11/30/2008 05:12 am ET | Updated May 25, 2011

Red Relative Blues: Swinging Matthew's Cousin

Years ago I tried to "swing" my handsome friend Matthew, who I had a substantial crush on. He wasn't willing to go my way, but my heart fluttered just a bit when he said to me earlier this month "Ben! We have to swing my cousin. He's in Ohio." Woof! Then I realized he wasn't talking about that kind of swinging. He was talking about our Pinko Magazine/HuffPost's OffTheBus series highlighting efforts to swing our McCain-leaning or fence-sitting relatives around the country.

As we wrote here last week, Claire was trying to swing her grandmother. We have some news on that front, but you'll have to go over to Pinko for the results. Here at Off The Bus it's on to our new challenge: With 5 days to go, can we swing Matthew's cousin?

THE VOICE OF REASON: Matthew, 31, founder of a creative strategy and web/graphic design firm for non-profits based in Brooklyn.

THE NOT-YET-BELIEVER: Matthew's cousin Brian, 28, Cleveland, OH. Brian is married with a new baby, used to work for a Cancer-related non-profit and is a fan of socialist musicians like Bob Dylan and Paul Simon. He's the son of a carpenter. "He's not socially conservative," Matthew told me. "I enter this conversation knowing he's a good guy."

HOW IT CAME UP: Matthew noticed Brian joined the "Nobama '08" Facebook group. Putting aside the silly branding (is that the best they can do? Take the candidates name and put a "no" in front of it?) this was disconcerting to Matthew, especially given where Brian is voting next Tuesday.

THE CHALLENGE: Armed with the knowledge that his cousin was about to vote for endless war a candidate he didn't believe shared his values, how far is Matthew willing to go to convince a relative he doesn't speak with very often to change his vote?

THE APPROACH: Matthew went right after him, diving in with a respectful but direct Facebook message. Here's their first conversation:

matthew: "hey brian, are you really against the idea of Obama as president? just out of curiousity, why?"

CousinBrian: "He would certainly not be my candidate of choice... I am not a right wing nut-job who is all about the Republican party ... I'm strongly independent ... I don't believe the free market is the only answer, but I just cannot justify a society that mirrors the socialist politics of Western Europe. There needs to be a balance and Obama is way too left for me."

Matthew's initial response was sincere and earnest. ("I always cheer for the underdog," he wrote, "whether it's poor people, the Cleveland Indians, or John Cusak. I will always support whoever best represents working families.") The sports metaphor was a nice touch. The Say Anything reference was equally inspired. But Matthew hadn't addressed the "too left" argument directly or firmly enough. He needed another chance.

THE OPPORTUNITY: Two Sundays ago, Matthew got his opening.

CousinBrian: "Matt, I will say, Powell's endorsement of Obama has shifted my opinion some. I have great respect for that man, and have grown to hate Gov. Palin. With those two elements in mind, I now feel it is not right for me to campaign against Obama. As an independent, I am discouraged by both parties, but do not want to put myself in the libertarian or anarchist category. Tough place to be as an independent, even tougher when you have two candidates who represent their parties with total disregard for bipartisan common ground for the people. Convince me otherwise, I'm open minded."

THE DISCUSSION: Taking up his offer, Matthew made a detailed case to his cousin that Obama is no radical, no socialist, and sadly for us that he wouldn't turn the country into Sweden. (We will post the full emails over at Pinko. The exchange is long: this stuff is hard work.) He went especially hard on health care, writing that even if Obama wanted to revolutionize health care, Congress would water it down anyway. His goal was to assuage cousinBrian's fears. It was a depressing argument in some ways, arguing that Brian shouldn't fear Obama because Obama will ultimately disappoint the left, but it was honest and possibly true.

More inspiring was Matthew's defense of liberalism, and his challenge of Brian's notions of what socialism and capitalism really are.

"We don't live in a free market. We have private colleges that work well mixed with a huge system of state universities. Would we be better off without one or the other? Our economy balances market freedom with market regulation. It enables us to build airports and bridges that take us to National Parks and public beaches. The battle in Washington is not between capitalism and socialism, it's between slightly more public and slightly more private."

Still, Brian wasn't convinced. "You make some good points," he wrote, "and I do actually favor Obama's current approach to healthcare. But we'll see if he sticks to the plan he has proposed."

Brian's issue, then, isn't the issues. He's just sick of being lied to. He went on to tell Matthew that Obama is pushing "a utopia," raising hopes and making promises he can't keep.

"I would have respected Obama more if he had said, "look, we'll and do the best we can to protect you and balance the budget, but the government cannot help you live your life and bring happiness' Sure, that is political suicide, but that is who I would vote for. "I need a perfect mix of JFK and Regan! Scary thought, but both parties have lost their integrity."

THE VERDICT: Matthew made some final points about Sarah Palin and her readiness. He artfully brought up John McCain's significant chances of dying in office. But as of last weekend Cousin Brian remains moved but not yet swung:

Great points ...thank you. Very thoughtful and engaging conversation, I will take everything into account. I must admit, your arguments are the best non-biased and thought provoking I have heard yet. Most people just assume I have lost my marbles and have no soul!

Unfortunately the McCain campaign has launched an all-out barrage on Obama focused on the ridiculous "socialism" argument, and making a case that we need a "divided government." They have been speaking right into Brian's concerns about Obama. Have we lost ground?

WHAT NOW?: Matthew has made a strong case. He has been respectful and smart in a very difficult conversation. But 5 days out who is Brian voting for? Will the new attacks work? Is it appropriate for Matthew to go back in one more time and ask? If so, what arguments should he use? Matthew could reinforce his own support for Obama, or address the narrative of the past two weeks. Ohio, as that clever MoveOn ad tells us, could hang in the balance.

Leave your ideas and strategies in the comments, or email us: with "Swinging Grandma" in the subject-line. On Monday we'll report back on Matthew's progress. We'll also share some of your last weekend efforts to push friends and relatives off the fence. With early voting underway and the election so close are you calling it a day, or still working on that last undecided Aunt in Phoenix?