Why does Romney constantly remind everyone he's rich?

[Volrath50]

It seems every time Mitt Romney opens his mouth, he says something to remind everyone how fabulously, flaming wealthy he is. This has generally been to the detriment of his campaign.

Now there's nothing wrong with being wealthy, however, no one likes someone who constantly and endlessly reminds everyone just how much richer they are than them.

Romney's smart enough that he ought to know that this isn't helping him, and plenty of rich people can go more than a few hours without constantly telling the world just how extremely wealthy they are.

So the question is, why does Romney keep doing this, over and over and over? Is he insecure about something, so much so that he needs to keep reminding everyone that he could sleep on a mattress stuffed with $100 bills? Is his campaign not telling him that he comes across as a caricature? Does he think that voters like to constatly hear how many orders of magnitude wealthier he is than them?

This is really perplexing me.

[Volrath50]

I think it just depends how much it bothers you.

I'm 23 and working, but I only have a couple grand in the bank. My family was and always has been middle class. Nevertheless, I don't look down on the rich or the poor. People obsess with money far too much.

He's rich. I'm not. Who cares? Just because someone made money doesn't mean that they "owe" somebody else money just because the other person might not have made as much.

What I'm asking has nothing to do with the fact that he's rich, only the fact that he keeps pointing this out, repeatedly, in a way that hurts his campaign. Romney's an intelligent man (part of the reason he's rich), and ought to know that people prefer a candidate that's humble to one that seems to be unable to go a day without pointing out just how much richer he is than everyone else. People generally don't dislike people for being wealthy, but they do dislike them for repeatedly pointing this fact out.

There are other politicians in Romney's category of wealthyness, who have gone virtually their entire career without the sort of "Look at me, I'm super-duper rich" comments that Romney makes on a near daily basis.

[Volrath50]

How I look at it is that by mentioning his wealth, Romney reminds voters that he has had success in the private sector unlike Obama whose only success has been in government and liberal organizations. By bringing this up often, he makes Obama look like a candidate who is out of touch with what goes on beyond the Washington D.C. ivory tower and ruling class. I don't take it as elitist at all and think it's a great strategy to attract concerned voters who are struggling financially.  They can see Romney as an inspiration.

I'm now imagining an ad going something like this:

Success in life is measured by one's wealth. And I am extremely wealthy. I am richer than Obama, richer than you, and richer than all the other candidates combined. I will thus be the most successful president we have ever had. I will inspire our economy to flourish. All the folks out there struggling financially will see me as an inspiration, and our economy will grow as they try to be like me. I'm Mitt Romney, and I approve this message.

Think it could work?