He will be remembered for his many quixotic campaigns — running for governor five times, Congress twice, as well as commissioner of agriculture and attorney general.
Despite never winning a race, he was almost universally recognized as one of the best stump speakers in Kentucky politics, using his trademark humor and wit to charm the crowd. Gatewood was also known for his fearless honesty and directness, sticking by and defending his policy positions, no matter how controversial.
The one controversial policy he was known best for and that will forever be his legacy: tireless advocacy for reforming marijuana and industrial hemp laws.
In a state that glorifies its bourbon industry — ignoring the violence, crime and liver damage that sometimes comes with its abuse — Gatewood never shied away from pointing out the insanity of a government that spends millions of dollars incarcerating people for growing/using/possessing a plant that springs out of our soil and causes little harm, other than maybe lethargy, hunger and the occasional fit of incoherent babbling.
Not to mention the fact that marijuana and industrial hemp — which is virtually impossible to get high from and was a major Kentucky cash crop before being outlawed — could be a huge boost to Kentucky’s sagging farming and manufacturing industries, providing much-needed jobs and tax revenue.
But of course, Gatewood wasn’t just a leader of the legalization movement. He was also a client.
“He smoked pot like a fiend. Like a fiend, up until the day he died,” says Dea Riley, his good friend and running mate in last year’s gubernatorial race.
Gatewood was like the love child of two other Kentucky-born legends, part Abraham Lincoln and part Hunter S. Thompson. He was the towering country lawyer, the great orator who ventured into the political sphere to protect the freedom of men. And he did so, for a great part of his adult life, while being considerably high and not taking shit from anyone.
His unapologetic support for cannabis legalization and regulation may have won him statewide name recognition and national fame among pot advocates, but in the era of “Just Say No” and the War on Drugs, this did nothing to help him win elections.
In fact, it often overshadowed his efforts to bring up other important issues that plague the commonwealth, and the great deal of intellect and common sense he brought to them. This was also complicated by his unconventional ideology, as just as many people looked at his positions and called him a radical liberal as those who called him a radical conservative.
Despite those efforts, for much of his political career, many in the media, political sphere and voting public looked at Gatewood and only saw the crude stereotype: “the pot guy.” Such people dismissed him, either from irrational Reefer Nation fears, or because espousing such controversial truth excluded him from the “serious” political community and their poll-tested talking points.
In Gatewood’s autobiography, “The Last Free Man in America,” he details one of the most important moments of his life: the first time he smoked marijuana in 1968. He said the drug cured him of his crippling asthma and anxieties that plagued him throughout his youth, literally saving his life.
From that point on, Gatewood became both an active user and a defender of the benefits of marijuana.
After receiving his law degree from the University of Kentucky, Gatewood became a criminal defense attorney in Lexington in 1981. And according to those who saw him in the courtroom, whatever he ingested did nothing to impair his legal abilities.
“He’s one of the best trial lawyers I’ve ever seen,” says state Sen. Kathy Stein, who began working as a public defender in Lexington around the same time.
While noting that “he always smelled like marijuana,” Stein says, “We were always amazed by his ability to dissect a legal issue with no problem at all and clearly communicate what he thought was just to judges and juries. He charmed anyone whom he was speaking to.”
Gatewood made his first attempt at political office in 1983, running for state commissioner of agriculture. He laid out his platform for cannabis legalization and regulation, setting out on a low-budget grassroots campaign across the state, something he repeated many times. And just like his many races to follow, he lost by a wide margin.
The year after Gatewood was first introduced to marijuana in the late 1960s, a Gallup poll showed only 12 percent of Americans favored its legalization, with 84 percent opposing it. By the time Gatewood made his first few runs for statewide public office in Kentucky through the mid-1990s, not much had changed, with polls showing support for legalization hovering just above 20 percent.
With Kentucky being so socially conservative, this made his attempts to run for the highest office in the commonwealth on such a platform — while also unapologetically admitting that he partakes in it himself — a daunting task.
