You're misinterpreting, he isn't literally wishing that someone becomes broke. He's implying that "his" community is taking advantage of systems like welfare and exploiting them rather than using them in a way to create job opportunities for themselves. So, he's saying that he wishes that there was more risk in "becoming broke" rather than just knowing you can fall back and depend on government assistance.

Also, what's going on at the Trump rallies is just sad. Protesting is an exercise of the First Amendment, not an act that allows you to abuse someone else's First Amendment rights. How the hell is it American to prevent someone else from speaking to thousands of people who want to hear them?

When you see that a Trump rally has been interrupted and stopped on the news, you probably think, "Wow, what a bad guy, he must be doing really terrible things for people to do that!" when the reality is that this is the existence of the guy who rushed at Trump's stage: https://twitter.com/Younglionking7
He's literally a Tumblr-using, attention-whoring, Instagram-filtering, wannabe revolutionary who is doing absolutely everything in his power to get money, attention, interviews, etc. He's just a loser. He has no real message or cause.

NdGT said it pretty well in that tweet the other day: