In April 2011, President Barack Obama delivered a biting roast of Donald Trump at the White House Correspondents’ Dinner, an event that would later be seen as a pivotal moment in their political rivalry. At the time, Trump, a reality TV star, had been a vocal proponent of the ‘birther’ conspiracy theory, falsely claiming that Obama was not born in the United States and thus ineligible for the presidency. Obama’s decision to release his long-form birth certificate just days before the dinner set the stage for his humorous yet pointed remarks. During his speech, Obama joked about Trump’s presidential ambitions, suggesting that a Trump presidency would bring unconventional changes to the White House, including turning it into a hotel, casino, or golf course. The President even displayed a satirical image of a remodeled White House adorned with Trump’s name. While the audience laughed, Trump sat stone-faced, visibly humiliated. Many political observers, including Trump’s former adviser Roger Stone, believe that this public shaming motivated Trump to run for president in 2016. Fast forward to Trump’s presidency, and Obama’s jest about White House renovations took on a surreal twist. The Trump administration razed the East Wing to build a lavish, gold-encrusted ballroom, a project that mirrors the ostentatious style of Trump’s private properties. Although Trump denied plans to name the ballroom after himself, senior officials reportedly referred to it as ‘The President Donald J. Trump Ballroom.’ This episode underscores the enduring impact of political humor and the complex dynamics between Obama and Trump, whose rivalry reshaped American politics.