The Ballad of Howdy Hat

Back when I was a kid, getting marijuana wasn’t a transaction. It was a full-blown adventure. A quest. It was The Goonies, but instead of One-Eyed Willy’s treasure, we were hunting for a dime bag that was mostly stems and seeds.

Luckily, I was never the guy to “have it” or even the guy who “got it.” I had friends for that. Frankly, it was my friends that would have turned me on to any drug. We were the latchkey generation, raising ourselves on MTV and apathy, and the illicit nature of it all was half the fun.

When I was a teenager living in the granite-gray stagnation of New England, I had a friend named… well… let’s just call him “Howdy Hat.”

Howdy Hat was living in Charlestown, NH, but his soul—and his backstory—was from “the south.” He didn’t have an accent, but he was basically exactly who you think of when you visualize the opening riffs of a Lynyrd Skynyrd song. He was denim. He was leather. He was grit.

Howdy Hat was a blast all the time. He was sharp, too. Very smart. Probably so smart he got bored with the mundane curriculum of public high school. While the rest of us were worrying about SATs or prom dates, Howdy was operating on a different frequency entirely.

The thing about Howdy Hat is that he was open about having marijuana. And I don’t mean “whispering in the locker room” open. I mean bold.

He was so transparent that the teachers all knew he was “a stoner” and, miraculously, didn’t seem to care. Why? Because he wasn’t all “Beavis and Butthead” about it. He didn’t giggle at the word “wood.” He didn’t act like a burnout. He carried himself with a specific kind of dignified rebellion.

Howdy Hat would always just “light up a doobie” like a cigarette. No hiding behind the bleachers. No spraying Ozium frantically in a car. I remember thinking how “risky” and “badass” that was. After all, “pot” was “illegal.” It was a “big deal.” It was the D.A.R.E. officer’s worst nightmare.

We felt like outlaws because the government told us we were. And Howdy Hat was our Billy the Kid.

Flash Forward: The Corporate Kush Era

Flash back to 2025. Have you walked through Manhattan lately? It’s a trip. Every other store is a place to get pot now. It’s not a sketchy hand-off in a Taco Bell parking lot anymore; it’s an Apple Store experience.

You walk in, there are tablets, “budtenders” who know more about terpenes than I know about my own family history, and sleek packaging that looks like it belongs in a museum.

Even Mike Tyson is in on it. You can literally buy a gummy shaped like Evander Holyfield’s ear that he bit off. That is where we are as a society. We are munching on gelatinous ears legally in broad daylight. If you told teenage me that Iron Mike would be the face of mellowing out, I would have told you to lay off the whippets.

I always find it funny coming from New England where every state (except the “Live Free or Die” state… ironically) has made it legal to purchase. New Hampshire, in a twist of stubborn irony that only New Englanders understand, remains an island of prohibition surrounded by a sea of legalization. But here in Florida… not so much. At least, not until the winds shifted in Washington.

The Donald Deals a New Hand

So, what does Trump’s executive order mean? Because let’s be honest: reality is stranger than fiction these days.

On December 18, 2025, the political landscape did a kickflip. President Trump signed an executive order targeting the reclassification of marijuana. For those of us who grew up watching politicians use the “War on Drugs” as a campaign slogan to scare suburban moms, this is jarring.

According to the reports coming out of CNN, this move is about shifting the federal stance from “this is heroin” to “maybe this has medical value.” The order directs the Department of Justice and Health and Human Services to expedite the review process for moving cannabis from Schedule I to Schedule III.

For the uninitiated: Schedule I is for drugs with “no currently accepted medical use and a high potential for abuse.” You know, like Heroin and LSD. Putting weed in there was always a lie. We knew it. Howdy Hat knew it. Now, finally, the White House knows it.

This isn’t full legalization yet—don’t go lighting up on the White House lawn just yet—but it is the biggest hurdle to clear. It opens the doors for banking (so dispensaries don’t have to carry cash like drug lords), tax deductions for businesses, and interstate commerce.

The Wall Street “Green Rush”

If you want to know if something is “real” in America, don’t listen to the politicians. Watch the money. The money never lies.

Following the news of the executive order, the market went bananas. I was reading over on Barron’s that cannabis stocks, specifically Tilray and others in the sector, saw massive spikes. Wall Street woke up and smelled the kush.

Investors have been waiting for this moment for a decade. They’ve been sitting on these stocks, watching them tank, hoping for a lifeline. Trump just threw them a life raft the size of a yacht. The volatility is still there, sure, but the volume of trading tells you everything: The suits are ready to gentrify Howdy Hat’s hobby.

The Medical Research Angle

It’s not just about getting high and watching cartoons, though. There’s a serious angle here that the White House is pushing. The official statement highlights “Increasing Medical Marijuana and Cannabidiol Research.”

For years, legitimate scientists couldn’t touch the stuff because of federal restrictions. It was a Catch-22: “You can’t prove it has medical value because you can’t research it. You can’t research it because it has no proven medical value.”

This executive order breaks that cycle. It’s opening the floodgates for universities and pharmaceutical companies to actually study what this plant does. We might finally get real data on how it helps with PTSD, chronic pain, and anxiety, rather than relying on anecdotal evidence from a guy named “Spider” at a Phish concert.

The Irony of the GOP Pivot

There is a massive irony in a Republican administration pushing this through. I grew up in the Reagan “Just Say No” era. The GOP was the party of strict enforcement, mandatory minimums, and moral panic.

But the world changes. The voter base changes. Gen X is getting older. We have back pain. We have anxiety. We don’t want opioids. And frankly, the libertarian streak in the American right is finally flexing its muscle.

It’s a populist move. It’s a business move. It is the Art of the Deal applied to ganja. By taking ownership of this issue, Trump effectively steals a major talking point from the Democrats. It’s shrewd politics wrapped in rolling paper.

What Would Howdy Hat Think?

I’ve been thinking a lot about Howdy Hat since the news dropped. He was a pioneer in his own way. He didn’t need an executive order to validate his lifestyle. He didn’t need a stock ticker to tell him the product had value.

Part of me misses the danger. There was a camaraderie in the illicit. When you passed a joint in 1994, you were co-conspirators. You were trusting the person next to you with your freedom, in a small way. It bonded you.

Now? You’re just consumers sharing a product. It’s safer, yes. It’s better for society, absolutely. People shouldn’t go to jail for a plant. That’s a given.

But the “cool factor”? That died the minute Mike Tyson put his name on a gummy ear. The minute hedge fund managers started analyzing “pot futures.”

If Howdy Hat were here today, walking into a dispensary in Florida or Manhattan, I think he’d laugh. He’d look at the iPad menus, the security guards looking like Secret Service, and the curated playlists.

He’d probably buy the best stuff on the shelf, walk outside, and light it up right on the sidewalk.

Not because it’s legal now. But because he was doing it before it was cool. Before the Executive Orders. Before the stock options.

We are living in a brave new world, folks. The outlaws have become the industry leaders. The counter-culture has become the culture. And the President of the United States is clearing the runway for the green revolution.

It’s a long way from Charlestown, NH. It’s a long way from hiding behind the gym. But as the smoke clears, it looks like we might finally be getting somewhere sensible.

So here’s to Howdy Hat. Here’s to the rebels who sparked up when the world told them no. You were just ahead of the curve. And here’s to 2025—the year the government finally caught up.