Former New York City politician Andrew Stein says his decades-long bond with the late Gloria Steinem, born in the tear gas and turmoil of the 1968 Democratic convention, collapsed the moment he backed Donald Trump.
Steinem died last week at 92. Within days, Stein, now 81, shared a story that reads like a parable of American political life: two people drawn together by a shared obsession with politics, pulled apart when that obsession led them to opposite conclusions. Stein recounted the full arc, from a bold convention-floor pickup to a final, bitter phone call, in terms that were blunt and affectionate at the same time.
The setting was Chicago's International Amphitheatre, August 1968. The Democratic National Convention had devolved into something closer to a siege. Stein, then the youngest delegate in attendance, described the scene outside the hall in stark terms.
"Tanks and tear gas and bayonets. You'd have to have been there to realize this was America."
Security locked the convention floor to credentialed delegates only. No press, no visitors, no exceptions. That restriction set the stage for an unlikely transaction.
Stein recalled a young woman approaching him amid the chaos and asking to borrow his delegate credentials for twenty minutes, just long enough to get onto the floor. He did not know who she was.
His counter-offer was immediate. As Stein tells it:
"No. But you can borrow them for the rest of the day if you have dinner with me tonight."
She agreed. "OK, it's a deal," Stein recalled her saying. It was only after the exchange that Abbie Hoffman, the radical activist who was a fixture of the 1968 protest scene, clued Stein in. "Dude, you just picked up Gloria Steinem!" Hoffman told him, at least in Stein's telling.
Steinem at the time was working as a journalist and political writer, years before she founded Ms. Magazine and became one of the most recognizable figures in the feminist movement. A Chicago Tribune writer later described her performance on local columnist Irv Kupcinet's television show that same convention week: Steinem "waded right in and quickly dispatched the city and police spokesmen with steely determination," the writer recalled, calling her "one of the ablest and gutsiest reporters I had ever seen."
That dinner led to more. "We had dinner. We ended up having a little affair for three, four or five months," Stein said. Steinem lived at 118 East 73rd Street in New York City, an address she kept, Stein noted, until the day she died.
The romance faded. The friendship did not, at least not right away. Stein described a bond that survived the end of the affair and stretched across decades, sustained by long phone conversations late at night.
"We were both so into politics. She got more liberal and I got more conservative. [We] gradually went to a friendship, but we would talk on the phone for decades late at night. We would talk, even after there was no romantic relationship."
Stein's own career took a different trajectory from Steinem's. He served as Manhattan Borough President and New York City Council president, ran for mayor and for the U.S. Senate, and eventually became an ally of Donald Trump, a political migration that would have been unremarkable in an earlier era but became unforgivable in the age of Trump.
Trump himself has continued to shape the political landscape in ways that divide old alliances and create new ones. His influence on the Republican Party has prompted ongoing debate about his future role in American governance.
Stein and Steinem last shared a meal roughly a decade ago, by Stein's account. But the phone calls continued, until 2016.
That year, Stein published an op-ed in the Wall Street Journal under the headline "Party Loyalty Can't Make Me Vote for Clinton." The piece amounted to a public endorsement of Trump over Hillary Clinton, a declaration that, for a lifelong Democrat, carried the weight of a formal defection.
Steinem called him. Stein recalled her words plainly: "How can you support someone like that?"
His answer was just as plain. "I think he's a better president than Hillary," Stein told her.
"And that was the last time I spoke to her."
The political divide that ended their friendship was not unique to them. Across the country, the 2016 election fractured relationships that had survived every prior disagreement. But few of those fractures stretched back fifty years, or began with borrowed credentials on a convention floor ringed by National Guard troops.
The broader pattern of political splits within institutions and alliances has only deepened since then. Even within the Republican Party, disagreements over judicial appointments and legal strategy have tested loyalties that once seemed secure.
Stein did not pretend the break was painless. He spoke of Steinem with open warmth even while acknowledging the gulf that separated them.
"She was a sweet tender person, but she was a real liberal, the vibe, it divides you."
He added: "She was a sweetheart... I loved her. She was a wonderful woman."
That combination, genuine affection and unbridgeable political distance, is the core of the story. Stein does not blame Steinem for cutting him off. He does not apologize for backing Trump. He simply describes what happened when two people who once shared everything arrived at a question neither could finesse.
Trump's own legal and personal battles have continued to create headlines, including recent Supreme Court decisions that have kept his name at the center of national debate.
Stein summed up the end of the friendship in six words: "The politics got too much."
And his administration's ambitious agenda, from policy to physical transformation of the White House itself, has driven high-profile court fights that underscore how thoroughly Trump reshaped the terms of American political loyalty.
Fifty-eight years from a borrowed credential to a severed friendship. If you want to understand what politics has done to this country, that timeline tells you more than any poll.
