Dialogs: Talks About Tyranny Triumph at the Chicago Humanities Fest and ACLU Lunch

For “Lakeview Day 2025,” the Chicago Humanities Festival featured two tyranny experts, each for an hour-long interview followed by a brief Q&A, on April 27 at the Athenaeum Theatre. The annual ACLU Illinois luncheon earlier in April featured Sherrilyn Ifill of the NAACP Legal Defense Fund speaking on the currennt onslaught on human rights.

Historian Heather Cox Richardson received a rock-star reception for her talk on her new book, Democracy Awakening: Notes on the State of America. The sold-out crowd was hungry for hope as our country crumbles. While democracy remains “fragile and loved,” she listed some current red flags during this volatile time, including MAGA’s attacks on Congress (notably the gutting of USAID), courts, the economy, business, education and much more.

Richardson agreed that this current chief executive is simply not fit, and then compared the role of the president to the presidency itself, along with power versus institutions. The ideological Project 2025 is spearheaded by Russell Vought, Elon Musk and his teenaged tech bros are infiltrating government and destroying regulations, and sociopathic trolls like advisers Stephen Miller and Kristi Noem are scrambling for control of the presidency themselves.

Adviser Steve Bannon’s edict to “flood the zone” is in full effect because confusion is needed to establish the toxic narrative of this disastrous second term, where there are no remaining guardrails. “The toddlers have the keys to the car,” Richardson said.

Richardson noted some societal touchstones affecting this moment, including that MAGA folks aren’t conservatives but radicals, America has never been a Christian nation, America is currently experiencing the lowest population growth in 80 years, SCOTUS remains a moving target, and that older women remain the mainstays of resistance organizing. Five million people protested against the terrible Trump administration within the first 100 days, she also noted, and pocket Constitutions are regularly selling out (although the ACLU usually has copies).

“This self-created crisis is building by the day,” Richardson said. “Traffic to western shipping ports is down by 50%. Having no taxes, regulations or equality is taking us back to the 1920s, which was bad.” Eviscerating business regulations, the social safety net, infrastructure and civil rights recalls James Baldwin’s predictions about how racism ruins America. “Governments are supposed to push change, not pull back rights,” she added.

She also outlined the GOP’s anti-democracy timeline. Nixon polarized the Dixiecrats, Reagan destroyed benefits like free public college and amped up the racism with ads about Willie Horton, as well as pushing for the narcissistic cruelty of “cowboy individualism,” all leading to this current collapse.

During the audience Q&A, Richardson explained how she wrote this current book. “I hear music in my head while writing,” she said. She also likes to walk and kayak for inspiration. When asked about her Substack newsletter, she said, “Making news easy is hard.”

Timothy Snyder.

In the afternoon, historian Timothy Snyder discussed his new book On Freedom, the follow-up to his frequently sold-out On Tyranny, where the advice “Don’t obey in advance” originated (he penned that brief but vital book in just a few days).

Snyder started with the idea that freedom should not be coupled with “from.” Humans should desire freedom as a condition in which to affirm values, which allows us to do all the other things. He recalled visiting Ukraine and noting that the current war isn’t just about “de-occupation” because that doesn’t make one free. Residents also need to build children’s playgrounds now so that they can enjoy and flourish in this life of freedom.

He also noted that WW2 concentration camps were not really “liberated” since it would take decades for residents to actually be free again. Freedom is not just removal, not just an absence but a presence.

This lecture mirrored his book, which covers the five forms of freedom that we should consider from birth: sovereignty (understanding oneself, the bedrock of freedom), unpredictability (oppressors thrive on predictability, like social media algorithms, which “oppress and nullify”), mobility (rebellion is normal, plus we also need roads and institutions), factuality (truth supports the rule of law especially during this rise of stupidity), and solidarity (collective action and mutual support, not selfish cowboy individualism).

Despite this current darkness, Snyder sees signs of hope. Protests matter because bodies need to connect. “You can’t become an individual alone,” he said. He is encouraged by the students he teaches at various universities and in prisons (some of whom helped him with this book—there is “much talent in the carceral system,” he said).

“We don’t need more efficiency,” Snyder said, “We need other people and that’s why we need the humanities. The arts provide contact that allows access to values.” Most importantly, “freedom has to include empathy.”

Another democracy crusader spoke in Chicago on April 4. NAACP Legal Defense Fund President and Director-Counsel Emeritus Sherrilyn Ifill headlined ACLU Illinois’s annual luncheon “Fighting for a More Perfect Union” at Hilton Chicago. On the 56th anniversary of Dr. Martin Luther King’s assassination, the packed ballroom, including luminaries like state attorney general Kwame Raoul, enthusiastically welcomed the dynamic Ifill, who confessed she has been “grief-stricken” due to the current onslaught on human rights.

Ifill was happy to speak in the city, saying she loves Chicago, loves a luncheon and wants to always be near international waters. She reminded the lunchers that voting rights weren’t fully given to all citizens, notably African-American women, until 1965. We haven’t had these rights for very long, she observed, also noting that the attendees were born and have lived in this post-WW2 sweet spot.

But now, the MAGA Party’s erosion of American institutions is causing a catastrophic societal collapse. “A healthy democracy is undergirded by strong institutions,” she said. “But many have betrayed our trust, including the media, universities, the business community, faith groups and the legal profession. Capitulation benefits the appetites of authoritarians.” She reminded the audience that people are the only important institutions still standing.

She shared that she’s had sleepless nights thinking about the particularly horrifying rounding up of humans to be deported to foreign prisons. “We don’t cut deals to give away due process,” Ifill said. “DEI isn’t eradicated by an executive order. The 1st and 14th amendments aren’t optional.” She launched the 14th Amendment Center for Law & Democracy at Howard University in March to help educate about these crucial protections.

That particular amendment is “the re-founding of our nation, because the word equal was not in the original Constitution, only in the Declaration,” Ifill said. In that original document, slavery was still OK until 1808, she added.

The ACLU created the field of civil rights and civil liberties in 1920, Ifill said, and “we can’t be gaslit. We are a thorn in the side of authoritarianism. We are mission-critical to American democracy because we are not forever set on a path of progress.” She recalled Frederick Douglass’s thought on white supremacy: “the spirit of the traitor is passed from son to son.”

In her closing remarks, Ifill encouraged listeners to continue this work with joy, to take forest baths and listen to Stevie Wonder. “Function with fear, but don’t be paralyzed,” she said.

For more information about how you can get involved with ACLU Illinois, visit their website.

Reserve tickets now for upcoming events at the Chicago Humanities Festival:
May 10: Rebecca Solnit: No Straight Road Takes You There

May 17: Catherine Coleman Flowers: On Activism and Finding Hope

May 18: Jeffrey Seller: Theater Kid

May 28: Jonathan Capehart: Yet Here I Am

June 8: Former Prime Minister of New Zealand Jacinda Ardern in Conversation

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Karin McKie

Karin McKie is a Chicago freelance writer, cultural factotum and activism concierge. She jams econo.