From Militant Activist to Florida Retiree: The THC-Infused Later Years of the Final Chicago 7 Member
Lee Weiner played a pivotal role in the protests of 1968. Today, he finds himself enjoying a smoke in the hometown of Ron DeSantis.
TroibNews 
DUNEDIN, Florida — Lee Weiner presents as a classic Florida retiree, deeply tanned at 84 years of age, often seen in flip flops and frequently enjoying marijuana. His relaxed LinkedIn profile picture shows him grinning shirtless in a hot tub with an ocean backdrop, reflecting his ongoing pursuit of tranquility.
When we meet for the first time on a scorching Tuesday morning in May, he walks me through his daily Daoist routine. We stroll along a path in his gated community, stopping occasionally to appreciate the flowers. Our walk concludes at the pool, where we dip our toes, before heading to one of his preferred spots, the High and Dry Grill, a relaxed palapa offering views of the Gulf of Mexico’s striking blue waters. Although it’s just past 1 p.m., it feels like happy hour. Weiner opts for a “jumbo” margarita, no salt, while I choose a piña colada. As we sip, many of life’s worries seem to fade away.
However, Weiner soon confides in me, a hint of concern in his expression. “I believe we are heading for a very difficult and dark time,” he warns.
The margaritas, ocean breeze, and flowers soothe Weiner, but his underlying concerns remain. He is the last living member of the Chicago Seven, the notorious group of anti-war activists prosecuted for their roles during the tumultuous 1968 Democratic National Convention. Stirring up dissent is ingrained in his identity.
Now, fifty-six years later, the echoes of that time resonate once more, as the Democratic National Convention returns to Chicago amidst intense intraparty strife, largely centered around an increasingly unpopular war.
In 1968, Democrats backed Hubert Humphrey, who stepped in for an unliked incumbent, Lyndon Johnson, who exited late in the game. Richard Nixon represented the Republicans, running on a platform steeped in crime, race, and fear. Both candidates faced strong opposition from a radical protest movement that challenged war, discrimination, and restrictive abortion laws, largely prominent on college campuses where youthful Jewish leaders voiced dissent against their parents’ ideologies. The late Robert F. Kennedy also featured prominently on the ballot. Does this sound familiar?
Weiner stood at the heart of this political whirlwind. He was the only native Chicagoan among the seven, and the youngest member who embodied the spirit of youth, academia, and the city's vital role in the fight for change.
The upcoming protests in Chicago aim to call for an end to U.S. military aid to Israel, with an estimated 25,000 activists preparing to gather in Cook County, which currently has the largest Palestinian community in the U.S. While the immediate impact of these actions may be uncertain, many are likely to label them extreme and ineffective, mirroring critiques from 1968.
Today’s activists often see their predecessors, the baby boomer generation, as having traded in their youthful ideals for corporate roles, comfortable lives, and conservative values. This trajectory famously affected one of the seven, Jerry Rubin, who transitioned from protesting capitalism to becoming a Wall Street entrepreneur.
Some members of the Chicago Seven became intoxicated by their newfound fame, while others faced struggles with addiction. Rennie Davis connected with an Indian guru, while Bobby Seale, the noted Black Panther leader who was briefly in Chicago but charged alongside the seven, has since become a respected writer and speaker. Now 87, Seale couldn't be reached for comment.
Weiner, in contrast to Seale or Rubin, never rose to fame and never desired to. During a press conference amid the trial, he called himself a “technician of the revolution,” lamenting that the case “blew his cover.” He was far from passive, earning an additional contempt charge for correcting Judge Julius Hoffman on the pronunciation of his last name: it’s WHY-ner, not WEE-ner.
Since the trial, Weiner has stayed active and aware of political currents. In contrast to many of his contemporaries, he maintains an optimistic perspective and remains invested in “hopeium,” a term popularized by Gen Z, understanding it as essential fuel for activism.
Weiner’s modest apartment reflects a lack of material gain from his activism, though his gated community boasts socioeconomic diversity, and the gate itself is broken most of the time. His only notable possession from his activism days is a quirky Honda Civic, which he bought with compensation from Netflix for participating in a promotional panel for Aaron Sorkin’s film, “The Trial of the Chicago 7.”
