Far from the thumping, gleaming arena where the carefully choreographed prime-time events of the Democratic National Convention take place, a parallel-universe DNC unfolds in a series of aggressively beige rooms the public never sees.
There’s a trade-show floor the size of an airport hangar, offering everything from Harris-Walz campaign tchotchkes of wildly varying artistic quality to beeswax candles and leather earrings that have zero to do with politics. There’s even a booth lovingly devoted to the history of presidential shoes from Nashville’s own Johnston & Murphy, which has been cladding America’s finest feet since 1850.
Sprawling all around is a massive convention complex where meeting rooms play host to daily training and strategy sessions on the unglamorous essentials by which elections are won and lost: getting out the vote, crafting a message that will grab people, how to boost your campaign with technology or at least not be eaten alive by it. There are dozens each day and most attract only a small audience.
On Wednesday afternoon, there was a workshop called “Spotting and Preventing Infiltration,” hosted by Lauren Windsor, a self-described “advocacy journalist” who has been both a target and practitioner of this dark art. About a dozen people sat in the standard-issue hotel ballroom chairs listening to her spin out a cautionary political whodunit.
The idea of infiltration is to insinuate yourself with a person, event or organization in order to catch someone saying something unguarded that can be recorded and used to expose their partisan team’s hypocrisy or skullduggery. Depending on whom you ask and what they’re trying to justify, this kind of thing wobbles on a knife’s edge between undercover journalism and mafia tactics.
“This, for me, it was very personal, right?” Ms. Windsor said. “I wanted to make sure that no one in the progressive movement went through what I did.”
Democracy Partners, a Democratic consultancy she worked for, got caught up in a scheme in 2016 that amounted to a very tough and public lesson in there being no such thing as a free lunch. The con began with someone offering a $20,000 donation and then soliciting an internship for a niece, who turned out to be a Trojan horse. The fake intern obtained recordings that were publicized by the right-wing provocateur media outlet Project Veritas, and the blast radius reached as far as Hillary Clinton’s presidential campaign.
“‘Oh, I just met you. Can I give you money?’ is about the biggest red flag that ever existed in red flags,” Ms. Windsor told the audience.
She reeled off a long list of other warning signs and soft spots. A bar at a political convention where you’re having a few drinks and feeling loose and happy is a danger zone. Someone who cold-calls you with flattery about your excellent advocacy work and wants to grab coffee is cause for caution. She even warned of honey-pot schemes in which operatives connect with someone through a dating site, then trade on romantic interest to record people saying incriminating or embarrassing things.
She put up a slide showing how tiny cameras could be concealed in a pen or water bottle. She’d been caught once at an National Rifle Association convention, she related with a bit of war-story swagger, when a Texas legislator noticed her talking with her hands and realized her phone was recording.
Ms. Windsor underlined over and over again that people trying to prevent and sniff out infiltrators should pay attention to their Spidey sense.
“I had a gut reaction,” she said. “I should have listened to the gut reaction.”
Ms. Windsor acknowledged that she engages in work some people might view as similar to the conduct she was warning about, but she repeatedly drew distinctions in both target and method.
In her eyes, right-wing infiltrators target low- or mid-level worker bees who may not be politically savvy or well-informed, and “they can then paint the entire party as having those beliefs.” She only goes after bigger game, she said.
“For me, when I go undercover, I’m targeting principals,” she said. “I’m trying to hold somebody to account that’s an elected official that is charged with the public good.”
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Some of her biggest trophies include Supreme Court Justice Samuel Alito and Virginia Governor Glenn Youngkin. She also told her small DNC audience she sticks to undercover work at public or ticketed events that anyone could get access to.
“Having someone go work for your opponent’s campaign should be a bright line,” she said. “Embedding in an organization, having a fiduciary duty, having that kind of obligation and breaching that, I think, is a line that shouldn’t be crossed.”
Democracy Partners sued Project Veritas, and in 2022, a federal jury found the right-wing media group liable for violating wiretapping laws and misrepresentation and fined them $120,000. James O’Keefe, the founder of the group, was fired last year after accusations he’d misspent funds on personal expenses.
It’s clear he still looms large for Ms. Windsor, like a maddening poltergeist. On Wednesday, she mentioned that he’d posted on social media that he had been on the DNC floor.
“It’s an intense thing to think about, all the planning that went into it,” she said of her experience being snared. “And then to think about how it felt on our end to be receiving it.”
Ms. Windsor’s talk was positioned as a technical political operations session, but most of what she spoke about hinged on using human nature against humans.
The most fascinating and messily human bit of the whole thing is how we decide what’s righteous and what’s gross based on who does it and why.