The Contradiction Machine: Donald Trump's 36-Year War With the War on Drugs
From a 1990 Miami luncheon calling drug enforcement 'a joke' to a 2025 rescheduling executive order his own DOJ is undermining — a definitive history of America's most contradictory president and the plant he can't quite figure out.
In April 1990, a brash New York real estate developer stood before 700 people at a Miami Herald luncheon and called American drug enforcement "a joke." He argued that full legalization of all drugs — not just cannabis — was the only rational path forward, and that tax revenue from a regulated market should fund education programs. The man's logic was clear, his conviction absolute: prohibition was a losing strategy, and the only way to win was to stop fighting.
Thirty-six years later, that same man sits in the Oval Office, having signed an executive order to reclassify cannabis from Schedule I to Schedule III — while his attorney general simultaneously directs federal prosecutors to "rigorously" enforce marijuana possession laws on federal land.
Welcome to the Donald Trump cannabis paradox: the most significant shift in federal marijuana policy since Nixon, delivered by an administration that is simultaneously escalating the drug war it claims to be unwinding.
This is the full story.
Act I: The Libertarian (1990–2015)
Before there was a political brand to protect, Donald Trump had a remarkably coherent position on drugs. At that 1990 Miami Herald luncheon, he didn't hedge. He blamed America's drug crisis on politicians who lacked courage and argued that legalization, paired with aggressive public education funded by tax revenue, was the only viable strategy.
It wasn't a one-off. In his 2000 book The America We Deserve, Trump reiterated his reform-minded stance while noting that he had never personally used drugs or alcohol — a fact he attributes to the death of his brother Freddy, who died of alcoholism in 1981 at the age of 43.
This is a critical biographical detail that often gets overlooked in cannabis policy discussions. Trump's abstinence from all substances isn't casual preference; it's rooted in genuine personal tragedy. Freddy Trump's death shaped his brother's relationship with intoxicants permanently. Yet even that deeply personal experience didn't lead the pre-political Trump toward prohibitionism. Instead, he reached the opposite conclusion: if enforcement doesn't work, stop pretending it does.
By 2015, as he launched his first presidential campaign, the rhetoric had softened considerably. At a Nevada rally that November, he told supporters that marijuana legalization should be a state-level decision and called for more research into the effects of recreational use in states like Colorado. In a February 2016 Fox News interview, he expressed conflicted feelings but landed firmly on the medical side: he said he was "in favor of" medical marijuana "a hundred percent."
This is the Trump the cannabis industry thought it was getting.
Act II: The Drug Warrior's Cabinet (2017–2020)
Once in the Oval Office, Trump's first term became a case study in the distance between a president's instincts and his appointments.
Jeff Sessions and the Cole Memo. The single most consequential cannabis decision of Trump's first term wasn't made by Trump — it was made by his attorney general. Jeff Sessions, a career drug warrior who once joked that he thought the Ku Klux Klan "were OK" until he learned they smoked marijuana, rescinded the Cole Memo on January 4, 2018 — one day after California's recreational market went live.
The Cole Memo, issued under Obama's DOJ in 2013, had been the functional truce between federal prohibition and state legalization. It directed federal prosecutors to deprioritize marijuana cases in states with regulated legal markets. Its removal sent a shockwave through the industry, chilling investment and triggering bipartisan backlash.
Colorado Senator Cory Gardner, a Republican, responded by threatening to block 20 DOJ nominees until Trump personally assured him that states' rights on cannabis would be respected. Trump reportedly made that deal. But the damage was done — the signal from the DOJ was clear, even if the president's personal views pointed elsewhere.
Tom Marino and the "Drug Czar" debacle. Trump's nominee to lead the Office of National Drug Control Policy was a former prosecutor with a well-documented track record of opposing criminal justice reform. He once advocated for hospital-style institutionalization for anyone convicted of even minor drug offenses. Marino ultimately withdrew his nomination amid a scandal involving his role in passing legislation that weakened the DEA's ability to combat opioid distribution — a stunning irony for someone positioned as a drug warrior.
The VA stonewall. Throughout Trump's first term, the Department of Veterans Affairs refused to allow its physicians to recommend medical cannabis to patients, even in states where it was legal. Studies had indicated that cannabis could be an effective therapy for PTSD, but the VA maintained its prohibition posture. The most the agency would concede was that veterans wouldn't lose their benefits for using medical marijuana — a bare minimum that still left many afraid to try it.
The pardons that weren't. Despite branding himself as a criminal justice reform president — largely on the strength of the First Step Act — Trump pardoned only two people incarcerated for cannabis offenses during his entire first term. For a president who claimed to believe marijuana policy should be left to the states, the clemency record told a different story.
Yet buried in this first-term record are two genuinely significant achievements that complicate the narrative.
