08/27/2012 04:09 pm ET Updated Oct 27, 2012

New Game: Sway the Swing Voter

I just don't understand swing voters. I simply do not get them.

The swing voter, that maddening, allegiance-changing species. A demographic so thin they are counted in the single percentage digits this year, but so utterly powerful that they will decide the election, just as they've decided every presidential election since anyone can remember. The media rush around looking to characterize them -- soccer moms! Blue-collar workers! Unemployed a cappella singers! -- but ultimately they can't, because the only category they fit is the one they created for themselves.

To become a member of this group, all you have to do is not know whether you're voting for Barack Obama or Mitt Romney.

But how is that possible? Romney has been running for president for more than a year (longer if you count his 2008 attempt), and Obama has held the actual office for almost four. Moreover, these candidates obviously embody two distinct points of view about how to govern the country. Yet a billion dollars may be spent by the time this is all over trying to reach this tiny, tiny group, to get them to make up their mind by election day.

We could be over and done with this by now if it weren't for these people.

I was shocked some years ago to learn that one of my own relatives is a swing voter. My brother-in-law, a recently retired Navy captain, changes allegiance to parties whenever the mood suits him. Dubya this year, Obama that. I spent an entire beachside family reunion in 2004 arguing with him -- well, drinking and arguing, and arguing respectfully, because if you take this stuff too seriously, especially when family is involved, you will go nuts -- but without any better understanding of how he makes his decisions. It's all gut check, if you ask me.

But what a gut check! My brother-in-law is a swing voter with a winning streak. He's voted for the winning president every four years since he started voting in 1984. That's seven out of seven! Here's a quick rundown of some of his votes, with his explanations attached:

1984: Ronald Reagan: "Reagan was going to kick the Russians right in the jimmies, so voting for him was a no-brainer."

1992 Bill Clinton: "Clinton is just a very charismatic person, and I thought he did well versus Bush 41 in the debates. I thought Clinton was younger, had more energy, and his ideas made sense."

2000 George W. Bush: "I think I just liked him more than Al Gore. Bush, even though he stumbled during interviews, seemed more down to earth and trustable. I think Cheney was a shrewd choice for VP, as well."

2004 Bush: "We were at war, and I felt that Bush/Cheney would do a better job than Kerry in carrying out the war. I know that many people don't agree with our decision to go to war. I do. We were attacked, and to do nothing would enable more attacks in the future."

Given his answers, and some other thoughts he's shared with me over the years, my brother-in-law is not guided by any real ideology as much as a belief in his own, Wisconsin-bred, center-right sensibility. The culture war doesn't register with him. Whole swaths of issues concerning race, class, and gender, at least as they relate to his political decisions, do not concern him. He clearly wants a strong military and a strong economy, but he isn't too concerned which political party assumes responsibility for those tasks.

Any focus group organizer would be daft to not make him a permanent attendee on any group requiring the participation of a "regular middle-aged white guy."

So it's another election year, and my brother-in-law is not quite sure for whom to vote. He's got an idea, but it's not set in stone yet. He wants to see the conventions. He wants to see the debates. A Wisconsin native, he likes Paul Ryan ("He has my values. He hunts, he fishes, and he probably loves the Green Bay Packers. He's handsome."), but he also likes Obama ("I like his sense of humor, timing and the fact that he is a sports fan. I like his wife and I think he has a nice family.").

I respect my brother-in-law. He's a voracious reader, and I'm sure he knows everything there is to know about Navy submarines. And he can beat me at the arcade version of Ms. Pac-Man every single time. But every four years he drives me nuts.

This is what I propose: You persuade him. Lay out your argument about the best candidate in this election, why it's a no-brainer. He's no dummy, so use condescending language or clichéd talking points at your own peril.

One last thing. At the end of one email, he listed the things most important to him this election cycle. This might be useful if you're going to make a persuasive argument. To quote: "1. Fixing the budget deficit. 2. Maintaining a viable and credible defense. 3. Maintaining the benefits that I paid for (Social Security, my pension). 4. Being able to get out from underneath my house [mortgage]."

Give it your best shot. I told him I was doing this. He'll be reading your comments.