After moving to Florida in 2017, he aspired to step back from activism, hoping to “not be fucking furious all the time.” Yet, he hasn’t fully embraced retirement, having penned a political memoir titled Conspiracy to Riot, which has rekindled connections with young activists through various book talks. “I guess I’m retired,” he remarked to 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 his true intentions are reflected on LinkedIn, where he humorously lists himself as an “aspiring anarcho-commie agitator.”
“I can’t just be in the audience,” he confesses, between inhalations from a weed pen. “It simply isn’t my style.”
Of his various indulgences, Weiner particularly identifies as a “junkie” when it comes to politics. He obsessively keeps up with the news, often starting his mornings in bed with coffee in a Mao Zedong mug, logging into a Wi-Fi network that features a Communist-themed password. (I won’t disclose it in full, but it begins with “RedStar …”)
He is acutely aware that protests, while frequently unpopular in the moment, are historically vindicated over time, maintaining a discerning outlook on Hamas while critically analyzing the U.S.-backed actions in Gaza. “There’s no question — none — that there should be massive demonstrations against the slaughter in Gaza,” he asserts.
Weiner remains a staunch advocate for street protests, even as dissenters claim their impact has waned. While some view protests as divisive, he believes they serve as powerful avenues for change and remedy feelings of isolation. “You’ve got to get out there — to yell at somebody, to hug somebody, to love somebody,” he urges. “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 compounding analogy: “Very few people would disagree that sex is fun and vitally important,” he concludes. “My argument is that politics is the same.”
After a few hours, Weiner and I take in a stunning sunset from his Honda as we drive to a seafood spot called the Lucky Lobster Company. As Weiner enjoys his seafood meal, he recalls the blend of hunger and anxiety he felt while awaiting a verdict in Cook County Jail alongside his co-defendants.
One night, Tom Hayden practiced karate in their holding area, a choice met with amusement from two wise guys who happened to recognize Weiner’s father, Herman, from a painting crew he once worked with. They took an interest in the young Weiner, boasting about their connections to the assistant warden. That night, he insists, he was unexpectedly delivered “a food tray with Cornish game hen and wild rice.”
Among the seven defendants, Weiner was the only one with significant ties to Chicago’s diverse political landscape. He had established connections with mobsters, activists, political figures, and police through his work as a community organizer, where he laid the groundwork for welfare and tenant unions, a legal aid clinic, and a food co-op. His political philosophy also drew heavily from urban academic institutions like Loyola, the University of Chicago, and Northwestern, where he studied revolutions, analyzing case studies ranging from Moses freeing the Israelites to the Bolsheviks.
Weiner perceives the right-wing attacks on higher education today as a backhanded acknowledgment of their value. “Those sorts of spaces are important to play in and be free and to find out what you care about.”
In 1962, while attending the University of Chicago, Weiner committed to the Freedom Rides, but his grandfather intervened, sending him to Israel for a year 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 recounts in his memoir.
This detour ended up being counterproductive, further radicalizing him and preparing him for active participation in the political upheaval at the convention. During his time in Israel, Weiner spent time on a socialist kibbutz, engaged with Jewish and Arab members of the Communist Party, and met Jerry Rubin, who would become both a co-conspirator and co-defendant.
Weiner's connection with Rubin deepened through pilgrimages to New York, where they would indulge in marijuana, attend shows at the Fillmore East, and socialize with prominent figures in the movement, including beat poet Allen Ginsberg and Abbie Hoffman, another co-defendant and leader of the Youth International Party, or Yippies.
Recognizing Weiner’s local connections, Hoffman and Rubin named him a field marshal, tasking him with brokering logistical agreements with police acquaintances and training participants in “active and mobile forms of self-defense,” which humorously translated into rolling up magazines to defend against billy clubs.
One of the remarkable aspects of the 1968 convention was that no one lost their life amid the chaos. It was astonishing how disparate activist groups came together, despite attempts by media and government operatives to fracture them.
