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From Fiery Revolutionary to Sunshine State Retiree: The THC-Fueled Twilight of the Last of the Chicago 7
DUNEDIN, Florida — On the surface, Lee Weiner resembles a quintessentially blissed-out Florida retiree. He’s a deeply tanned 84-year-old Jewish guy who is always wearing flip flops and often smoking pot. His laid-back LinkedIn profile picture shows him smiling shirtless in a hot tub overlooking the ocean, photo evidence of his abiding mission to chill out.
When we first meet, on a sweltering Tuesday morning in May, he takes me through the motions of his daily Daoist practice. First, we walk a path in his gated community, stopping periodically to smell the flowers. We end at the pool, dip our toes in, then drive to one of his favorite joints: the High and Dry Grill, a breezy palapa overlooking the Gulf of Mexico’s Listerine-blue waters. It’s now just after 1 p.m., but 5 o’clock somewhere, and so Weiner orders a “jumbo” margarita, no salt. I spring for a piña colada, we both start sipping and all the world’s worries seem to wash away.
That is, until Weiner leans over to me, a mix of worry and weariness in his eyes. “I believe we are heading for a very difficult and dark time,” he exclaims.
The flowers and the tequila and the ocean breeze all help chill Weiner out, but only to a point. You see, Weiner is the last surviving member of the Chicago Seven — the famed band of anti-war organizers prosecuted for stirring up trouble at the 1968 DNC Convention. Disturbing the peace is in his bones.
Fifty-six years later, elements of that era echo out everywhere. Next week, the Democratic National Convention will return to Chicago. As in 1968, it will do so at a time of intense intraparty conflict, much of it concerning an increasingly unpopular war.
Back then, Democrats nominated Hubert Humphrey, a vice president replacing an unpopular incumbent, Lyndon Johnson, who bowed out late in the calendar. Republicans fielded Richard Nixon, who ran on a platform fusing crime, race and fear. Both candidacies were vigorously opposed by a young, radical protest movement against war, discrimination and restrictive abortion policies. This activism was largely concentrated on college campuses and prominently featured young Jewish leaders railing against their parents’ politics. Oh, and there was a man named Robert F. Kennedy on the ballot. Sound familiar?
Weiner was at the psychedelic center of this political storm. In some sense, he was its paragon: the only Chicago native of the seven and its youngest member, a lefty Jew and “a lunatic student,” in his words, who symbolized the streets, the city and the vital role academia has long played in providing the knowledge and the freedom to foment youthful revolt — and change.
The impending protests in Chicago are set to demand an end to American military aid to Israel. As many as 25,000 activists are expected to convene in Cook County, which is today home to the largest population of Palestinians in America. The impact of their actions may be immediately unclear, though many will surely deride them as extreme and counterproductive, as was the case in 1968.
What’s changed is that yesterday’s rabble-rousers have become today’s institutionalists. Despite youthful promises to the contrary, the baby boomers have largely left the counterculture for corporate jobs, comfier digs and conservative politics. This condition famously struck one of the seven, Jerry Rubin, who went from protesting capitalism on the floor of the New York Stock Exchange to becoming a Wall Street entrepreneur.
Other defendants became intoxicated by fame or deeply damaged by drugs. One of them, Rennie Davis, fell in with an Indian guru. Bobby Seale, the renowned Black Panther leader who made only a brief appearance in Chicago but was nonetheless initially charged alongside the seven, went on to write, teach and speak. (Now 87, Seale couldn’t be reached for comment.)
Unlike Seale or Rubin, Weiner never really got famous. But he never really wanted to. At a press conference during the trial, he described himself as a “technician of the revolution,” grumbling that the case “blew his cover.” He was, to be clear, far from a wallflower, accruing an additional contempt charge after furiously correcting Judge Julius Hoffman’s mispronunciation of his last name. (It’s WHY-ner, not WEE-ner.)
In the decades since the trial, Weiner has remained righteous, radical and highly attuned to the world. Unlike many boomers, he lacks cynicism and holds an abiding soft spot for “hopeium,” to borrow a Zoomer’s phrase, knowing full well that it’s an activist’s best fuel.
From the looks of his small, spare apartment, it’s also clear that he never sold out. His gated community is socioeconomically mixed, while the eponymous gate is, according to Weiner, broken about 90 percent of the time. The only tangible benefit Weiner seems to have accrued from his movement days is his funky Honda Civic, which is literally held together by tape. Weiner purchased it with some money Netflix gave him to participate in a promotional panel for Aaron Sorkin’s 2020 film, “The Trial of Chicago 7.”
