Happy Hanukkah and Giving Tuesday.

A core theme of my coverage is that you’ll find the same tensions, the same characters, the same obsequiousness and the same egos in the development office of the Red Cross as you will on the finance staff at the Democratic Senatorial Campaign Committee. It doesn’t make to sense to cover philanthropy and politics separately. Philanthropy is politics, and politics is philanthropy.

So today, let's talk candidly about the blurred lines. The full inside story is only available to Puck subscribers. Not a member? Sign up here, or gift a membership to a friend who works in the field.

Inside the Dems’ Dark Money Machine

Neither party's functionaries admit it, but the line between philanthropy and politics has been obliterated. The upshot is that even more money is moving into the shadows.

One of the more piquant aspects of my career has been watching the people I cover today learn from the people I covered years ago. It can sometimes feel like you’re seeing a new cast perform an original play with a novel spin on the script, like Mark Zuckerberg reinventing himself as a philanthropist in the mold of Bill Gates, or today’s tech leaders lobbying Washington in the mold of John Doerr. Over the last few weeks, however, I’ve felt some deja vu over a more bipartisan phenomenon, studying with amazement how the mega-donors of the left have perfected the playbook authored by their rivals on the right.

Before moving to Silicon Valley, I spent a few years in Houston and Washington reporting on the machinations of conservative mega-donors, like the billionaires Sheldon Adelson, Bob Mercer and, of course, Charles and David Koch. I’d attend their donor confabs—getting tossed by security for sneaking around the halls at Adelson’s Venetian, schmoozing the establishment set over drinks at Mitt Romney’s ideas summits at a Park City chalet, or hunting for leaks at the Kochs’ annual “seminar” at the idyllic Broadmoor in Colorado Springs. The power of these G.O.P. fundraising networks resided in their sophisticated mastery of the tax code, and their gumption in exploiting it. At the center of the Kochs’ influence machine, after all, was their spider web of almost entirely tax-exempt nonprofits—most expressly political, others as nominally do-goodery as a Rotary Club—that allowed donors to shield their identities while funneling billions of dollars over the decades into everything from promoting tax cuts to downplaying climate change.

Meanwhile, Democrats were wrestling with purity politics that today seem almost quaint. During the 2012 presidential election, the first after the Citizens United decision ushered in a new era of mega-donordom, Barack Obama’s team hemmed and hawed over whether to embrace Priorities USA, the super PAC that eventually buried Romney in millions of negative ads. Liberals consoled themselves with the notion that they could not “unilaterally disarm.” Four years later, the debate over big-money politics had largely receded: John Podesta’s hacked correspondence is a fascinating window into just how savvily Hillary Clinton played that game. By the time that 2020 rolled around, Democrats had mastered the new terrain that the right had excavated, injecting their outside groups with steroids even as they bemoaned the coarseness of the Swift Boat era.

All that has been obvious for some time. But I was nevertheless rendered slack-jawed over the past few weeks as new tax returns were published, revealing the incredible growth of Democratic dark-money networks, which took in hundreds of millions—possibly billions—of dollars during the 2020 campaign...

FOUR STORIES WE'RE TALKING ABOUT