“We were often taken in bad faith, seen as traitors to our country — the ‘useful idiots of the North Vietnamese,’” remembers Frank Joyce, an organizer involved in the convention and trial preparations. Abe Peck, a media professor emeritus at Northwestern who documented the trial for a now-defunct radical newspaper, asserts that mass movements face challenges in how they’re framed by media, often focusing on violence over the underlying issues.
The Yippies broke through this media narrative with a series of satirical events, including nominating a pig named Pegasus for president and throwing an “Anti-Birthday Party” for President Johnson. Ginsberg recited Hindu incantations by Lake Michigan, enriching the overall hippie ethos that resisted portraying protesters as violent.
By the convention’s third night, Weiner had reached his breaking point with police brutality. He remarked to fellow marshals that to genuinely “contest ownership of the streets,” three ingredients are necessary: a stack of dirty rags, a tank of gasoline, and thin-glassed soda bottles.
He would soon discover that one of the marshals was an undercover police officer, resulting in him and a lesser-known defendant, John Froines, facing the most severe charges: “teaching demonstrators how to construct incendiary devices that would be used in civil disturbances.”
During our visit to the High & Dry Grill, Weiner jokingly mentions Florida Gov. Ron DeSantis, who grew up in Dunedin and played on a team that reached the 1991 Little League World Series. “What ball field did he grow up playing on? We should go salt it,” he quips, before clarifying that it’s a joke, though I’m not entirely convinced.
The principal charge against the Chicago Seven stemmed from the Anti-Riot Act, a provision integrated into a 1968 housing bill pushed by segregationists aimed at civil rights leaders. The law criminalizes interstate travel related to “inciting or planning a riot.” (Interestingly, participants in both the January 6 insurrection and the George Floyd protests faced charges under this obscure law.)
The trial was a blend of indignation and absurdity, reflecting both the disastrous role of Chicago police in the convention clashes and the political fervor from prosecutors under President Richard Nixon’s administration. Ultimately, all seven defendants were acquitted.
Rubin later described the trial as a “Jewish morality play,” highlighting an emerging generational divide among American Jews that resonates deeply today. Judge Hoffman and three of the attorneys, along with three defendants – Abbie Hoffman, Rubin, and Weiner – were all Jewish.
Some viewed Judge Hoffman as an overly assimilated Midwestern Jew, a sentiment echoed by defendant Hoffman, who derided him in rough Yiddish as a “front man for the WASP power elite.” That day, Rubin labeled him “synonymous with Adolf Hitler.” The stark divide evident during the trial, examined in a 2002 academic paper, was shaped by differing impressions and memories of the Holocaust, alongside the influence of the 1967 Six-Day War, which ignited Jewish nationalism among older generations and gave rise to heightened awareness of Palestinian suffering among many younger individuals.
During this period, many older Jews supported U.S. involvement in Vietnam, arguing that opposing it was detrimental to Israel. President Johnson, for his part, was displeased with the anti-war sentiments among largely younger Jews, especially as he sought new ways to support Israel.
In the years following the trial, radical political groups formed by young progressive Jews emerged, concentrating on advocating for Palestinian rights. Weiner defined his Jewish identity more through the legacy of political struggle and activism than through allegiance to Israel, heavily influenced by his mother, Ruth, who immersed him in the writings of Marx, Lenin, and Trotsky. He briefly started a small communist collective in Brooklyn that focused on national issues. After the group disbanded, he joined the Anti-Defamation League, which concentrated on countering antisemitism, racism, and bigotry in America for 15 years.
As older progressive Jews now feel alienated by the intense protests against Israel’s actions in Gaza, Weiner takes a different stance. He recognizes that youthful activism is marked by uncompromising ideals, an essential quality of effective movements. He understands that every successful movement needs to be clever, forceful, and straightforward. “Protest messages have to be relatively short,” he stresses. “And they generally have to rhyme.” He notes that while today’s protests often convey direct demands, they also contain disturbing antisemitic sentiments, a reflection of a contemporary resistance landscape where “the lack of a publicly recognized leader allows for the emergence of otherwise marginalized and ugly voices.”