When Weiner moved to the Sunshine State in 2017, he hoped to finally let go of activism, his first and forever love, and to “not be fucking furious all the time.” But he’s resisted the allure of total retirement, including by writing a political memoir called Conspiracy to Riot. That process transported him back to his past, and, via various book talks, put him in contact with a new generation of student activists. “I guess I’m retired,” he told the Chicago Tribune in 2020. “Will I write another book? Will I throw a bomb? I don’t know, it’s only the middle of the week.” Perhaps the answer lies on LinkedIn, where Weiner lists himself as an “aspiring anarcho-commie agitator.”
“I can’t just be in the audience,” he tells me, longingly, between hits of a weed pen. “It simply isn’t my style.”
Of his various vices, it’s only politics where Weiner self-identifies as a “junkie.” Like any addict, he obsesses over a system that perennially disappoints him. Every morning, he feverishly consumes news from his bedroom, sipping coffee from a Mao Zedong mug and accessing the web via a Wi-Fi network whose password is an ode to Communism. (I won’t share the full code, but it begins with “RedStar …”)
Weiner recognizes that protest is often unpopular in the moment but ultimately vindicated in the end, and he has tempered his anger towards Hamas with a clear-eyed analysis about Israel’s U.S.-backed campaign. “There’s no question — none — that there should be massive demonstrations against the slaughter in Gaza,” he says.
Weiner remains an unyielding champion of street protest, even as its efficacy has come under fire. Some argue that protest has lost its potency, while others point to state-led efforts to criminalize the act as evidence of its abiding strength. While some see protest as a tool of division, Weiner insists that the streets are both a powerful avenue to change and an antidote to isolation. “You’ve got to get out there — to yell at somebody, to hug somebody, to love somebody,” he tells me. “You have to be with people, to see their experiences and their pain and then, together, to do something about it.”
He pauses, searching for a corollary activity: “Very few people would disagree that sex is fun and vitally important,” he concludes. “My argument is that politics is the same.”
It’s a few hours after our tropical drinks, and Weiner and I are watching a blazing sunset from his Honda as we drive inland, to a seafood place called the Lucky Lobster Company. There, as Weiner noshes on his crustacean dinner, he recalls the mixture of hunger and anxiety he felt one night while locked up in Cook County Jail with his six co-defendants, awaiting a verdict.
In their holding area, a co-defendant, Tom Hayden, was readying for the revolution by practicing karate. This elicited cracks from a couple of wise guys who, it turned out, knew a mobster that Weiner’s father, Herman, worked with on a painting crew. They took a shine to the young, hungry Weiner, and bragged that they knew the assistant warden. Later that night, Weiner swears to me, he received “a food tray with Cornish game hen and wild rice.”
Among the seven, Weiner was the only one with a deep connection to the people and politics of the Second City. Weiner knew mobsters, activists, politicos and cops from his time as a community organizer, where he helped establish welfare and tenant unions, a legal aid clinic and a food co-op. His political worldview was also greatly shaped by the city’s academic environments, including Loyola, the University of Chicago and Northwestern, where, among other things, he researched how to start a revolution. (His case studies included Moses breaking the Israelites out of Egypt, and the Bolsheviks.)
Weiner sees today’s far-right attacks on higher education as a tacit admission of their importance. “Those sorts of spaces are important to play in and be free and to find out what you care about.”
In 1962, while at the University of Chicago, Weiner pledged to attend the Freedom Rides, but his grandfather interrupted these plans, sending him to Israel for a year to study at Hebrew University. “I accepted the gift, even though I knew it was my family’s way to get me back to my Jewish roots and away from the possibility of riding buses into strange and dangerous southern cities,” he recalls in his memoir.
The plan backfired, further radicalizing Weiner and paving the way for his prominent role at the convention. In Israel, Weiner visited a socialist kibbutz, broke bread with Jewish and Arab members of the state’s Communist Party, and met Jerry Rubin, his future co-conspirator and co-defendant.
Weiner later made pilgrimages to New York to see Rubin. The two would get high, see shows at the Fillmore East, and hang with emerging movement figures, like beat poet Allen Ginsberg and Abbie Hoffman, another of Weiner’s future co-defendants and a leader of the Youth International Party, or Yippies.
Appreciating Weiner’s Chicago connections, Hoffman and Rubin deputized him as a field marshal. He attempted to broker logistical agreements with cops he knew and, as backup, trained participants in what he then described as “active and mobile forms of self-defense,” fancy parlance for what essentially amounted to rolling up magazines to deter billy clubs.
Among the many miracles of the 1968 convention was that no one died. Also incredible was the ability of competing activist sects to flow into a cohesive form, even as elements of the media and American intelligence agencies tried to divide and destroy them.
