First rule of holes
When you're in one, stop digging.
This is precisely the thing his most ardent critics have feared. He thinks there's a number after which you should not be allowed to keep your money. Oh, he hedged with his statement immediately prior. He said no one begrudges money that is "fairly earned". See, there's that famous liberal weasel word, "Fair". The problem is that "fair" is never defined. Let's assume for argument's sake that number is $5,000,000. I'd bet that if most Americans had that much in the bank they'd never work again and be happy about it. IIRC, Obama made about that much last year. Am I to believe he thinks he has "enough money"? If so, will he now donate 100% of his earnings to charity, or in keeping with his politics, the Treasury? If not, why not? This is a fundamental difference between Obama and the rest of America. Your average American wants to be a zillionaire. They believe it is their God given right to earn whatever they can, legally. They do not believe there is some magical number that is "enough". Sure some people who make tons of cash end up giving a lot of it away. That's the difference. They get to decide where that "extra" money goes. Not the government, not the President. Not anyone else. You're a Scientologist? You can give it to them. Or to a homeless shelter or PETA or Jerry frickin' Fallwell if you see fit. We do not want to live in a nation that stops your from earning as much as you legally can.
Obama would never draw that line in the sand. Even if he weren't included. Why not? Hollywood would turn their backs on him in a New York minute. Imagine if you told your movie stars, "Sorry, you will be taxed 100% for every dollar you earn over five million." They'd go completely insane. Rather, he'll demonize "Big Business", "Big Oil", "Greedy Bankers", and "Speculators". No mention of Big Hollywood, Big Labor or Big Lobbyists.
I'm not calling the man a Socialist or even small s socialist. I don't think it matters. I think what is important is that he does not believe there is any end to the power of government. He talked about "flaws" in the Constitution that hinder him from making broad sweeping changes unchecked. He doesn't think that there is, or should be, any limit to the amount of the US economy controlled by the Federal government. He wants to constrain people from making "too much". Socialist or not, doesn't matter. What does matter is that he's an authoritarian. That's the problem. Transparency? Gone. Gays in the military? Not gonna happen. Closing Guantanamo (remember that "fierce moral urgency"?)? Nope. And on and on and on.