How Far Jokes Can Get You in Politics

Trump leaned into comedy to engage his audience, with many of his rallies resembling a stand-up routine filled with humor that resonates with supporters and shocks adversaries.

Both times running for president, Trump's tactics have divided the nation, with comments that assist in alienating (some) minority voters. Photo by Tabitha Kaylee Hawk on Flickr

I don’t know if you all know this, but there’s literally a floating island of garbage in the middle of the ocean. I think it’s called the United States of America.

*Cue the laughter* Oh wait? Is that offensive? How could I call this country an “island of garbage”? Well, if it can be said about Puerto Rico, then the same must be true about the U.S. Or so goes the assumption originated by Tony Hinchcliffe.

Los Angeles-based comedian Hinchcliffe was one of the scheduled speakers at Donald Trump’s presidential gala at Madison Square Garden on Oct. 27. Between the typical stand-up shtick and his endorsement of the former president — now president-elect — Hinchcliffe proceeded to make insensitive and inappropriate comments for some laughs. 

Within minutes, his “comedy” took to the headlines, most often referring to his comment about Puerto Rico being an “island of garbage.”

In a time where entertainment and politics are increasingly intertwined, Trump’s choice of a comedian like Hinchcliffe signals a distinct shift in his campaign strategy, especially in the final days before he was elected. Intending to appeal to voters who tend to favor raw, unfiltered speech, I have to admit that Trump made a good choice of speaker. He’s leaned on comedy to engage his audience; many of his rallies have resembled a stand-up routine, with humor that resonates with supporters and shocks adversaries.

However, having a professional comedian deliver a series of edgy and potentially offensive jokes — especially aimed at Latino and Puerto Rican populations — risks overshadowing Trump’s political agenda itself. Instead, what could have been intended as satirical critiques alienated some undecided voters. 

Comedians have long played a role in political discourse, but the stakes seem different when a performer like Hinchcliffe walks on stage at a formal campaign event. Hinchcliffe’s punchlines blur the line between humor and endorsement, potentially muddying Trump’s platform with controversy-laden jokes. 

While some may view his presence as a refreshing injection of humor over such serious topics in a political speech, others see this as a serious misstep, raising questions about the role comedians should or should not play in political spaces.

But Trump’s “tell it how it is” persona captures the audience like none other, especially when his comments are directed at Vice President Kamala Harris. Among other things, he got the crowd roaring by saying she would be “like a play toy” for world leaders. 

Trump’s rally was, in many ways, a spectacle of political performance. This kind of rhetoric isn’t new for president-elect Trump, but it is worth asking: what does it achieve? 

Can you imagine speeches for an 8th-grade class president election that include yelling “world-class liar” or “pathetic”? Probably not. But this is the example we’ve been shown with every presidential election that includes Trump.

On the one hand, Trump’s supporters see these comments and jokes as a man who’s charismatic and unafraid to tell jokes and throw punches. The laughter filling the stadium at Madison Square Garden was a testament to how deeply his rhetoric resonates with his base.

On the other hand, critics see these rallies as emblematic of the deeply troubling trends in politics today. What once was considered inappropriate and childish behavior from world leaders is now being celebrated. They see this rally, and others similar to it, as a political event and a reflection of the nation that keeps lowering the bar. 

Yet, from a purely strategic standpoint, it worked… somehow. Trump’s blend of humor and populism has let him dominate headlines and energize his base. He swiftly taps into his supporters' fears and frustrations, keeping him at the center of the political conversation.

This is a sobering moment for America as a nation. The fact that a former president of such a powerful country can get by making ignorant and inappropriate remarks says more about the country than it does about him.