15 DAYS AGO • 6 MIN READ

What we can learn from Trump and Mamdani

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How We Win

Every few weeks, I’ll share my thoughts on movement strategy, politics, and the fight ahead.

My thoughts on movement strategy, politics, and the fight ahead.

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Well, friends, it's been a good week. We saw wins at the ballot box in many places across the country, from New Jersey to Virginia to Detroit. And of course, here in NYC, Zohran Mamdani's decisive victory is a massive win for progressives— not just here but nationwide. Over the next few weeks, there will be all kinds of analyses of why he won, as many try to replicate his success and others try to prevent it from happening again. But I wanted to offer a few of my own thoughts.

Communication Is the Work

Obviously Mamdani has many skills, but perhaps his most remarkable one is his ability to effectively communicate – as a politician, as an organizer, and as an outsider. For someone who isn’t part of a political dynasty and didn’t have immediate access to deep pockets in the initial stages of his campaign, his communication skills were crucial. Much of the groundwork for this victory was paved in the years before his race, and reforms like public financing and ranked choice voting have helped provide fuel to the powerful infrastructure of the Working Families Party, DSA, and others. With that foundation, and a candidate as uniquely talented as Mamdani, what was once a longshot suddenly became reality.

Now, as the mayor of New York - the ultimate insider - he will have all the power of that office to communicate at an even higher level. He now has the tools to both get things done and to sell what he’s done. The question is: will he do it?

It’s not just a question for him, but for progressives across the country - those in office, those that won Tuesday night, and those that may run in the future. That’s the real challenge ahead for those of us working for progress. They have to understand that communication isn’t secondary. Communication is the work itself.

Learning from Trump’s Playbook

No one understands this better than Donald Trump. In many ways, he’s the most effective communicator to occupy the White House in our lifetime. He’s weaponized every possible communication channel to defend the indefensible. From ICE ads to Social Security emails to the White House website, his administration prioritizes messaging above all else, constantly driving home the framework and perspective they want Americans to embrace.

If you’ve seen some of the recent Department of Labor instagram posts, for example, you know what I mean. The 1940s-style posters with white faces and slogans like “Restore the American Dream” and “Americans First.” They’re not just nostalgic; they’re revisionist — reframing segregation and exclusion as patriotic virtue. They’re telling a story about who belongs and who doesn’t.

When Progressives Go Quiet

Meanwhile, many on our side seem to have abdicated the responsibility to communicate effectively. Biden once admitted that he was “stupid” not to sign his name on the pandemic relief checks, which would have allowed people to connect their additional income to his administration. And it was stupid. Because it’s not just good enough to do the thing. You have to shape the way people see it. Communication — who tells what story to which audience — shapes what people believe is possible.

Trump would have never made the mistake of not signing the checks. He knows how to sell himself, frame his accomplishments, and even sell what people don’t want to buy. Right now, he’s selling cuts to SNAP, and doing it with a chorus of politicians backing him, while a sea of social media influencers proclaim that Black people don’t deserve it. As I talked about in my last newsletter, supporters of the administration are selling a racist depiction of SNAP recipients — weaponizing racism to gain support for policies that hurt everyone. Every organ of his communication machine — state agencies, social media, cable news — is reinforcing that message. It’s relentless.

That’s the bar now for Mamdani and for every progressive in office. To use all the powers of communication available to them — including those their predecessors never thought to use. That’s how we counter the consolidation of media and message that the right has mastered, as I wrote about a few weeks ago. We can’t keep governing like communication is an afterthought. We can’t leave anything on the table.

Real communication isn’t just about contact or visibility. It’s about connection – we are giving people something they need. Speaking to small groups of people in ways that build up to large groups of people getting aligned. Mamdani’s campaign executed this strategy almost flawlessly. Now the hope is he can do the same while in office.

A Few Thoughts on Boots

Which brings me to another, seemingly unrelated, thing I’ve been thinking about… The Netflix show Boots.

If you haven’t seen it, Boots is part coming-of-age story, part queer dramedy, part military lionization (and critique), and wildly popular (especially with queer audiences). It’s a show that speaks directly to specific experiences…queer people, yes, but beyond that, too.

And there’s one small scene that’s stayed with me. It’s the first day of boot camp. A young Black recruit, newly shaved, hesitates with a razor. A white recruit mocks him for having sensitive skin. Then an older Black drill sergeant walks over and silently sets down a blue can of Magic Shave.

Like many black rituals and traditions, Magic Shave is a strange and beautiful kind of inheritance. Back then, it was a powder you mixed with water, sharp enough to burn your fingers, gentle enough to save you from the daily cuts. Using Magic Shave instead of a razor helps avoid the razor bumps that come from shaving black hair. (It’s how I still have a smooth babyish face after all these years. 😉) Seeing it on screen immediately reminded me of when I was young and my father, a former marine, did something similar. He, too, handed me Magic Shave and showed me how to use it, telling me never to put a razor on my face because it would ruin my skin.

Though the show is set in the 1990s, I was struck by how relevant the scene is now. In an age when Defense Secretary Pete Hegseth is demanding clean-shaven soldiers (a policy that will disproportionately harm Black servicemen), that tiny gesture said more about power and belonging than any speech could.

Messaging on the Ballot and the Screen

I keep thinking about that scene in the context of this election week, as we’re all trying to make sense of where we are. Because what that scene shows, and what our politics so often fails to, is the power of communication that actually sees people.

That’s the through line for me: from government to Hollywood, from the White House to Boots. Representation isn’t just visibility; it’s communication. It’s about whether people see themselves reflected in the institutions that shape their lives.

And there’s a difference between representation and understanding. It’s one thing for Boots to feature Black actors. It’s another thing to know that they have black folks making decisions. That small act on screen, of a Black man passing down what he knows about something as simple as shaving, told me they did.

That scene worked because it told the truth without explanation. It didn’t flatten experience into a slogan or an ad. It trusted that some people would know…and that knowing would matter. Whether on screen, at the White House, or at City Hall, the same test applies: are we communicating as if it matters? Are we using every available channel to affirm, to tell the truth, to govern smartly?

Don’t get me wrong - Boots certainly isn’t perfect. Most content, even the most thoughtful, has holes and blindspots. (That goes for candidates, too.) But that a single silent gesture between two Black men conveyed more truth about power and care than entire institutions often do. In a way, it said a lot about the true work of politics. This is a major part of the responsibility — to turn that private wisdom into public intelligence and make that kind of recognition systemic.

We can win if we leverage all of the channels at our disposal, whether it’s the infrastructure that controls our screens or our public offices, corporate board rooms or university campuses. We must fight for those channels, and when we have them, we must use them well. Mamdani has the chance to do just that.

A New Chapter: Freedom Table with NewsOne

One last thing: here’s my latest article with NewsOne, a legendary Black-owned platform, rooted in telling our stories and engaging the culture. I’ll be publishing pieces there, too, in addition to the newsletter. I’ll also be the host of a new monthly conversation called Freedom Table, where I’ll bring on guests, including organizers, journalists, business leaders, strategists, and culture-makers. The first conversation is coming up, and I’ll be sure to tell you more.

How We Win

Every few weeks, I’ll share my thoughts on movement strategy, politics, and the fight ahead.