The Donkey Boys

Remember Pleasure Island from Pinocchio? It was a place where boys could indulge every whim and whimsy, freed from the world’s expectations and rules. It was a land of wild freedom and reckless abandon, where laughter echoed off carnival rides and mischief was the only currency. But beneath the joyful clamor, something darker brewed. Those who stayed too long, who reveled in their rebellion without a thought to tomorrow, began to change. Their laughter grew hoarse, their features twisted, and one by one, they transformed—no longer boys, but braying donkeys, burdened and led away, forever trapped by the very freedom they had sought.

Today, a new breed has emerged from the edges of society—men who seem like those lost boys resurrected. I call them the “Donkey Boys.” These men, hardened by defiance, cling to a rugged vision of “real America” like a fading flag, rallying around a version of hyper-masculinity that scorns modern complexities and celebrates raw power. Like those boys on Pleasure Island, they bray loudly, wearing their anger as armor and their aggression as identity. While the world around them grows and changes, the Donkey Boys hold fast to a dream of yesteryear, casting themselves as warriors against a tide they refuse to understand.

Now, these Donkey Boys (also referred to as DBs) have found their way into the morass of American politics as an emerging voting bloc. Led not by traditional figures but by voices from behind microphones and screens, their influencers are podcasters with counter-culture opinions, Twitch streamers who thrive on spectacle, and tatted up and yoked professional athletes. They gather followers in virtual coliseums, where debates are battles, and loyalty is forged through shared defiance. These leaders rally the Donkey Boys with a call to action that resists nuance and rejects compromise, a force intent on shaping the country with a stubborn nostalgia for a world they imagine as “real America.” As elections approach, their presence looms larger; they’re large draw gaining even the attention of presidential candidates.

Donkey Boys Defined

The Donkey Boys aren’t just unhinged tough guys—they’re the product of an ideological echo chamber. To them, “freedom” isn’t about collaboration but a gritty, hostile autonomy, where “rights” mean acting without regard for consequences. Vulnerability? To DBs, it means you’re a beta. They cast themselves as defenders of “authentic” masculinity, the self-appointed gatekeepers of what it means to be a “real man.” They’re fiercely combative, responding to any challenge with a bulldog mentality, even if it tramples the nuances of complex social dynamics. Although frequently claiming to be critical thinkers, they’re world is very binary. You are either strong or weak, Alpha or simp, man or woman, etc. 

Politically, DBs posture as anti-establishment heroes while supporting figures who tell them what they want to hear. Their online playgrounds amplify their voices, letting them operate as champions of an unsentimental, “take-no-prisoners” culture. Rather than engage thoughtfully, they rally around clichés—especially those that pit them against any who would suggest that empathy or vulnerability is a strength.

The Roots of the Donkey Boy Movement

The DB mindset isn’t unique but finds fertile ground in the existential disillusionment of Gen X and Millennials who feel robbed by society’s promises and terrified of shifting gender roles and fluid sexual identities. Raised in an era of economic disruption, social shifts, and growing distrust, these men are grasping at a myth of rugged individualism that paints cooperation as cowardice. They’re angry, alienated, and gravitate toward figures who romanticized a harder, "no-nonsense" masculinity. And now, these ideas are bleeding into Gen Z, where DB culture grows more visible each day.

The DBs draw on a tapestry of disillusionment stitched together by broken institutions, from the fallout of 9/11 to the betrayals of the 2008 financial crisis. These moments have left scars. Facing a world that promotes “softness” and inclusivity, DBs dig in their heels, clinging harder to old-school masculinity. Voices from Joe Rogan to the ghost of Ayn Rand fuel this resurgence, branding it as a return to realness —a defense against the creeping infection of political correctness and sensitivity.

Why DBs Are Pro-Trump and a Key Voting Bloc

Donald Trump is a natural fit for the DB ethos. He’s unapologetic, brash, and seemingly unfiltered. He offers the sort of validation they crave, reinforcing their sense of grievance and belonging. Trump’s anti-woke rants, his demonization of the elites (although he is one), and his claims of persecution resonate with DBs because he mirrors their own story. For them, he’s more than a candidate—he’s a beacon of masculine power in a world increasingly hostile to their values.

This group isn’t some fringe; it’s a rapidly consolidating voting bloc. DBs fall into a demographic of men aged 18-45, largely without college degrees, whose lives don’t often align with mainstream narratives. In swing states, DB turnout has the power to shape elections. The polls reflect their loyalty: Trump’s favorability among these men remains disproportionately high, and they rally behind him with fervor.

The Surprising Ethnic Diversity of the Donkey Boys

Contrary to the stereotypical image, DBs aren’t just angry white men. The Donkey Boy identity appeals across racial lines, tapping into cultural values of resilience, independence, and distrust of the mainstream. Many Latino and Black men, who feel equally marginalized or ignored, find resonance in DB ideals. Influencers in various communities spread a similar message of "self-reliance,” turning Donkey Boy culture into a melting pot of dissatisfaction and resistance. Examples: former Proud Boy leader (and now federal inmate), Enrique Tarrio and Kanye West.