Act III: The Farm Bill and the Right to Try
The 2018 Farm Bill signed by Trump on December 20, 2018, is arguably the most important piece of cannabis-adjacent legislation in a generation. Championed by Senate Majority Leader Mitch McConnell, the bill removed hemp — defined as cannabis with less than 0.3% delta-9 THC — from the Controlled Substances Act entirely. For the first time since 1970, a variety of the cannabis plant was federally legal.
The downstream effects were enormous. Hemp cultivation exploded. CBD products proliferated. And a loophole in the bill's language inadvertently legalized several psychoactive cannabinoids — delta-8 THC, delta-10, HHC, and THCP — that would go on to create a multi-billion-dollar gray market. That loophole persisted for seven years before Congress tightened the hemp definition in November 2025, a change set to take effect in November 2026.
The Farm Bill is often credited to McConnell, and rightly so. But it required Trump's signature, and he provided it without hesitation. It was the first change in the federal classification of any cannabis plant since the Controlled Substances Act was enacted.
The Right to Try Act, signed on May 30, 2018, is where the cannabis story gets philosophically interesting. The law allows terminally ill patients who have exhausted all approved treatment options to access experimental medications that have completed Phase I FDA safety trials but haven't yet received full approval. It effectively bypasses the FDA's traditional gatekeeping function for patients with nothing left to lose.
The law itself makes no mention of marijuana. But the legal framework it establishes — that terminally ill patients have a fundamental right to try substances the federal government hasn't fully approved — carries a philosophical resonance that cannabis advocates have seized on. If a dying patient can access an experimental cancer drug that has cleared only initial safety trials, the argument goes, why should a patient with chronic pain be denied access to a plant that 47 states have recognized as medicine?
The parallel isn't exact, but it's powerful. And it reflects a libertarian impulse in Trump's thinking that has always been present — the belief that individuals, not bureaucracies, should make decisions about their own bodies.
The irony is that the Right to Try Act has been used sparingly. As of available records, the FDA has approved only 16 treatments through the program since 2018. Trump claimed it saved "thousands and thousands" of lives, but experts have characterized this as a significant overestimate. The FDA, which already approved 99% of compassionate-use applications before the law existed, viewed it largely as redundant.
Still, the principle matters — especially when viewed through the lens of what came next.
Act IV: The Pivot (2024 Campaign)
Something shifted during Trump's 2024 campaign. Whether driven by polling data, personal lobbying, or genuine evolution, he began making cannabis-specific promises that went further than anything in his political career.
In September 2024, he posted on Truth Social that it was "time to end needless arrests and incarcerations of adults for small amounts of marijuana for personal use." He endorsed Florida's Amendment 3, a constitutional amendment that would have legalized recreational cannabis — putting himself at odds with Governor Ron DeSantis, who spent public resources opposing it.
The cannabis industry noticed. And it opened its wallet.
Trulieve CEO Kim Rivers reportedly attended a fundraiser at Trump's New Jersey golf club where rescheduling was directly discussed. Federal Election Commission filings show Trulieve donated $750,000 to Trump's inaugural committee and $250,000 to his MAGA Inc. super PAC. Curaleaf routed another $250,000 through the U.S. Cannabis Council. The American Rights and Reform PAC, funded by a coalition of major multi-state operators including Green Thumb Industries, Verano, Cresco Labs, and Trulieve, directed $1 million to MAGA Inc.
The industry wasn't just donating — it was deploying Trump-world lobbyists. Brian Ballard, widely considered one of the closest lobbyists to the president due to their three-decade relationship, was retained. So were Bryan Lanza, a former Trump administration official, and Daniel McFaul, former chief of staff to Matt Gaetz. Pro-cannabis PACs ran targeted ads on television networks known to be watched at the White House and Mar-a-Lago.
The campaign promise was explicit: rescheduling, safe banking, and respect for states' rights.
Florida's Amendment 3, despite Trump's endorsement and Trulieve's record-breaking $142 million campaign investment, failed to reach the 60% supermajority threshold required under Florida law. But the political groundwork was laid.
Act V: The Executive Order (December 18, 2025)
On December 18, 2025, Trump signed Executive Order 14370: "Increasing Medical Marijuana and Cannabidiol Research."
The order directed Attorney General Pam Bondi to complete the rulemaking process to move marijuana from Schedule I to Schedule III — a process that had originated under Biden's administration when HHS recommended the change in August 2023 and the DEA issued a proposed rule in May 2024.
The order also launched a Medicare pilot program allowing doctors to recommend CBD products to seniors, with coverage up to $500 annually. And it directed the White House to work with Congress on updating the statutory definition of hemp-derived cannabinoid products.