“Something that harmed him for so long, as far as being taken as seriously as he should have been, was marijuana,” Stein says. “He started that a long time ago, before public opinion started to change, and everyone just shrunk away in horror at the thought of legalizing marijuana.”
Though Gatewood began to expand his platform to many other issues — articulating a populist ideology that feared government intervention in people’s private affairs, yet endorsed its role in social services — he had trouble getting those ideas across to voters. Throughout his political career, he complained that the press in Kentucky did not take him seriously or give him the coverage he deserved.
Al Cross, one of the deans of Kentucky political journalism, covered Gatewood’s campaigns over the course of his career. He agrees that many in the media did unfairly treat him as an amusing sideshow, playing up the “pot guy” persona. But he suggests the somewhat limited coverage he received was often warranted due to his consistently poor chances for victory.
“My policy on third-party independent candidates was that at the start of a race, you give them as equal treatment as practicable because they deserve a chance to create a following and build support,” Cross says.
“But then as the race goes on, it’s not practical to give space to people who are running in single-digits and have no chance of getting elected, because your obligation is to inform people about the real choices in the race.”
In many races, Cross adds, Gatewood’s campaign and messaging lacked discipline and details. “Gatewood had some good ideas and a set of interesting principles,” he says. “But he couldn’t really flesh them out in ways that would match up with other candidates. I think he would have been treated more seriously if he had done that.
“And I always felt a little guilty about that, because Gatewood was a very thoughtful and entertaining and highly intelligent person. I always enjoyed being around him, and he was never really satisfied with the coverage I gave him, but I think he was smart enough to know the score.”
Gatewood’s ability to get his campaign’s message out was also perpetually hampered by his inability to raise large (or even moderate) contributions, unlike his competitors.
One of his most resonant campaign themes was the corrupting influence of corporate money on both political parties. A common catchphrase blasted the unholy alliance of government officials and big business as the “petrochemical-pharmaceutical-military-industrial-transnational-corporate-fascist-elite-sonofabitches.” Predictably, said SOBs weren’t about to give Gatewood’s campaign any money when they had a good thing going with the Democratic and Republican establishment.
However, Dea Riley says that what hurt their campaign’s fundraising ability the most was the label of Gatewood as the perennial losing candidate.
“People thought that pot was the issue that affected Gatewood, but the hardest issue that we faced and had to overcome was that he had run and lost so many times,” Riley says. “People were hesitant and didn’t know how serious he was. We heard that a great deal.”
When Gatewood chose Riley to be his running mate in his last gubernatorial run as an independent, she finally convinced Gatewood to tighten up his messaging. Since everyone in the state already knew exactly where he stood on hemp and marijuana, he would devote the majority of his speeches to economic issues, while not wavering one inch on his principles if asked.
But Gatewood being Gatewood, he cared so much about the issue that his mind and messaging would often drift back to cannabis without any prompting.
After Gatewood brought up cannabis four times in an interview with a newspaper editor, Riley organized a fundraiser with business leaders and implored him not to give his patented pot stump speech. Gatewood obliged and won over the crowd with his signature charm.
Later that night, the duo went to another fundraiser at a filthy dive bar, with the attendees appearing “like they just walked off death row.” Scoping out his audience, Gatewood launched into his speech on marijuana and hemp, whipping the crowd into a hooting and hollering frenzy of support.
Gatewood walked over to Riley and quipped: “Now these are my people.”
Many suspect Gatewood always knew he would lose his races but ran simply to challenge the status quo candidates. Somebody had to tell voters the straight, unvarnished truth, along with the bipartisan solutions the two parties perennially ignored.
Nevertheless, Riley says that while Gatewood might have realized some previous races were lost causes, he truly hoped he had a chance to pull off the upset in his last race this past fall.