After the events of October 7, Weiner contemplated sending the ADL a contribution, only to find themselves “a little off the wall” in their criticisms of recent protests, labeling Jewish-led peace rallies as antisemitic. When Wikipedia announced plans to designate ADL information as “unreliable,” he expressed his frustration in an email: “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.”
During our second and final day together, we drive west past the High and Dry Grill towards Honeymoon Island, a place of irony for someone who has been divorced three times. As we drive through downtown Dunedin, I notice a patriotic archway over Main Street that 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 quip.
“I do love America,” he responds.
“I know,” I reply, “I’m just joking.”
“So am I,” he retorts, a grin spreading across his face.
This playful exchange showcases the spirit his activism embodies. Later, Weiner expresses concern about being quoted on the matter, fearing it might reinforce the stereotype that anti-war activists despise America. He clarifies that “the Constitution saved my ass,” and mentions that his community pool is frequented by two former special forces members whom he respects.
Upon arriving at the beach, we watch dolphins frolic in the distance, sharing smiles as gentle waves lap at our feet. Despite the scenic beauty around him, Weiner admits that his thoughts often draw back to Chicago.
His reflections are bittersweet, recalling the tangible movement power of that era but also the gradual shift to hardened pragmatism that transformed youthful zeal into yuppie culture. “Some people stayed in politics, and some people gave up and went for money,” he reflects, noting the financial success of a close friend who transitioned into currency trading.
Yet, Weiner remains somewhat adaptable. Despite his disdain for Humphrey in 1968, he voted for him — and he encourages younger generations to do the same in upcoming elections. He is even considering creating T-shirts that read “Commies for Kamala,” should there be interest.
Over the years, Weiner has tirelessly pondered what led to the decline of the movement after Chicago. “Part of it was age, part of it was drugs, part of it was internal conflicts,” he observes. He urges young activists to avoid the pitfalls of becoming hardened by money and practicality and encourages older generations to revisit the radical roots of their youth to form strong, intergenerational connections, something that largely evaded the anti-war movement of 1968.
The defining moment for his movement perhaps came in 1996 when the DNC Convention returned to Chicago, all too reminiscent of a muted version of the past. Richard Daley's son was mayor, Abbie Hoffman’s son protested, and some police officers wore shirts proclaiming, “We Kicked Your Father’s Ass in ’68 and We’ll Kick Yours in ’96.” The protests were subdued, lacking the intensity of previous years, with activists demanding a U.S. Post Office stamp in honor of John Belushi.
I ask Weiner for his most vivid memory from 1968, which transports him back to the night of August 28 during the infamous Battle of Michigan Avenue. This was the peak of protest activity, where thousands, carrying candles and singing “We Shall Overcome,” were halted and violently confronted by law enforcement.
The brutal response outside the convention hall shocked observers, including liberal Senator Abraham Ribicoff, who criticized the “Gestapo tactics in the streets of Chicago” from the convention stage. Mayor Daley retaliated angrily, shouting back, “Fuck you, you Jew son of a bitch, you lousy motherfucker, go home!”
In the chaos, Weiner distanced himself from the crowd, climbing the steps of the Art Institute to light a cigarette. “It was the only time in my life I thought a revolution in the United States might be possible,” he reminisces. “It was nice to have that moment.”
Weiner quit smoking cigarettes on January 20, 1985, the day Ronald Reagan began his second term as president. Living in D.C. at the time, he walked past the Capitol and resolved to quit cold turkey, saying, “I wanted to outlast him.”
Not only did Weiner outlive Reagan, but he is also witnessing the rise of a new movement reminiscent of his past. This new generation of young activists is marked by diverse representation and leaderless resistance. Today’s youth face dilemmas that Weiner and his contemporaries never encountered, including overwhelming student debt, disinformation, and the fragmentation facilitated by technology, alongside a keen awareness that having an arrest record could jeopardize job opportunities.
They are confronted with an expanded array of issues, stemming from a regression in policies affecting voting rights and abortion, coupled with new challenges like climate change and gun violence.
