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The Art of the Grift: How Trump’s Business Savvy Falls Short in Leadership

Trump’s time in office—and his legacy beyond—reveals a troubling gap between business swagger and genuine leadership.

Libby Winkler
4 min readDec 22, 2024
Photo by 은 하 on Unsplash

The Art of the Grift: How Trump’s Business Savvy Falls Short in Leadership

Donald Trump’s journey to the presidency was built on a larger-than-life persona: the self-made billionaire, master negotiator, and sharp-witted businessman who vowed to bring corporate efficiency to government. For many voters, this promise felt logical. Why wouldn’t a man with a track record of building an empire bring that same success to running the country?

Yet, Trump’s time in office—and his legacy beyond—reveals a troubling gap between business swagger and genuine leadership.

The Business Genius Myth

Before unpacking Trump’s leadership flaws, we must peel back the myth of his business brilliance. Far from being a symbol of entrepreneurial mastery, his empire has been marred by bankruptcies, legal battles, and dubious practices. Iconic landmarks like Trump Tower or the glitzy success of The Apprentice may have burnished his mogul credentials, but many of his ventures—from airlines…

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Libby Winkler
Libby Winkler

Written by Libby Winkler

Freelance writer who loves exploring the messiness of humanity, while poking around in nooks of life and shining light on all the things that make us complex..

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