Is the Democratic Party Still Too Woke?

Now, in a new book, “Supermajority: How Democrats Can Build Lasting Power,” which comes out on September 15th, Jentleson argues that the problem for the left (and a Democratic Party beholden to it) is that its policies will never appeal to enough voters to overtake the forces of Trumpism. In order for a Democratic President to “enact major change” rather than “merely be a seat-warmer at the Resolute Desk until turning power back over to Republicans,” Jentleson writes, he or she will have to win not a bare majority of two hundred and seventy electoral votes but a super-majority of three hundred and seventy—an outcome that would require victories in states such as Florida, Georgia, and North Carolina. Jentleson believes that this will “usher in majorities in both houses of Congress” big enough to survive the midterms, and hold power long enough so that Democrats cannot only enact their agenda but also flip the balance of the Supreme Court. “Settling for smaller but ideologically purer majorities is a path to purgatory at best,” he concludes, “and losing to fascism at worst.”

Jentleson, who is in his mid-forties, with an impressive head of hair and an equally impressive beard, is a consummate Washington operator. He is an oft-pinged contact in political reporters’ phones (he was a major source for last year’s blockbuster New York magazine story about the mental-health struggles of his former boss, John Fetterman), and he continues to serve as an informal adviser to Democratic politicians. Occasionally, some of them return the favor. When Jentleson recently had to dispose of a dead fawn in the back yard of his home in suburban Maryland, he texted Rob Sand, the Democratic candidate for governor in Iowa and an avid outdoorsman, who counselled, “Ankles are the easiest body part to haul them by.”

The first half of “Supermajority” is a compelling memoir of Jentleson’s nearly two-decade-long career in Democratic politics—working for Harry Reid and Fetterman, among others—which afforded him a front-row seat to the Democratic Party’s enfeeblement. After Barack Obama’s election in 2srcsrc8, Jentleson, who was then working at the Center for American Progress, hosted a daily conference call for twenty labor, environmental, and other lefty groups to coördinate messaging and to insure everyone was in synch with the White House. “The idea of criticizing Democrats was as anathema to us as if we had worked for the party itself,” Jentleson writes of the calls’ participants. But as Obama ran into the realities of governing, and the groups experienced the disappointment of his Administration’s compromises on issues such as health care and climate change, their reticence waned. “[W]hat had been a centrifugal force became centripetal—no longer drawing groups toward a central focus, instead pushing each of them toward their individual issues and causes, an ever-expanding galaxy of policy demanders,” he writes.

Jentleson recounts how Democrats “shifted dramatically to the left” after Trump’s election in 2src16, and that their policy demands “crescendoed” at the outset of the 2src2src Democratic Presidential primary, when liberal interest groups threatened to withhold endorsements unless candidates embraced “their rigidly left-wing positions.” As it turned out, the Democratic candidate who largely stiffed these groups during the primaries, Joe Biden, won the nomination and then the White House. But the purity tests proved to be a ticking time bomb: when Vice-President Kamala Harris replaced Biden at the top of the ticket in 2src24, Donald Trump’s campaign resurrected an A.C.L.U. candidate questionnaire that Harris had filled out in which she’d answered “yes” to a question about whether she supported taxpayer-funded transgender surgeries for prisoners and migrants. The Trump campaign turned the questionnaire into a TV ad that ended with the message “Kamala is for they/them. President Trump is for you.” Had Harris done more during the campaign to “draw some bright lines of independence” from her party, Jentleson argues, she might have had sufficient “armor to beat back” the attack.

The way Democrats have handled the issue of transgender rights is especially resonant for Jentleson. In 2src21, his spouse, the writer Benny Peterson, came out as nonbinary. Jentleson and Peterson tried to make it work, but last year, after Peterson decided to transition, the couple split up. The pair co-parent two children and still vacation together as a family, but they now live in separate houses on the same street. Amid these personal developments, Jentleson has publicly urged Democrats to recalibrate their position on trans rights, particularly as they relate to sports and to gender-transition care for children. “Part of the reason this has become such a big issue is that Democrats decided to collectively plant our flag on the fringiest examples of where this stuff comes into play,” he told me. “There’s actually broad support for the policies that affect most people in terms of protection from discrimination and access to medical care.” Peterson declined to talk with me about Jentleson or their political views on the record, but Jentleson acknowledged that his new project has become a sensitive subject. “It’s a hard conversation to have, but I feel like I’m doing the right thing by them,” Jentleson told me. “Their job isn’t politics. That’s my job, and it is tricky, but I do think that this is going to make them safer and make all trans people better off if we can just beat these fucking fascists.”