Honestly, I actually took the time to try and see if Destiny has ever taken part in a serious debate with someone who is actually knowledgeable and educated in their field. I've seen several of his videos before and wasn't impressed, but I figured I'd do a deep dive. For the most part, he seems to focus on easy targets, like Dick Masterson, Jaden Paladin, No Bullshit, Sargon of Akad, Jon Tron, Laura Southern... essentially youtube bloggers, some of whom don't even cover politics. These people are not intellectual heavyweights, so I'm not sure why destiny deserves credit for picking easy targets who don't do research.
He did do a video with a professor named Gordon Menzies. From my research, he doesn't seem particularly well known, but he seemed pretty knowledgeable. I'll give the video credit for that. However, it wasn't a debate. Simply a discussion with a click bait title, which is par for the course for destiny. He loves click bait.
Looking up a list of his best debates on his reddit, I was temporarily surprised, and excited, to see Richard Wolff mentioned. Wolff was educated at Yale, Stanford, and Harvard, and has published several books. He is also a college professor. Sadly, while Mr. Wolff has offered to debate Destiny, it appears that Destiny has refused his offer repeatedly, realizing that debating an educated individual would, perhaps, be above his skill level. The reason Destiny implicated was that Wolff supported violence. I haven't seen this claim substantiated yet, and Destiny sadly forgot to provide evidence of this. However, even if true, it doesn't quite make sense, as Destiny has already debated extremist alt right figures in the past, and has even implied that political violence can potentially be justified under the right circumstances. The truth is that he's afraid to debate anyone who potentially knows what they are talking about.
It's easy to argue with a handful of people from /pol/ and look like you know what you're talking about. It's much, much harder to debate a tenured professor who is a renowned expert in their field, and have your core beliefs shaken. Especially when a loss can open you up for criticism from your own fan base, and hurt your financial bottom line.