Trump framed it as common sense. He invoked patients with chronic pain, veterans with service injuries, and seniors struggling with age-related conditions. Howard Kessler, a Palm Beach billionaire, leukemia survivor, and longtime Trump friend who had been advocating for cannabis access for seniors since 2019, stood beside him at the signing.
But the fine print matters.
The order does not legalize marijuana. It does not decriminalize possession. It does not address criminal justice reform, expungement, or the tens of thousands of Americans still incarcerated for cannabis offenses. It does not affect recreational use in any way. Trump said explicitly at the signing that it is "never safe to use powerful controlled substances in a recreational manner."
Most critically, the order does not actually reschedule marijuana. It directs the attorney general to complete the rulemaking process — a process that involves DEA administrative hearings, public comment periods, and potential legal challenges. Legal experts note this could take years. The Congressional Research Service confirmed that the president cannot directly change marijuana's scheduling status; he can only direct agencies to consider it.
As of April 2026, marijuana remains a Schedule I substance under federal law.
Act VI: The Split Screen (2026)
Here's where the contradiction becomes impossible to ignore.
On one screen: Trump signed the most significant pro-cannabis executive order in American history, and the cannabis industry celebrated.
On the other screen: His DOJ moved in the opposite direction.
On September 29, 2025 — less than three months before the executive order — the DOJ quietly rescinded what it characterized as Biden-era guidance on marijuana enforcement. The U.S. Attorney for Wyoming announced that his office would "rigorously" prosecute cannabis possession on federal land, declaring marijuana a "public safety hazard."
Attorney General Bondi's DOJ has not merely declined to continue Biden's soft-touch approach — it has actively reversed it. Biden's categorical pardons for federal simple-possession offenses are constitutionally protected and cannot be undone. But the DOJ can refuse to support expungement, pursue new possession charges aggressively, and reinstate maximum charging policies going forward.
In February 2026, Trump signed funding legislation that explicitly prevents Washington, D.C. from legalizing marijuana — a direct intervention in local governance that contradicts his stated belief that cannabis policy should be decided at the state level.
And as of this week — April 10, 2026 — longtime Trump advisor Roger Stone told Marijuana Moment that someone within the administration is "holding up" the rescheduling process, calling it "vitally important to get this done before the next election." Meanwhile, the DEA's administrative law judge who was overseeing the rescheduling hearing has retired, and no replacement proceedings have been scheduled. Congressman Steve Cohen wrote to Bondi on March 27 — 99 days after the executive order — asking for a timeline. He has not received an answer.
The rescheduling process is stalled. Enforcement is escalating. And the industry that poured millions into Trump's political operation is still waiting for a return on investment.
The Through Line
Here is what 36 years of Donald Trump's relationship with drug policy reveals:
His instincts are libertarian. From the 1990 Miami Herald speech to the Right to Try Act to the December 2025 executive order, there is a consistent thread: Trump believes individuals should have more freedom to make their own medical decisions, and he's skeptical of bureaucratic gatekeeping. The Farm Bill, which removed hemp from the CSA, is the most concrete legislative expression of this impulse.
His appointments are prohibitionist. Jeff Sessions rescinded the Cole Memo. Tom Marino wanted to institutionalize minor drug offenders. The current acting DEA administrator, Derek Maltz, has called marijuana a "gateway drug" linked to school shootings. Pam Bondi's DOJ is prosecuting possession. The pattern is unmistakable: Trump consistently selects law-and-order figures who view cannabis through a prohibitionist lens, then acts surprised when they enforce prohibition.
His policy is transactional. The timing of the December 2025 executive order — after months of targeted lobbying, millions in donations, and ads literally aimed at his television screens — suggests that cannabis policy, for this president, is responsive to political inputs rather than driven by ideological conviction. The cannabis industry invested heavily, and it got an executive order. Whether that order produces material change is a separate question.
The War on Drugs is not over. Despite the rescheduling order, the fundamental architecture of prohibition remains intact. Marijuana is still Schedule I. Federal possession is still prosecuted. The 280E tax penalty still applies to cannabis businesses. Banking remains restricted. Interstate commerce is prohibited. And the new hemp definition taking effect in November 2026 will effectively ban most existing hemp-derived products.
Where It Stands Today
As of April 2026, the state of play is this:
The executive order exists. The rulemaking process is stalled. The DOJ is enforcing possession. The DEA has no administrative law judge to oversee rescheduling hearings. Congress blocked D.C. legalization. The hemp industry faces an existential ban in seven months. Roger Stone says someone is holding things up. Ninety percent of Americans support some form of legal cannabis. And the cannabis companies that donated millions are funding another Florida ballot initiative for 2026 while waiting for federal reform that may or may not arrive.
Donald Trump looked at the War on Drugs in 1990 and called it a joke. In 2026, the joke continues — and the punchline keeps changing depending on who's in the room.