Since I teach philosophy, I am sometimes asked about how to win an argument. Being a philosopher, I always engage in a philosophical discussion rather than providing tips on how to destroy with “facts” and “logic.”
In philosophy, an argument is a set of claims. There are two types of claims in an argument: one conclusion and one or more premises. The conclusion is the claim that is supposed to be supported by the premises. A premise is a claim given as evidence or a reason for accepting the conclusion. As such, to make an argument requires making a point (conclusion) and backing it up with evidence or reasons (premises).
When assessing an argument there are two main factors to consider: the quality of the premises and the quality of the reasoning. When assessing the quality of reasoning, the question is: Do the premises logically support the conclusion? If the premises do not logically support the conclusion, then the argument is flawed, and the conclusion should not be accepted based on the premises provided. The conclusion may be true, but a flawed argument gives you no logical reason to believe the conclusion because of that argument. If the premises do logically support the conclusion, then you would have a good reason to accept the conclusion, on the assumption that the premises are true or at least plausible.
When assessing the quality of the premises, the question to ask is: are the premises true (or at least plausible)? While the testing of premises can be a rather extensive matter, it is reasonable to accept a premise as plausible if it meets three conditions. First, the premise is consistent with your own observations. Second, the premise is consistent with your background beliefs and experience. Third, the premise is consistent with credible sources, such as experts, standard references, and textbooks.
In terms of winning, the constructing of a philosophical argument in isolation is like playing solitaire—winning is not beating someone else. A solitaire win would be constructing a good argument with plausible premises. But this is certainly not the sort of winning that people are interested in—what they want is the victory conditions for an argument against another person or persons.
In the case of arguing philosophically, the contest would be settled in favor of the best argument(s). As such, winning is a matter of having better logic and more plausible premises than the opposition. In the ideal, the result would be to find something (likely to be) true. Such contests must also be conducted in good faith and in accord with the philosophical principle of charity. This does not mean that the two sides cannot be engaged in an intense dispute in which claims and logic are called into question. To use an analogy, competing in such an argument is analogous to competing in good faith in a fair athletic event: one abides by the agreed upon rules and does not cheat. And of course, victory goes to the one who earns it by making the better arguments. Obviously enough, this is not the sort of winning that people tend to have in mind when they think of winning an argument. What people tend to think of is something Ben Shapiro is YouTube (in)famous for: his guide to winning arguments against leftists. The underlying view of winning is not unique to Ben Shapiro and one can easily trace this notion back to the Sophists of ancient Greece—and no doubt even further into the shadows of time.
In this context you win if the audience believes you and rejects your opponent—whether what you are claiming is true or not. While philosophical arguments can be used to persuade people, they tend (as Aristotle noted) to be the weakest means of persuasion. As such, if you want to win an argument, then good logic is probably your worst choice of tools. Fallacies (errors in reasoning) are far more effective than good arguments as tools of persuasion. Rhetorical devices, which rely on emotive force, are also effective at persuading people and thus are better weapons of victory than good arguments. While a fallacy can have a true conclusion and rhetoric can be used to dress up the truth, these tools do not reliably lead to the truth. Used well, however, they can reliably persuade.
Philosophers are often critical of this concept of winning for reasons like why honest athletes are critical of cheating. To use an analogy, consider winning a marathon. One way to win the marathon is to train hard, complete the competition fairly, and earn the first-place finish. But there are other ways to win the first-place prize. One option is to compete unfairly by using pharmaceuticals or blood doping. Another option is to secretly cut the course. One could even bribe officials. There are many ways to “win” and get the prize without competing in good faith. An argument can be “won” using fallacies, rhetoric and lies—that is, one can be crowned the winner in the same way as the marathon cheat gets their laurels.
It could be countered that in argumentation what really matters is winning. So if a politician or YouTuber can expand their base and profit by persuading people to accept their views through fallacies, rhetoric and lies then they have beaten their opponents—even (or especially) if their opponents are making true claims. The obvious counter is to draw the analogy to sports: winning matters but winning must be earned through an honest path to victory. Otherwise one is stealing the laurels. Having the trophy does not make one the best. “Winning” does not make one right.