How to Misunderstand the American Dream Like Donald Trump

The Political Pivot: Early Losses as Fuel for 2016

Trump's journey in politics is itself a tale of "failing up." After making early flirtations with politics in the 1980s, 1990s, and early 2000s, he made an unsuccessful attempt to run for the presidency in 2000 under the Reform Party. He pulled out of the race, stating that the party was "self-destructing," which allowed him to reframe his exit as a strategic decision rather than a political loss. His early political ventures might have been forgettable for most candidates, but Trump repeatedly referred back to them as early signs of his political ambition.

When he announced his candidacy in 2015, he painted himself as a political outsider, claiming that he alone could shake up the system. Rather than letting his earlier foray into politics remain as a memory of "almost" running, he used it as a launching pad for his rhetoric about disrupting the political establishment. The perceived failure of those early bids became a narrative asset, reinforcing his outsider status and portraying him as a unique figure willing to disrupt politics as usual.