Ha, if that ever happened, he could just dodge it by talking about how he was helping out a family member who needed his help. It's hard to attack a man who's helping out his half-brother who lives in a shack, especially if he is sending his own money to do it. An attack could backfire pretty heavily on Republicans if Obama played his cards right.
If Obamacare isn't enough, how about him telling Joe the Plumber "I think it's good for everyone when you spread the wealth around".
http://www.youtube.com/watch?v=OoqI5PSRcXMSeems like that's a pretty big statement in favor of wealth redistribution.
And GB, you say you support free markets, yet support government money being handed out to people?

No offense, but those two are pretty incompatible. Spreading the wealth around is a disincentive to wealth creation. Why start a small business if the government is just going to take your wealth and spread it around, especially if you are already receiving some of the wealth that is being spread around by the government?
And before you mention that this stuff already happens on a regular basis, let me just mention that I am opposed to all forms of subsidies and government handing out money.
Americans are more than capable of freely spreading their wealth around, and private charity has a much larger beneficial effect than government handouts, probably because private charities usually require some form of commitment by the beneficiary.