Anyone ever heard of the guy? The guy is educated and informed, but he makes some mistakes in his arguments. He actually makes quite a lot of logical flaws, but very few people actually catch it (at least, the people on Youtube don't catch him). He is usually debating against people with little debate skills, so he often comes out on top. But, beating up on scrubs don't make you a good baller. The people he often debates against are trying to appeal to emotions, but the best way to "beat" him is to catch him in a logical flaw because many of his arguments are based completely that the logic is sound. Thus, any crack in his logic, then his entire argument falls apart. That's easier said than done (especially if you are on the spot), but it's very possible given his video clips.
Personally, I don't agree with him on all issues. He makes some good arguments, and he is entitled to his viewpoints. But, simply having a good argument doesn't mean that your viewpoint is correct. Other viewpoints may also have good arguments as well, and he often dismisses them. He probably does that on purpose though. Having a civil debate/discussion doesn't make good entertainment.
With all of that being said, let's break down some of his arguments (he made lots, so this might take a while). I should note that I only watch him on Youtube, and Youtube only shows mostly clips. Maybe he goes into more detail in the unedited video, but oh well. It is what it is at this point.
1. Shapiro believes in the 2nd Amendment because the people have the right to fight against government tyranny if needed. He also believes it is within 50 years (or so, the number changes). The problem with this argument is that he is actually arguing a different argument. Sure, some people from the left are arguing against the removal of all guns, but many others simply want modified gun laws. He might have an argument with the first group, but not the second group. The biggest problem with his argument is his time frame for such an event. It is based on nothing more than conjecture. Normally, that would not be a killing blow to an argument because that is simply how he feels. However, he bashes the opposition so hard because they base their arguments on conjecture, emotion, etc. If you point out that he is doing the same thing (basing an argument without evidence), then you got him. He loses....or at least he looks bad.
That was a lot. More as I feel like writing more....