It’s always good to be underestimated.

The remark frames being underestimated as a strategic advantage: low expectations reduce scrutiny and pressure while creating room to outperform and surprise rivals. In Trump’s public persona—built around competition, negotiation, and media spectacle—the idea also functions as a rhetorical posture: presenting oneself as dismissed by elites or opponents can energize supporters and set up a narrative of vindication if success follows. More broadly, the quote reflects a common competitive mindset in business and politics: perceived weakness can be leveraged to gain freedom of action, conceal intentions, and turn later achievements into a more dramatic proof of strength.