“We were often taken in bad faith, seen as traitors to our country — the ‘useful idiots of the north Vietnamese,’” recalls Frank Joyce, an organizer who attended the convention and assisted with trial prep. Abe Peck, a media professor emeritus at Northwestern who covered the trial for a defunct radical newspaper called The Seed, says mass movements often grapple with a “media framing that tends to be about violence as opposed to what are the issues and what does the movement stand for.”
The Yippies managed to break through this framing with a series of satirical convention happenings. They nominated a pig named Pegasus for president and held an “Anti-Birthday Party” for President Johnson. Amid this, Ginsberg recited Hindu incantations on the shores of Lake Michigan, enriching an overall hippie ethic that made it hard to cast the protesters as violent.
By the third night, Weiner was fed up with the cops’ incessant beatings. He vented to some fellow marshals that to truly “contest ownership of the streets” one needed only three ingredients: a pile of dirty rags, a tank of gasoline and thin-glassed soda bottles.
As he would later learn, one of the marshals was an undercover cop, leading him and another lesser-known defendant, John Froines, to face the most serious charges: “teaching demonstrators how to construct incendiary devices that would be used in civil disturbances.”
Weiner’s penchant for property destruction briefly resurfaces during our drive to the High & Dry Grill, when I bring up Florida Gov. Ron DeSantis, who grew up in Dunedin and played baseball on a team that made the 1991 Little League World Series.
“What ball field did he grow up playing on?” Weiner asks me. “We should go salt it.” He clarifies that he’s joking, and I kind of believe him.
The main charge applied to the seven derived from the Anti-Riot Act, a law tucked into a 1968 housing bill championed by segregationists to target civil rights leaders. Its signature statute criminalizes traveling over state lines in connection with “inciting or planning a riot.” (In yet another strange echo of our eras, participants in both the Jan. 6 insurrection and the George Floyd protests were charged under the same obscure law.)
The trial, like the protests, was an indignant, sometimes wacky affair. This strange alchemy effectively managed to both expose the role of Chicago police in causing the convention violence and showcase the political zeal of President Richard Nixon’s prosecutors from the Department of Justice. In the end, all seven defendants were acquitted.
The trial was also what Rubin called a “Jewish morality play,” one that exposed an emerging intergenerational shift among Americans Jews that feels newly resonant today. Judge Hoffman was Jewish, as were three lawyers and three defendants: Abbie Hoffman (no relation to the judge), Rubin and Weiner.
Some viewed Judge Hoffman as an over-assimilated Midwestern Jew, including defendant Hoffman, who, in rough Yiddish, derided the judge in court as a “front man for the WASP power elite.” That same day, Rubin deemed him “synonymous with Adolf Hitler.” The wide gulf on display at the trial, which is richly explored in a 2002 academic paper, was largely informed by contrasting feelings and memories of the Holocaust. Another factor was the 1967 Six Day War, which at once fueled Jewish nationalism among older people and, for many younger ones, created newfound consciousness around Palestinian suffering.
Many older Jews at the time supported U.S. involvement in Vietnam on the grounds that criticizing a proxy fight against the Soviet Union was “bad for Israel.” President Johnson, for his part, was offended by anti-war fervor among mostly younger Jews at a time when he was taking new steps to aid Israel.
In the years after the trial, radical political organizations founded by young lefty Jews sprung up, many of them focused on supporting Palestinian rights. Weiner, for his part, defined his Jewishness less around Israel and more around his tribe’s history of radical organizing and political struggle in Europe and America — an identity largely shaped by his mother, Ruth, who steeped him in Marx, Lenin, Trotsky and Studs Terkel. He started a small, short-lived communist collective in Brooklyn that focused on domestic change. After the collective disbanded, he eventually landed at the Anti-Defamation League, then focused chiefly on battling American antisemitism, racism and bigotry, where he stayed for 15 years.
As many older progressive Jews now feel isolated by the fierce protests opposing Israel’s siege of Gaza, Weiner is taking a different approach. His visceral connections to his past remind him that young people are intrinsically uncompromising and naïve, imperfect traits, perhaps, but ones that are critical to activism. Weiner knows that any good movement is clever, forceful and simplistic. “Protest messages have to be relatively short,” he instructs me. “And they generally have to rhyme.” He sees in the current movement blunt messages but also antisemitic ones on the sidelines, a fault, in his eyes, of our current era of diffuse resistance, where “the lack of a publicly recognized leader allows for the emergence of otherwise marginalized and ugly voices.”
After Oct. 7, Weiner considered sending the ADL some money, only to find that they’d gone “a little off the wall” in response to recent demonstrations, including by deeming Jewish-led peace rallies as antisemitic. When, earlier this summer, Wikipedia announced it would start labeling ADL information as “unreliable,” Weiner shot off a furious email to me. “Dumb shits,” he wrote, referring to his former employer. “When they are really, really needed they seem to have let their Israel (not Jewish) agenda overwhelm everything else.”