Even so, a dedicated new wave of young activists is taking to the streets, battling for change. Weiner remains eager to support their endeavors, with a pack of American Spirits tucked away in his kitchen drawer for when peace is finally realized.
Sophie Wagner contributed to this report for TROIB News
When we meet for the first time on a scorching Tuesday morning in May, he walks me through his daily Daoist routine. We stroll along a path in his gated community, stopping occasionally to appreciate the flowers. Our walk concludes at the pool, where we dip our toes, before heading to one of his preferred spots, the High and Dry Grill, a relaxed palapa offering views of the Gulf of Mexico’s striking blue waters. Although it’s just past 1 p.m., it feels like happy hour. Weiner opts for a “jumbo” margarita, no salt, while I choose a piña colada. As we sip, many of life’s worries seem to fade away.
However, Weiner soon confides in me, a hint of concern in his expression. “I believe we are heading for a very difficult and dark time,” he warns.
The margaritas, ocean breeze, and flowers soothe Weiner, but his underlying concerns remain. He is the last living member of the Chicago Seven, the notorious group of anti-war activists prosecuted for their roles during the tumultuous 1968 Democratic National Convention. Stirring up dissent is ingrained in his identity.
Now, fifty-six years later, the echoes of that time resonate once more, as the Democratic National Convention returns to Chicago amidst intense intraparty strife, largely centered around an increasingly unpopular war.
In 1968, Democrats backed Hubert Humphrey, who stepped in for an unliked incumbent, Lyndon Johnson, who exited late in the game. Richard Nixon represented the Republicans, running on a platform steeped in crime, race, and fear. Both candidates faced strong opposition from a radical protest movement that challenged war, discrimination, and restrictive abortion laws, largely prominent on college campuses where youthful Jewish leaders voiced dissent against their parents’ ideologies. The late Robert F. Kennedy also featured prominently on the ballot. Does this sound familiar?
Weiner stood at the heart of this political whirlwind. He was the only native Chicagoan among the seven, and the youngest member who embodied the spirit of youth, academia, and the city's vital role in the fight for change.
The upcoming protests in Chicago aim to call for an end to U.S. military aid to Israel, with an estimated 25,000 activists preparing to gather in Cook County, which currently has the largest Palestinian community in the U.S. While the immediate impact of these actions may be uncertain, many are likely to label them extreme and ineffective, mirroring critiques from 1968.
Today’s activists often see their predecessors, the baby boomer generation, as having traded in their youthful ideals for corporate roles, comfortable lives, and conservative values. This trajectory famously affected one of the seven, Jerry Rubin, who transitioned from protesting capitalism to becoming a Wall Street entrepreneur.
Some members of the Chicago Seven became intoxicated by their newfound fame, while others faced struggles with addiction. Rennie Davis connected with an Indian guru, while Bobby Seale, the noted Black Panther leader who was briefly in Chicago but charged alongside the seven, has since become a respected writer and speaker. Now 87, Seale couldn't be reached for comment.
Weiner, in contrast to Seale or Rubin, never rose to fame and never desired to. During a press conference amid the trial, he called himself a “technician of the revolution,” lamenting that the case “blew his cover.” He was far from passive, earning an additional contempt charge for correcting Judge Julius Hoffman on the pronunciation of his last name: it’s WHY-ner, not WEE-ner.
Since the trial, Weiner has stayed active and aware of political currents. In contrast to many of his contemporaries, he maintains an optimistic perspective and remains invested in “hopeium,” a term popularized by Gen Z, understanding it as essential fuel for activism.
Weiner’s modest apartment reflects a lack of material gain from his activism, though his gated community boasts socioeconomic diversity, and the gate itself is broken most of the time. His only notable possession from his activism days is a quirky Honda Civic, which he bought with compensation from Netflix for participating in a promotional panel for Aaron Sorkin’s film, “The Trial of the Chicago 7.”
