It’s hardly surprising that Donald Trump tends to see the world as winners versus losers, but Trump’s definitions of winners and losers are unique, and don’t match how much others define them.
A winner is not necessarily the most honest, the most capable, or the most deserving individual, or even a respectable person who you’d want to associate with. It’s nothing about the person themselves—it’s all about how the world sees that person and their standing. A winner is someone who projects success, glamour, toughness, and, above all, relevance. A winner has a constituency, a following, an audience, a crowd that affirms their status—even more simply put, as Trump is prone to saying, “a star.”
Conversely, a loser is not defined by crime, immorality, or even failure in the traditional sense. Being a loser has more to do with status than any innate reflection of self-worth—someone who has lost their constituency, someone without glamour, someone who threatens to taint and tarnish Trump’s brand with their own failure.
Yet, paradoxically, the more interesting nuance that few appreciate is that Trump doesn’t always fully abandon losers, contrary to public perception, even in cases where most would be running for cover. If they retain a constituency, if they remain sympathetic victims in the eyes of certain groups, or if their plight can be repackaged as proof of Trump’s own persecution, these losers become useful to him.
Similarly, many have been surprised by Trump’s magnanimous treatment of former critics who retained independent stature, but they should not have been surprised. Figures like JD Vance and Marco Rubio, who had previously attacked Trump in deeply personal terms, were ultimately welcomed into his inner circle. Their prior opposition was not disqualifying; if anything, it enhanced their value. The conversion of a high-profile critic into a loyal ally serves as a powerful demonstration of dominance.
These examples reveal a key principle: Trump treats those with independent constituencies differently from those without them. Individuals whose influence derives solely from proximity to Trump are inherently disposable. Those who bring their own audience, reputation, or power base are handled more carefully—and often given greater latitude.
The essential truth underlying all this, is that Trump’s relationships with others are governed by power. An astute student of power, Trump is more likely to discard those he believes he “created,” or who are solely dependent upon him, while accommodating those whose influence exists independently and whose followers represent an important new potential constituency to woo.
Trump’s calculated approach to retribution follows a similarly calculated logic. Contrary to the image of indiscriminate vindictiveness, he tends to target individuals he perceives as vulnerable—those lacking strong constituencies or cross-sector institutional support. He tends to avoid conflicts he cannot win and often prefers to drown the squeaky wheel in oil, so to speak, by pacifying opponents by bringing them into the tent rather than confronting them directly.
This little-understood selectivity reflects a broader strategic instinct. Trump does not pursue revenge simply for its own sake; he uses it as a tool—to deter rivals, eliminate threats, and reinforce his authority. His targets are chosen not randomly but based on perceived weakness and limited capacity for retaliation.
Critics argue that ultimately, this worldview reduces human relationships to transactions. Everything is transactional. Friendship, loyalty, and even animosity are fluid categories, constantly shifting based on utility and advantage. Individuals move seamlessly between being allies, adversaries, instruments, foils, and cronies.
In this framework, there are no permanent friends—only temporary alignments of mutual interest. Even inner circle advisors are not so much genuine confidants as much as they are followers whose status derives from proximity to the center. Even these relationships are unstable, requiring continual usefulness to endure.
In the end, Trump’s world of winners and losers may not fit most conventional definitions of winners and losers—but it fits a calculated logic all of its own nonetheless, one which prioritizes power above all else.
Pre-order the Book Today
Trump’s Ten Commandments: Strategic Lessons from the Trump Leadership Toolbox reveals the calculated strategies behind the daily headlines. Beyond the “Wall of Sound” media dominance explored above, Sonnenfeld unpacks nine other distinct commandments—from his “Divide and Conquer” tactics to his “Hub-and-Spokes” management style.
Pre-order here: https://worth.com/trumps-ten-commandments/