On our second and final day together, Weiner and I drive west, past the High and Dry Grill out to Honeymoon Island, an ironically beloved spot for a man thrice divorced. (In our time together, and in his book, Weiner is upfront about how his unceasing commitment to politics led to neglect and other failures in his family life.)
On the drive over, we pass through downtown Dunedin, where I spot a patriotic archway on main street. It reads:
★ Defending ★ ★ ★ Freedom ★
Honoring U.S. Military
“I’m glad you live in a town that loves America, but that feels off-brand for you,” I say to Weiner in jest.
“I do love America,” he replies.
“I know,” I say. “I’m just joking.”
“So am I,” he shoots back mischievously.
It’s a perfect bit of snark from a man shaped by a movement steeped in it. But later, Weiner admits he’s leery of me quoting the exchange, worried that it’ll further fortify the perception that anti-war activists hate America. He explains that “the Constitution saved my ass,” adding that his gated community’s pool is frequented by two former special forces operatives, both of whom he likes quite a lot.
Shortly after we arrive at the beach, I spot two dolphins playing, and we watch them for minute, smiling. As small waves lap at our feet, Weiner admits the obvious: that, despite all the natural beauty around him, he finds his mind returning a lot to Chicago.
His memories are bittersweet, recalling real movement power but also a whimpering dissolution, as youthful energy gave away to hardened pragmatism — in this case, the transformation of yippies into yuppies. “Some people stayed in politics, and some people gave up and went for money,” Weiner says. “A good friend of mine turned into a currency trader. He did quite well.”
Still, Weiner was never fully inflexible. Despite his intense opposition to Humphrey in 1968, he voted for him — and urges his younger compatriots to follow suit in November. (He’s toying with producing T-shirts that read “Commies for Kamala,” if anyone’s interested.)
For decades, Weiner’s racked his brain hoping to understand what went wrong after Chicago. “Part of it was age, part of it was drugs, part of it was internal conflicts.” He advises young people to resist becoming hardened by money and practicality, and for his older cohort to rediscover the radicalism of their past — creating the sort of strong, intergenerational bonds that largely eluded the 1968 anti-war movement.
Perhaps the final nail in his movement’s coffin came in 1996, when the DNC Convention first returned to Chicago. It often felt like a sad mutant version of 1968. Richard Daley’s son was mayor, Abbie Hoffman’s son was protesting and some Chicago cops wore shirts reading “We Kicked Your Father’s Ass in ’68 and We’ll Kick Yours in ’96.” Protests were minor, tame and unserious. A major demand by activists was that the U.S. Post Office produce a stamp honoring John Belushi.
I ask for Weiner’s most vivid memory from 1968, and he transports back to the night of August 28, during the so-called Battle of Michigan Avenue. This was the most intense burst of protest, one in which thousands of people, marching peacefully with candles and singing “We Shall Overcome” were stopped and senselessly attacked by law enforcement.
The beatings outside the hall shocked many within, including liberal Connecticut Sen. Abraham Ribicoff, who, at the convention dais, inveighed against “Gestapo tactics in the streets of Chicago.” In response, Mayor Daley stood up angrily on the floor and shouted, “Fuck you, you Jew son of a bitch, you lousy motherfucker, go home!”
At some point during the maelstrom, Weiner peeled off from the crowd, climbed the steps of the Art Institute and lit a cigarette. “It was the only time in my life I thought a revolution in the United States might be possible,” he recalls. “It was nice to have that moment.”
Weiner stopped smoking cigarettes on Jan. 20, 1985 — the day of Ronald Reagan’s second inauguration. He was living in D.C., happened to walk by the capitol and swore, in that moment, to quit cold turkey. “I wanted to outlast him,” he explains.
Not only did Weiner outlast Reagan, he will soon see a spiritual sequel to his proudest political achievement. It’s a new movement now, one characterized by leaderless resistance and a far more diverse population. Today’s young people are burdened by things that Weiner and his peers never needed to worry about, like crushing student debt, disinformation and division sowed via technology, and a heightened sense that an arrest record could ruin one’s future job prospects. The slate of urgent issues has also exploded, thanks both to policy regression on older fronts, like voting rights and abortion, and the emergence of newer battles, like climate change and gun violence.
Still, an emergent movement of young people are out in the streets, fighting for change. Weiner, for his part, remains eager to ring in the revolution. Tucked away in his kitchen drawer is a pack of American Spirits, ready to be smoked when the world makes peace.
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