After moving to Florida in 2017, he aspired to step back from activism, hoping to “not be fucking furious all the time.” Yet, he hasn’t fully embraced retirement, having penned a political memoir titled Conspiracy to Riot, which has rekindled connections with young activists through various book talks. “I guess I’m retired,” he remarked to 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 his true intentions are reflected on LinkedIn, where he humorously lists himself as an “aspiring anarcho-commie agitator.”
“I can’t just be in the audience,” he confesses, between inhalations from a weed pen. “It simply isn’t my style.”
Of his various indulgences, Weiner particularly identifies as a “junkie” when it comes to politics. He obsessively keeps up with the news, often starting his mornings in bed with coffee in a Mao Zedong mug, logging into a Wi-Fi network that features a Communist-themed password. (I won’t disclose it in full, but it begins with “RedStar …”)
He is acutely aware that protests, while frequently unpopular in the moment, are historically vindicated over time, maintaining a discerning outlook on Hamas while critically analyzing the U.S.-backed actions in Gaza. “There’s no question — none — that there should be massive demonstrations against the slaughter in Gaza,” he asserts.
Weiner remains a staunch advocate for street protests, even as dissenters claim their impact has waned. While some view protests as divisive, he believes they serve as powerful avenues for change and remedy feelings of isolation. “You’ve got to get out there — to yell at somebody, to hug somebody, to love somebody,” he urges. “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 compounding analogy: “Very few people would disagree that sex is fun and vitally important,” he concludes. “My argument is that politics is the same.”
After a few hours, Weiner and I take in a stunning sunset from his Honda as we drive to a seafood spot called the Lucky Lobster Company. As Weiner enjoys his seafood meal, he recalls the blend of hunger and anxiety he felt while awaiting a verdict in Cook County Jail alongside his co-defendants.
One night, Tom Hayden practiced karate in their holding area, a choice met with amusement from two wise guys who happened to recognize Weiner’s father, Herman, from a painting crew he once worked with. They took an interest in the young Weiner, boasting about their connections to the assistant warden. That night, he insists, he was unexpectedly delivered “a food tray with Cornish game hen and wild rice.”
Among the seven defendants, Weiner was the only one with significant ties to Chicago’s diverse political landscape. He had established connections with mobsters, activists, political figures, and police through his work as a community organizer, where he laid the groundwork for welfare and tenant unions, a legal aid clinic, and a food co-op. His political philosophy also drew heavily from urban academic institutions like Loyola, the University of Chicago, and Northwestern, where he studied revolutions, analyzing case studies ranging from Moses freeing the Israelites to the Bolsheviks.
Weiner perceives the right-wing attacks on higher education today as a backhanded acknowledgment of their value. “Those sorts of spaces are important to play in and be free and to find out what you care about.”
In 1962, while attending the University of Chicago, Weiner committed to the Freedom Rides, but his grandfather intervened, sending him to Israel for a year 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 recounts in his memoir.
This detour ended up being counterproductive, further radicalizing him and preparing him for active participation in the political upheaval at the convention. During his time in Israel, Weiner spent time on a socialist kibbutz, engaged with Jewish and Arab members of the Communist Party, and met Jerry Rubin, who would become both a co-conspirator and co-defendant.
Weiner's connection with Rubin deepened through pilgrimages to New York, where they would indulge in marijuana, attend shows at the Fillmore East, and socialize with prominent figures in the movement, including beat poet Allen Ginsberg and Abbie Hoffman, another co-defendant and leader of the Youth International Party, or Yippies.
Recognizing Weiner’s local connections, Hoffman and Rubin named him a field marshal, tasking him with brokering logistical agreements with police acquaintances and training participants in “active and mobile forms of self-defense,” which humorously translated into rolling up magazines to defend against billy clubs.
One of the remarkable aspects of the 1968 convention was that no one lost their life amid the chaos. It was astonishing how disparate activist groups came together, despite attempts by media and government operatives to fracture them.
“We were often taken in bad faith, seen as traitors to our country — the ‘useful idiots of the North Vietnamese,’” remembers Frank Joyce, an organizer involved in the convention and trial preparations. Abe Peck, a media professor emeritus at Northwestern who documented the trial for a now-defunct radical newspaper, asserts that mass movements face challenges in how they’re framed by media, often focusing on violence over the underlying issues.