For these men, embracing the DB mentality is less about identity politics and more about claiming a sense of control in a world that feels otherwise indifferent. They share a disdain for “softness,” seeing in this ethos a pathway to reclaim agency. For some, it’s a reaction to society’s attempt to paint over their experiences with slogans of inclusivity that feel as hollow as the institutions pushing them.

How to Spot a Donkey Boy

Hyper-Masculine Posturing: DBs crave a self-image of the “real man”—dominant, unapologetic, invulnerable. Social media is their arena, plastered with flexing gym selfies and “alpha” quotes to display a life of gritty resolve. Examples: Logan Paul, Nick Bosa

Misinformation Evangelism: DBs view mainstream media as the enemy, instead turning to a network of conspiracy theories that reassure them they’re onto “the truth.” Figures like Russell Brand, Alex Jones, and fringe YouTubers validate their worldview with a blend of pseudoscience and sensationalism.

Selective Patriotism: Patriotism, for DBs, means loving America only on their terms. They defend the “true” values of the country, where freedom means the right to impose their views without pushback. Figures like UFC’s Colby Covington espouse this selective patriotism, exemplifying the contradiction of loving “freedom” while seeking to silence dissent.

Misogyny Disguised as ‘Traditional Values’: At the heart of DB culture is a hostility toward women’s worth and independence. Influencers who talk about “returning to real masculinity” feed into the DB worldview that sees women as appendages to male power. Examples: Andrew Tate, Dan Bilzerian

Twisted Version of Critical Thinking: DBs fancy themselves as freethinkers but recycle simplistic talking points as if they were the words of the wise. They lean on rhetorically clever influencers, hoping to sound intellectually engaged without challenging their assumptions. Example: Charlie Kirk, Elon Musk

Hero Worship of Strongmen: DBs idolize those who shun societal “rules.” They see figures like Mike Tyson or RFK Jr. as icons who resist the status quo, validating DB disdain for compromise.

Anti-Establishment…With Conditions: DBs champion rebellion selectively, raging against “government overreach” unless it reinforces their agenda. Fueled by the likes of Tucker Carlson or Jordan Peterson, they don’t see the irony in this flexible anti-establishment stance; to them, rebellion is only problematic when it threatens their freedoms.

“The inner boy in a messed-up family may keep on being shamed, invaded, disappointed, and paralyzed for years and years. ‘I am a victim,’ he says, over and over; and he is. But that very identification with victimhood keeps the soul house open and available for still more invasions. Most American men today do not have enough awakened or living warriors inside to defend their soul houses. And most people, men or women, do not know what genuine outward or inward warriors would look like, or feel like.” - Robert Bly

How to Talk to a Donkey Boy

Talking to Donkey Boys is an exercise in patience and subtlety. Confrontation, especially when direct, rarely penetrates their defenses. Instead, an approach rooted in Critical Intelligence—a blend of self-awareness, intellectual rigor, and ethical insight—can create the space for reflection without triggering resistance. Rather than challenging their views head-on, the goal is to ask questions that bypass the armor and encourage a glimpse into the deeper layers of who they are. Here’s how, with some carefully crafted questions:

Who is someone you respect that has very different views than you?

This question encourages them to think beyond their echo chamber and acknowledge value in perspectives they might otherwise dismiss. It’s not about agreeing but finding a common ground of respect.

Who is someone you feel safe to be vulnerable with?

DBs often operate from a place of armor and defense, making vulnerability feel risky. By asking this, you invite them to consider moments where they felt safe enough to drop the mask, even briefly.

What is the legacy you want to leave?

Legacy taps into a sense of purpose and what they’d like to be remembered for. This question asks them to look beyond the immediate battles and think about the lasting impact they hope to create.

What fear are you most afraid to express?

Fear is often masked by aggression, bravado, or defiance. By inviting them to name this hidden aspect of themselves, you help them confront a truth they might not be willing to show on the surface.

Who would you lay down your life for?

This question dives straight into the heart. It asks them to confront what, or who, they value most deeply. It often reveals a sense of loyalty, love, or duty that may lie beneath the anger.

These questions are designed to transcend the ego and enter into the realm of authentic self-reflection. By inviting them to look beyond surface identities and into the core of their beliefs, fears, and values, you encourage a moment of introspection. And in my view, this is the only way to truly reach them. It’s not about proving a point but creating a bridge to something deeper—because real connection begins when the armor, even momentarily, comes off.

Closing Thoughts

The Donkey Boys represent something we should take seriously. They are, after all, a mirror of a society that’s left too many feeling irrelevant and angry. This isn’t just a passing phase; it’s a movement rooted in deep resentment, nostalgia, and the search for belonging in a world that’s moving away from rigid identity constructs. To ignore DBs would be foolish, but to confront them in traditional ways misses the point entirely. Understanding their perspective is essential if we are to defuse the ideological time bomb that’s ticking within this group. The question remains: can society evolve without leaving people so far behind they’d rather see it all burn than change?