All help is appreciated.

Ask him why he's a Republican, and why he supports McCain.

If he's an ideological conservative, then you can argue how radical and corrupt the Bush Administrative has been.  There's a fine line between shrinking government/deregulation (conservative principles) and the sort of wholesale transfer of wealth to cronies who play ball that this administration has indulged in.

If he supports McCain because of his service and heroism, point out that that very heroism has left McCain with a blind spot about the military and foreign policy.  McCain suffered for his country for years in a black box: he never had his faith in the military and its ability to provide solutions shaken.  He emerged from Hanoi with his belief in the military strengthened.  Now, that's generally a good thing--but it doesn't give him a lot of perspective on questions such as, like, was the Iraq policy foolhardy and has it failed.  Ask him if he thinks that having a relic of the Vietnam generation who never learned its lessons at the helm during our generation's foreign misadventure is a good idea.

Ask him about the Court.  It's the last barrier to an imperial presidency, which any true conservative should be skeptical of.  The Bush people's radicalism is most shocking in their attempts to redefine the balance of powers between the branches.  Is he willing to trade an untrammelled executive for no same-sex marriage?

Finally, ask him if he reads James McWhorter or if he's heard of Black Republicans for Obama.  I'm not too familiar but I imagine they have a website with good arguments.  I'd also recommend Andrew Sullivan as a (white) Reagan conservative who greatly admires Obama.  Pointing out voices that will appeal to his conservatism while showing Obama's strengths will be helpful.

Unfortunately, if your friend thinks Savage is a reasonable voice, you're going to have a long slog.  

I hope he responds reasonably.

to just give him the facts, talk sanely and don't expect him to change his mind or his ways right away.

Facts are a curious thing. If you let them seep in, then you can't ignore them.

seeing that the young man is from Haiti, I wouldn't be quite as surprised at his politics. In my experience, Non-American black men fall in all shades of the political spectrum, unlike we Americans, who do tend to be strongly Dem.

One of the most conservative people I ever met was the daughter of a high-ranking African official.

I have found that when talking to a republican or conservative about health care the best argument is one from a business aspect. The most anti-competitive thing American business has to deal with is employer sponsored health care managed by the insurance industry.

I lived in Michigan most of my life. I worked in the auto industry, as so many Michigan residents do (did), and am very familiar with the troubles of American corporations. More than once over the last couple of decades, a new auto plant has ended up being built right next door in Ontario instead of being built in Michigan. There are disadvantages to building in Canada, mainly higher taxes. It isn't because of unionization, the Canadian unions are as strong or stronger than the ones in the US. It isn't because of a trained labor force, both areas are equal in that regard. It isn't because of more favorable business regulation, if anything the Canadian regulations are more strict. It certainly isn't because of taxes. Canadian taxes are  higher. There's only one clear advantage to building in Canada - they have government sponsored health insurance. This removes a huge burden from the employer.

All over the world, the countries we compete with have this one huge advantage. Every developed country that we compete with has universal health care of one sort or another. Even China has this advantage. Employer sponsored health care acts as a huge tariff on American corporations. Remove this tariff and they instantly become more competitive. This would change the playing field immensely. I have found this argument to be far more effective than talking about 'fairness' or 'preventing people from falling through the cracks'.

This isn't the only argument to be made for UHC from a fiscal viewpoint. There is also the extra burden put upon our hospitals to treat the uninsured. Move people from emergency rooms to doctors' offices and you have another large savings. Put all people under a single plan and you have negotiating power with suppliers, like the drug companies. That's an advantage the govt foolishly gave away with the medicare drug plan. That's what happens when you favor corporate interests over those of the citizenry.

Once you show that UHC isn't simply some giant entitlement giveaway, you can get a person to reconsider some of the other policy initiatives promoted by Democrats.

I know that African Americans have traditionally sided with the Democrats by huge margins but I can't help but believe that a good chunk of them are conservative Republicans at heart (and may vote that way in the secrecy of the booth)

It just stands to reason that people choose their political orientation based on more than skin color.  If whites are split between the two major parties, what should keep blacks from being split?

I think that an Obama presidency will actually result in a large portion of African Americans peeling away from the Democrats and declaring their political freedom.

Once that barrier has been broken, they will lose that sense of obligation to the Democratic party.

How often have we all heard blacks complain that Democrats just take them for granted?  I'm certain the feeling is deeper than we acknowledge.

In 2000 I was working with an African American friend on a project in Los Angeles and just before the election we were talking.  He told me, "Do not assume that every black person you meet is a Democrat".

And, while so many of us believed that Gore couldn't lose, he also told me, "Anything can happen... Antything".

He was right, that's for sure.

Of course I do not want to lose Democratic party identification with any constituent group but don't be surprised of we discover more Black Republicans after Obama becomes president.

It just stands to reason that people choose their political orientation based on more than skin color.  If whites are split between the two major parties, what should keep blacks from being split?

In my opinion it's not skin color - although it looks that way.

If you look at how the AA population is distributed, by and large we tend to be concentrated in certain areas. In these areas, economic conditions tend not to vary widely (no million dollar mansions in Bronx), and education tends to be similarly narrowly focused. Once a black man gets a good education and a six-figure job, he's probably (like definitely) going to move.

If you have a group with similar background, demographics, location, education and finances - why would you expect that group to embrace wildly diverse politics?