Destiny's MO is a type of Socratic Method where he looks for the weak point in a worldview, then metaphorically struts around when he finds it as a huge "win." Even if that worldview still has much better explanatory power than his own.
His method doesn't work well against people with an encyclopedic knowledge of the subject, like Ryan Dawson. It also fails against people who are naturally gifted at speaking and rhetoric, like Nick Fuentes, or with a deeper understanding of philosophy, like Trent Horn.