The Yippies broke through this media narrative with a series of satirical events, including nominating a pig named Pegasus for president and throwing an “Anti-Birthday Party” for President Johnson. Ginsberg recited Hindu incantations by Lake Michigan, enriching the overall hippie ethos that resisted portraying protesters as violent.
By the convention’s third night, Weiner had reached his breaking point with police brutality. He remarked to fellow marshals that to genuinely “contest ownership of the streets,” three ingredients are necessary: a stack of dirty rags, a tank of gasoline, and thin-glassed soda bottles.
He would soon discover that one of the marshals was an undercover police officer, resulting in him and a lesser-known defendant, John Froines, facing the most severe charges: “teaching demonstrators how to construct incendiary devices that would be used in civil disturbances.”
During our visit to the High & Dry Grill, Weiner jokingly mentions Florida Gov. Ron DeSantis, who grew up in Dunedin and played on a team that reached the 1991 Little League World Series. “What ball field did he grow up playing on? We should go salt it,” he quips, before clarifying that it’s a joke, though I’m not entirely convinced.
The principal charge against the Chicago Seven stemmed from the Anti-Riot Act, a provision integrated into a 1968 housing bill pushed by segregationists aimed at civil rights leaders. The law criminalizes interstate travel related to “inciting or planning a riot.” (Interestingly, participants in both the January 6 insurrection and the George Floyd protests faced charges under this obscure law.)
The trial was a blend of indignation and absurdity, reflecting both the disastrous role of Chicago police in the convention clashes and the political fervor from prosecutors under President Richard Nixon’s administration. Ultimately, all seven defendants were acquitted.
Rubin later described the trial as a “Jewish morality play,” highlighting an emerging generational divide among American Jews that resonates deeply today. Judge Hoffman and three of the attorneys, along with three defendants – Abbie Hoffman, Rubin, and Weiner – were all Jewish.
Some viewed Judge Hoffman as an overly assimilated Midwestern Jew, a sentiment echoed by defendant Hoffman, who derided him in rough Yiddish as a “front man for the WASP power elite.” That day, Rubin labeled him “synonymous with Adolf Hitler.” The stark divide evident during the trial, examined in a 2002 academic paper, was shaped by differing impressions and memories of the Holocaust, alongside the influence of the 1967 Six-Day War, which ignited Jewish nationalism among older generations and gave rise to heightened awareness of Palestinian suffering among many younger individuals.
During this period, many older Jews supported U.S. involvement in Vietnam, arguing that opposing it was detrimental to Israel. President Johnson, for his part, was displeased with the anti-war sentiments among largely younger Jews, especially as he sought new ways to support Israel.
In the years following the trial, radical political groups formed by young progressive Jews emerged, concentrating on advocating for Palestinian rights. Weiner defined his Jewish identity more through the legacy of political struggle and activism than through allegiance to Israel, heavily influenced by his mother, Ruth, who immersed him in the writings of Marx, Lenin, and Trotsky. He briefly started a small communist collective in Brooklyn that focused on national issues. After the group disbanded, he joined the Anti-Defamation League, which concentrated on countering antisemitism, racism, and bigotry in America for 15 years.
As older progressive Jews now feel alienated by the intense protests against Israel’s actions in Gaza, Weiner takes a different stance. He recognizes that youthful activism is marked by uncompromising ideals, an essential quality of effective movements. He understands that every successful movement needs to be clever, forceful, and straightforward. “Protest messages have to be relatively short,” he stresses. “And they generally have to rhyme.” He notes that while today’s protests often convey direct demands, they also contain disturbing antisemitic sentiments, a reflection of a contemporary resistance landscape where “the lack of a publicly recognized leader allows for the emergence of otherwise marginalized and ugly voices.”
After the events of October 7, Weiner contemplated sending the ADL a contribution, only to find themselves “a little off the wall” in their criticisms of recent protests, labeling Jewish-led peace rallies as antisemitic. When Wikipedia announced plans to designate ADL information as “unreliable,” he expressed his frustration in an email: “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.”
