In my many years working in politics, I have attended hundreds, if not thousands, of fundraising events. A fundraising trip is a tour of the twin plagues of economic inequality and money in politics. These events are held at huge brownstones on the Upper East Side, giant tech-funded mansions in Silicon Valley, ancestral estates in the Berkshires, and homes overlooking the ocean in Malibu and the Hamptons. Each of these venues would be worthy of its own episode of Million Dollar Listing. However, I rarely toured these totems to wealth (inherited and “earned”). At these hoity-toity events in people’s homes, there is usually a room for the politician’s staff. These “hold rooms,” often servants’ quarters or pool houses, are removed from the action. In New York City apartments, they are often spare bedrooms or kids’ rooms with custom bunk beds. During presidential events, the hold room would be crowded with military aides, doctors, and the traveling government-in-waiting, in case a crisis broke out while the president was away from the White House.
At these events, senior campaign staff are encouraged to mix and mingle with the guests. There is only so much of the candidate to go around, and the organizers want the donors to feel they’ve gotten their money’s worth of access. But, much to the chagrin of the fundraising staff for the Democratic National Committee and the Obama campaign, I did everything to avoid the mix-and-mingle obligation. As soon as I arrived with President Barack Obama or the myriad other politicians whom I’ve traveled with over the years, I would head directly to the hold room to hide out. The primary impetus for my self-imposed exile was my aversion to small talk. But I also hid to avoid something I called “the Question,” an inevitable feature of any conversation with any group of Democratic donors.
It didn’t matter if Democrats had won or lost the most recent election. The Question comes in many forms, but it always boils down to some version of: Why do Democrats suck at messaging? The Question was usually, but not always, asked politely. Sometimes it came with a series of ideas. Politics is one of those endeavors where everyone thinks they are qualiﬁed to have an opinion. And the people successful enough to write checks big enough to attend these events are generally not the sort of people who experience self-doubt.
For much of my time in the White House, I was anonymous in face and name to all but the most attuned political observers. But in a crowd of well-heeled donors, I had all the markings of a staffer: a little too young, a bit haggard, with the dark circles that are imprinted under the eyes after a year of working White House hours.
Eventually, as I stood in a corner hoping the server with the pigs in a blanket would come by, someone would invariably wander over to me and ask, “Are you on the White House Staff?”
“What do you do?”
“I’m President Obama’s communications director.”
“Oh, good. I was hoping to run into you. I have some thoughts…”
And we were off to the races.
I never had a great answer for them—or, at least, I never had an answer they found satisfactory. And their “thoughts” usually amounted to their pretending that their experience making a fortune selling mail-order underwear, betting against the housing market, or producing a hit sitcom made them qualiﬁed to do my job.
Political donors are not the only ones obsessed with “the Question.” Pundits and the political press are constantly haranguing Democrats for their messaging mistakes. One liberal writer of several well-reviewed presidential histories called me often during Obama’s ﬁrst term to lecture me on why Obama didn’t yet have a version of FDR’s New Deal or LBJ’s Great Society. The subtext of these conversations was that great slogans make great presidents. Much of Progressive Twitter is ﬁlled with lamentations about some failure or missed messaging opportunity. There was a running joke in the Obama White House that you needed a master’s in economics to discuss economic policy and a doctorate in public health to offer health care ideas, but everyone believed that reading the newspaper made them qualiﬁed to opine on messaging strategy.
My own fragile self-esteem and awkwardness aside, I hate trying to answer the Question. Not only are there no easy answers, it’s the wrong question.
Republicans are winning the message war, but not for the reasons these donors, the media, or 90% of the folks on Twitter believe. And there are steps we must take to change this very annoying dynamic.
In this more mature, less defensive phase of my life, I’ve stopped hiding from the Question (and the questioners). Instead, I’ve found a more accessible, equally dissatisfying way to address the actual problem without absolving the party (or myself) of mistakes and missed opportunities. But before I get to the Democrats, I am going to use authorial privilege to talk about why Republicans suck at messaging.
When donors, activists, and media folks ask why Democrats suck at messaging, they are really asking why Republicans are so much better at it.
There is an old saying in Washington: “The only people who believe Republican talking points are Democrats.” This inherent sense that Republicans are better at politics than Democrats has survived as a feature of my party’s psychology for decades. Democrats love to imbue our opposition with strategic evil genius. Roger Ailes, Lee Atwater, and Karl Rove are famous mostly because Democrats have hyperinﬂated their roles to explain away our losses.
There is no doubt Republicans are winning the messaging war, but are they winning because they are better messengers?
Democrats love to complain about the messaging chops of their congressional leadership team, but have you watched the Republicans? During every appearance, Kevin McCarthy looks like he just woke up from a nap and can’t ﬁgure out where he is or what he is doing. Mitch McConnell, one of the worst communicators in modern political history, sounds like he is reading The Almanac of American Politics with a mouthful of marbles. And no one exempliﬁes the adage of “less is more” more than Ted Cruz, an amalgamation of the ﬁve most annoying people you went to high school with. Arkansas senator Tom Cotton makes Jared Kushner look like a magnetic personality. Turn on Fox News, and you’ll ﬁnd a parade of awkward, angry white men doing bad impressions of Donald Trump. Even Trump, the supposed master media manipulator, has the discipline and strategic thinking of a coked-up Tasmanian devil. Just look at his Twitter feed from the end of the 2020 campaign. Instead of using his biggest platform to drive home a positive argument for his reelection and a negative message against Joe Biden, Trump engaged in a scattershot Festivus-style airing of grievances against members of his own party, the media, and random celebrities.
This dynamic is in part why the founders of the Lincoln Project became huge celebrities among the Resistance Twitter/MSNBC crowd. The former political consultants, all Republican Never Trumpers, were able to siphon tens of millions of dollars from willing progressives hoping to sample some of that Republican messaging magic. The Lincoln Project was touted as tougher, faster, and smarter than those mealy-mouthed Democratic ad makers whom Democrats love to hate. Though, at no point have folks asked, “If the Lincoln Project is so good, why did so many of its founders keep losing presidential elections to Democrats?” Nor has anyone stopped to wonder if an ad that appealed to highly engaged, very online liberals in California or New York would really be effective with disenchanted Republicans in Ohio and Iowa.
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