughly 26,000 $5 calls sat against 52,000 $6 calls. The put side was thin: about 3,600 at $5, 1,000 at $4, and nothing of size below. That shape reads like call spreads with $6 as the sold leg. Dealers short the 5s, long the 6s. Translation: $5 is the magnet, $6 is the wall, and there isn't much under $4.

Our position is simple. The October opex settles the market the same way September's did. Once those contracts expire and the hedges unwind, the tape is free to move, and the set-up is better today than it was on September 18, not worse. Then we had a hearing with no decision date. Now we have an October 13 filing deadline and a president on record as unhappy. We also have the man who got the order signed sitting inside the administration with a title. And at Tuesday's close the ETF was 12% cheaper than it was before the stay.

Our standing rule hasn't changed. Assume the news doesn't come, and trade around a core position. The cream still rises, and we'd rather own $TRLV and $GTBIF than chase names that just filed $100 million ATMs.

Bottom line

The market is treating the September 29 stay as the whole story and the October 5 appointment as a footnote. We think that's backwards. The stay is paperwork. The appointment tells you what the man in the Oval Office wants, and who he trusts to get it. When this president wants something done, he puts a friend on it. He just did.

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