Once again, he failed to come close, finishing with almost 10 percent of the vote. But just as always, he did it his way.
“In that respect, he was the ‘the last free man in America,’” Cross says. “He didn’t have to kowtow to anybody, and certainly he didn’t have to send out templates.”
Gatewood was a hero to many liberals for taking a stand against the powerful coal industry by opposing mountaintop removal mining, supporting cannabis reform, decrying the influence of money in politics, and advocating government programs to help students and the working class.
He was also a hero to many conservatives and Tea Partiers for advocating limited government, opposing abortion rights, defending gun rights and militias, and even espousing a paranoid fear over the United Nations infringing on the sovereignty of America. In many ways, he was a prototype of Ron Paul, before most Kentuckians had heard of him, and often referred to himself as the original Tea Partier.
Because of all of those contrasting positions, many on the left and the right just couldn’t come around to fully supporting him.
“Gatewood was one of those people that everyone lived through vicariously,” Riley says. “He was a man who didn’t pull any punches, told everybody exactly what he believed. Damn the torpedoes and damn the judgment, he would let it all hang out. And I think all of us in part want to do that.”
But even those who didn’t agree or vote for him admired him for being such an engaging, humorous and uncompromising original.
“He never tried to hoodoo anybody,” Sen. Stein says. “You know his famous line: ‘If I was going to lie to you, I’d already be governor.’”
Following news of his death, an outpouring of praise for Gatewood swept over the state from leaders of both parties, including those who received most of his barbs over the years, such as Gov. Steve Beshear and Mitch McConnell.
“I think Kentuckians fail to understand the damage that money has done to their political system, and Gatewood was kind of an antidote to that,” Cross says. “And I think that’s why a lot of people loved him.”
It should also come as no surprise that Gatewood fared the best in his last race in the two counties that knew him best — Nicholas County, where he grew up, and Fayette County, where he lived the last 52 years of his life — almost earning more votes in both than Republican David Williams.
Media reports have spoken about Gatewood’s extremely generous and charitable nature, as he would take time out of every Sunday morning in Lexington to give money and encouraging words to homeless people. And even though Gatewood faced devastating personal financial issues in his later years, he often provided legal services free of charge to those who couldn’t afford a lawyer.
As for his political legacy in Kentucky, most agree it will be how far ahead of the times he was on legalizing marijuana and industrial hemp.
National polls in recent years have shown a dramatic shift in public opinion, with more than 70 percent of Americans favoring the legalization of medical marijuana (with 16 states having already done so). And last fall, for the first time in history, a major pollster (Gallup) showed a majority of Americans supporting full legalization.
While state Sen. Joey Pendleton’s bill legalizing industrial hemp will again face a tough battle in Kentucky — as will the bill Stein intends to file along with Sen. Perry Clark that would legalize medical marijuana — major progress was made last year with the passage of legislation that reduced criminal sentences for marijuana possession. And for the first time in history, both candidates for commissioner of agriculture last year supported industrial hemp, with the victor, James Comer, now promising to lobby for its legalization.
“(Legalizing industrial hemp) is almost a no-brainer for the state,” Cross says. “And I wish that the police would just wake up to the reality of it. That would be a good legacy for Gatewood, because hemp has always been a potentially valuable crop, and I’d like to see them do something with it.”
“I think we’re all going to learn, and I think it will be his legacy, that Gatewood was right,” Riley says. “But I just feel so blessed that I knew it without having to wait 30 years.”
During a public memorial in Lexington last Thursday, an overflowing crowd paid a final tribute to the Last Free Man, with Mayor Jim Gray and U.S. Rep. Ben Chandler sharing their Gatewood stories. Family also spoke, shedding light on the private side of Gatewood, a father who always showered his children with love and support.
His daughter Molly spoke of her father’s reply when she once asked him what he would do if he actually won and became governor: “I can’t wait to get up there and tell people that they’re free and they don’t have to be afraid anymore.”