At Donald J. Trump’s rally at Madison Square Garden, a diverse crowd of Make America Great Again (MAGA) supporters, patriots, and politically engaged constituents gathered with anticipation. However, the mood shifted when comedian Tony Hinchcliffe took the stage. It quickly became evident that many in the audience were unimpressed. In my view, the Trump campaign made a significant miscalculation by selecting Hinchcliffe as the opening act. Personally, I had never heard of him, and many of my friends and colleagues were equally unfamiliar. Frankly, I doubt we will hear much from him again in this political context.
Hinchcliffe’s dark roast style of comedy may work well in a traditional comedy setting, but it was entirely out of place at this rally. His performance, better suited for a roast, clashed with the tone and values expected at a political event of this scale. There is a time and place to push boundaries in comedy, but this was neither the right platform nor the right audience.
As a strong supporter of free speech and a fan of comedy, I want to be clear: Hinchcliffe has every right to perform his material. However, with freedom of expression comes responsibility, and this performance clearly missed the mark.
I suspect that a particular faction within the Trump campaign team was responsible for this decision, and I believe they will face consequences at the polls. This misstep is likely to cost Trump votes, especially in key communities where he is striving to build support.
I would like to address one specific part of Hinchcliffe’s set. Growing up in the Bronx with Puerto Rican friends and having recently visited Puerto Rico myself, I have come to deeply appreciate its culture, history, and people. While Hinchcliffe’s joke may have been intended as a political commentary, the delivery lacked context, substance, and sensitivity. The result was a joke that did more harm than good.
Puerto Rico, like any place, has its challenges, but its beauty and rich culture far outshine those issues. Today, while escorting voters to polling sites, I had several conversations, and the Trump rally—specifically Hinchcliffe’s set—was a major topic of discussion. The consensus was clear: people felt disappointed, and the campaign’s poor judgment did not go unnoticed.
Trump’s campaign has made several strategic errors that, if handled differently, could have fostered more unity. Instead, choices like this alienate the very communities he needs to win over. The candidates and communities that could strengthen his platform are now left questioning the direction of his campaign.
While I do not believe this particular mistake will cost Trump the presidency, it is certainly a blunder his campaign cannot afford to repeat. It is something I wish I had not seen or heard, and I know many others feel the same way. The Trump campaign must reflect on these errors if they truly hope to build the unity they seek.