During our second and final day together, we drive west past the High and Dry Grill towards Honeymoon Island, a place of irony for someone who has been divorced three times. As we drive through downtown Dunedin, I notice a patriotic archway over Main Street that 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 quip.
“I do love America,” he responds.
“I know,” I reply, “I’m just joking.”
“So am I,” he retorts, a grin spreading across his face.
This playful exchange showcases the spirit his activism embodies. Later, Weiner expresses concern about being quoted on the matter, fearing it might reinforce the stereotype that anti-war activists despise America. He clarifies that “the Constitution saved my ass,” and mentions that his community pool is frequented by two former special forces members whom he respects.
Upon arriving at the beach, we watch dolphins frolic in the distance, sharing smiles as gentle waves lap at our feet. Despite the scenic beauty around him, Weiner admits that his thoughts often draw back to Chicago.
His reflections are bittersweet, recalling the tangible movement power of that era but also the gradual shift to hardened pragmatism that transformed youthful zeal into yuppie culture. “Some people stayed in politics, and some people gave up and went for money,” he reflects, noting the financial success of a close friend who transitioned into currency trading.
Yet, Weiner remains somewhat adaptable. Despite his disdain for Humphrey in 1968, he voted for him — and he encourages younger generations to do the same in upcoming elections. He is even considering creating T-shirts that read “Commies for Kamala,” should there be interest.
Over the years, Weiner has tirelessly pondered what led to the decline of the movement after Chicago. “Part of it was age, part of it was drugs, part of it was internal conflicts,” he observes. He urges young activists to avoid the pitfalls of becoming hardened by money and practicality and encourages older generations to revisit the radical roots of their youth to form strong, intergenerational connections, something that largely evaded the anti-war movement of 1968.
The defining moment for his movement perhaps came in 1996 when the DNC Convention returned to Chicago, all too reminiscent of a muted version of the past. Richard Daley's son was mayor, Abbie Hoffman’s son protested, and some police officers wore shirts proclaiming, “We Kicked Your Father’s Ass in ’68 and We’ll Kick Yours in ’96.” The protests were subdued, lacking the intensity of previous years, with activists demanding a U.S. Post Office stamp in honor of John Belushi.
I ask Weiner for his most vivid memory from 1968, which transports him back to the night of August 28 during the infamous Battle of Michigan Avenue. This was the peak of protest activity, where thousands, carrying candles and singing “We Shall Overcome,” were halted and violently confronted by law enforcement.
The brutal response outside the convention hall shocked observers, including liberal Senator Abraham Ribicoff, who criticized the “Gestapo tactics in the streets of Chicago” from the convention stage. Mayor Daley retaliated angrily, shouting back, “Fuck you, you Jew son of a bitch, you lousy motherfucker, go home!”
In the chaos, Weiner distanced himself from the crowd, climbing the steps of the Art Institute to light a cigarette. “It was the only time in my life I thought a revolution in the United States might be possible,” he reminisces. “It was nice to have that moment.”
Weiner quit smoking cigarettes on January 20, 1985, the day Ronald Reagan began his second term as president. Living in D.C. at the time, he walked past the Capitol and resolved to quit cold turkey, saying, “I wanted to outlast him.”
Not only did Weiner outlive Reagan, but he is also witnessing the rise of a new movement reminiscent of his past. This new generation of young activists is marked by diverse representation and leaderless resistance. Today’s youth face dilemmas that Weiner and his contemporaries never encountered, including overwhelming student debt, disinformation, and the fragmentation facilitated by technology, alongside a keen awareness that having an arrest record could jeopardize job opportunities.
They are confronted with an expanded array of issues, stemming from a regression in policies affecting voting rights and abortion, coupled with new challenges like climate change and gun violence.
Even so, a dedicated new wave of young activists is taking to the streets, battling for change. Weiner remains eager to support their endeavors, with a pack of American Spirits tucked away in his kitchen drawer for when peace is finally realized.
Sophie Wagner contributed to this report for TROIB News
