In June 2025, a rainy Tuesday night in Hartford felt more like a history seminar than a political rally. Former President Barack Obama sat down with historian Heather Cox Richardson at the Bushnell Theater, and honestly, the vibe was different than his usual high-energy stump speeches. It wasn't about soundbites. It was about the "long game" of democracy, and if you've been following Richardson’s Letters from an American, you know she isn’t one for fluff.
They talked for nearly 90 minutes. Obama, looking comfortable but sounding undeniably urgent, didn't even mention Donald Trump by name once. Not once. Instead, he and Richardson dissected the "frightening flirtation with autocracy" currently gripping global politics. It was a meeting of the "Hope" guy and the woman who explains exactly how our history is repeating itself.
The Problem With "Maximalist" Politics
Richardson kicked things off by asking about the tension in Obama’s own memoir, A Promised Land. She pushed him on the idea of working within a system that often feels broken. Obama’s take? We’ve become too cynical. He argued that a big, messy country like the United States can't function if everyone demands "maximalist outcomes" all the time.
Basically, if you want 100% of what you want right now, you’re going to be disappointed. He called it a "game of addition, not subtraction." This is a tough pill to swallow for activists on the ground, but Obama insisted that progress only sticks when you find common ground with people who agree with you on maybe 20% of things.
Why the "Better Angels" Are Hiding
Richardson, ever the historian, brought up the Edmund Pettus Bridge. She compared the current political climate to the era of John Lewis and the Civil Rights movement. Obama’s response was blunt. He noted that for a long time, relatively privileged people in America could be "progressive and socially conscious" without actually paying a price.
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"You could still make a lot of money," he said. "You could still hang out in Aspen and Milan... and still think of yourself as a progressive."
Now? The price is higher. Commitments are being tested. He pointed to the way donors might flee universities or law firms might see billings drop if they take a stand. It’s not Nelson Mandela-level sacrifice—he joked about not being able to remodel a kitchen in the Hamptons—but it’s a real test of character that many aren't passing.
Facts vs. Fiction: The Substack Connection
One of the most interesting moments was when Obama praised Richardson’s newsletter. He liked it for being "clear-eyed" about what is fact and what is fiction. This matters because, as he pointed out, a huge chunk of the electorate currently lives in a reality where the 2020 election was stolen—a claim he flatly called "dangerous."
He used his own inauguration as a lighthearted example. He joked that his inauguration had more people than Trump's, then quickly added that he doesn't actually care about the crowd size, but he cares that people lie about the facts of it. When one major party pretends facts aren't real, the guardrails of democracy start to crumble.
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The Orbán Warning
Obama was surprisingly sharp when discussing foreign "pretenders." He lumped Russia’s Vladimir Putin and Hungary’s Viktor Orbán together. He warned that we are "dangerously close" to normalizing behavior that is more consistent with autocracies than with American democracy.
Democracy isn't self-executing. It requires people in the Justice Department, judges, and regular citizens to actually take their oaths seriously. Richardson noted that five days before the event, she had released a video titled "Now is the Time to Take Sides," sparked by the physical removal of Senator Alex Padilla from a press conference. The stakes felt incredibly local and incredibly global all at once.
Can We Still Be Optimists?
To close the night, Richardson asked the million-dollar question: How do young people stay optimistic?
"I'm still the hope guy," Obama replied.
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He told the audience that it's okay—and actually necessary—to be impatient with injustice. There is such a thing as "healthy outrage." But he warned against staying in digital cocoons. Real change happens when you meet people face-to-face and those "better angels" Lincoln talked about actually have a chance to show up.
Actionable Insights for the "Office of Citizen"
If you’re feeling the "democracy fatigue" that Richardson and Obama discussed, here are a few ways to apply their conversation to your own life:
- Audit Your Information: Follow sources that prioritize primary documents and historical context over emotional headlines. Obama specifically cited Richardson's Letters from an American as a model for this.
- Practice "Addition": Identify one local issue where you can work with someone you disagree with politically. Focus on the 20% of shared goals rather than the 80% of conflict.
- Support the Guardrails: Pay attention to local elections for "boring" offices—election board members, judges, and secretaries of state. These are the people who hold the line when the system is tested.
- Engage Offline: Move away from the "outrage machine" of social media and join a physical community group or a local board. As Obama put it, democracy works best when we start recognizing ourselves in each other.
The Hartford talk proved that while the "Hope" era might be in the rearview mirror, the work of maintaining a liberal democracy is a daily, unglamorous grind. It isn't about finding a savior; it’s about the "office of citizen" doing the heavy lifting.