Walter Shapiro, a canny, penetrating and often contrarian political columnist whose career included stints as a presidential speechwriter, stand-up comic, professor, author and, as a college student, congressional candidate, died on Sunday in Manhattan. He was 77.
The cause of his death, in a hospital, was an infection related to his recent treatment for cancer, his wife, the journalist and author Meryl Gordon, said.
Mr. Shapiro’s lifelong passion for politics was piqued in 1962, when he was a high school student in Norwalk, Conn., and his mother gave him a copy of “The Making of the President 1960” by Theodore H. White. The next year, at 16, he took his first airplane flight to attend President John F. Kennedy’s funeral.
He began his career in journalism at Congressional Quarterly and went on to write for Washington Monthly, The Washington Post, Newsweek, Time, USA Today, The New Republic and Esquire. He later wrote for Salon, Yahoo News, Politics Daily and Roll Call.
As a political columnist, Mr. Shapiro was known to pierce the cacophony of snarky commentary, predictive polls and bloviating politicians.
“He was able to convey what was simultaneously ridiculous, ennobling, squalid and necessary,” James Fallows, a former editor of The Atlantic, who started working at Washington Monthly with Mr. Shapiro in 1972, said in an interview.
In 2010, Mr. Shapiro won a Sigma Delta Chi Award from the Society of Professional Journalists for an online column that Politics Daily published under the headline “The Societal Costs of Our Shrill, Hyperactive and Partisan Media Culture.”
At his death he had written dozens of columns on the race between President Biden and former President Donald J. Trump. Their presumptive face-off was the 12th presidential campaign he had covered.
An unabashed Democrat, Mr. Shapiro was known for never pulling punches regardless of his preference. But as with any columnist, especially one publicly committed to a particular candidate, wishful thinking could affect his analysis.
Shortly before Mr. Biden and Mr. Trump debated on June 27, Mr. Shapiro evoked the 2012 encounter between President Barack Obama and Mitt Romney and concluded that “Biden, better than anyone, knows how quickly the effects of a devastating debate can wear off.”
Immediately after that lopsided Biden-Trump exchange, though, Mr. Shapiro wrote that Mr. Biden “should ask himself the blunt question: ‘Can I save American democracy by beating Trump?’ Judging from his performance in the historically early debate that Biden sought, the answer, sadly, is ‘no.’”
Mr. Shapiro died on the day Mr. Biden announced that he was withdrawing from the 2024 campaign, leading the political commentator and author Joe Klein to write in his newsletter, Sanity Clause, “It is so ironic that he passed away in the midst of perhaps the most significant political drama of our lifetimes.”
In covering campaigns, Mr. Shapiro drew on his own personal political history.
He was still a student at the University of Michigan in 1970 when he finished second in the Democratic primary for a House seat representing a newly redrawn district that included the university’s campus in Ann Arbor. “I drove in a borrowed Volvo, made in Sweden and not Detroit, to my pro forma endorsement interview with the United Auto Workers,” he later wrote in Roll Call.
But the experience informed his later work as a political writer. “As a campaign reporter,” he wrote, “my long-ago political career has given me empathy for candidates, especially the long-shot dreamers, who are out there with a shoeshine and a smile propelled by an abiding faith in American democracy. Too much cynicism in covering politics is a crippling malady for reporters and pundits.”
Walter Elliot Shapiro, a grandson of a Jewish peddler from Prussia, was born on Feb. 16, 1947, in Manhattan to Salem Shapiro, a city planner, and Edith (Herwitz) Shapiro. The family moved to Connecticut, where Walter attended Brien McMahon High School in Norwalk.
Earlier this year, in a warning to voters flirting with third-party candidates in the 2024 election, Mr. Shapiro recalled that he “squandered” his first presidential vote in 1968, when he was in college, by casting it for Eldridge Cleaver, the Black Panther leader who was running on the Peace and Freedom Party ticket.
“What haunts me with surprising frequency these days was my jejune refusal to back Vice President Hubert Humphrey in 1968 out of misplaced antiwar passions,” he wrote in The New Republic.
After earning a bachelor’s degree in history from Michigan in 1970, Mr. Shapiro studied for a master’s degree in European history there.
He had so many jobs that he often likened himself to a Civil War general whose horse kept being shot out from under him. He worked on Jimmy Carter’s 1976 presidential campaign, then as press secretary to Ray Marshall, the labor secretary. He went on to write speeches for Mr. Carter during his presidency (and, he recalled gratefully, was never admonished for once confusing William Henry Harrison with his grandson Benjamin in a Carter address). He was also an adjunct professor at Yale and a fellow at the Brennan Center for Justice in Manhattan, a nonpartisan research group.
Mr. Shapiro moved beyond the Beltway, from Washington to New York, in 1983. In addition to his wife, he is survived by his sister, Amy Shapiro.
As an avocation, Mr. Shapiro performed stand-up comedy in Washington and New York. In 1998, The Times of London called him “one of Manhattan’s leading political satirists.”
He punctuated his political coverage with witty asides. In 1992, Bill Clinton was trailing President George Bush and Ross Perot when he was booked on “The Arsenio Hall Show.” Donning dark glasses and playing “Heartbreak Hotel” on the saxophone, Mr. Clinton solidified his support with young urban audiences. Mr. Shapiro wrote in Time, “Bill Clinton may have discovered the formula to revive his stalled campaign: Exploit his sax appeal.”
In addition to his columns, Mr. Shapiro wrote two books: “One-Car Caravan: On the Road With the 2004 Democrats Before America Tunes In” (2003) and “Hustling Hitler: The Jewish Vaudevillian Who Fooled the Führer” (2016), about his grifter great-uncle who may, or may not, have fooled the Nazis into buying what they thought was a cargo of nickel — and of whom Mr. Shapiro admitted he was unduly proud.
“In my Walter Mitty moments,” Mr. Shapiro wrote in “Hustling Hitler,” “I like to think that the music hall programs, the abandoned vaudeville troupes, the betting slips, the pawnshop tickets, the kited checks, the phony business cards, the outlandish schemes, and the zest for living the self-invented life are all entwined with my own DNA.”
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