Skip to main content

Success Quote by Donald Trump

"It's always good to be underestimated"

About this Quote

Underestimation is one of Trump’s favorite forms of fuel because it lets him cast every win as a shock and every loss as proof the system was rigged against him. On its face, the line reads like a standard business maxim: keep expectations low, then outperform them. In Trump’s mouth, it doubles as branding. He’s not just competing; he’s setting up a narrative trap where critics become the complacent villains and he becomes the insurgent who “nobody saw coming.”

The subtext is combative and theatrical. “Underestimated” implies an audience of elites, experts, and gatekeepers who think they know better. That’s an essential ingredient in Trump’s public persona: the wealthy outsider, the reality-TV brawler in a suit, the guy who claims he doesn’t need approval yet lives off the pleasure of proving people wrong. The phrase compresses grievance and confidence into a single, portable slogan.

Context matters because Trump has repeatedly used perceived disrespect as a political and commercial accelerant. From real estate dealmaking to campaign rallies, he thrives on the dynamic where the press, opponents, or institutions are framed as sneering and overconfident. If he wins, he’s the underestimated disruptor. If he loses, the underestimation becomes retroactive justification: they never gave him a fair shot.

Why it works is its emotional efficiency. It invites supporters to share in the comeback fantasy and pre-loads a reason to distrust negative forecasts. It’s less advice than a posture: turn skepticism into momentum, and treat doubt as proof you’re dangerous.

Quote Details

TopicMotivational
More Quotes by Donald Add to List
Its always good to be underestimated
Click to enlarge Portrait | Landscape

About the Author

Donald Trump

Donald Trump (born June 14, 1946) is a Businessman from USA.

74 more quotes available

View Profile

Similar Quotes

Harry S. Truman, President
Small: Harry S. Truman