President Obama's message to reluctant Wall Street donors is simple: Vote for me because I will win, and you want to be on the side of a winner. It's funny because that's the same message Mitt Romney, who made his fortune in private equity, had for Republican voters during the presidential primary -- that he was inevitable. In The New York Times Magazine, Nicholas Confessore writes a detailed account of how hard it's been for the Obama campaign to  cultivate Wall Street donors four years after they gave him $16 million, almost twice what they gave his opponent, Sen. John Mccain. But the story is also fascinating in the way it reveals how Wall Street people see themselves. It plays into the stereotype of Wall Street folks not being too particularly focused on principles.

Confessore writes:

“You call some people on Wall Street up, and they’re undecided,” one Obama bundler said. “They’re ‘waiting for clarity’ — that’s the term they use. Or they say the administration ‘hasn’t led sufficiently’ on an issue.” ...

Still, there were some factors working in Obama’s favor. The Republican primary — which forced Romney far to the right on issues like immigration and reproductive rights — had soured some Wall Streeters on his chances to win in November.

It's hard to read "clarity" as meaning something other than "poll numbers that show who's going to win." And this is the argument -- winning, not that "Obama has the best policies to save America from whatever" -- that the Obama campaign thinks is most likely to convince Wall Street people. Bundlers who host big fundraising dinners get weekly talking points for winning over reluctant givers, Confessore explains, like how to handle those who don't like the administration's policy toward Israel. "For those on Wall Street, however, the best argument boiled down to the simplest one: Obama was going to win," he writes.

The biggest hurdle appears to be hurt feelings. This seems to be in part because Wall Street is completely clueless as to how the rest of the country sees it. In a meeting with Obama campaign manager Jim Messina in late October, one suggested a speech on rich people along the lines of Obama's 2008 race speech. Really!

One of the guests raised his hand; he knew how to solve the problem. The president had won plaudits for his speech on race during the last campaign, the guest noted. It was a soaring address that acknowledged white resentment and urged national unity. What if Obama gave a similarly healing speech about class and inequality? What if he urged an end to attacks on the rich? Around the table, some people shook their heads in disbelief.

It goes without saying that the wealthiest Americans have not faced, over the course of American history, treatment that has much in common with the way black people have been treated over the course of American history. 

Wall Street's spat with Obama has been going on for months now. Back in September, Ted Leonsis, owner of some Washington sports franchises, wrote a widely-circulated blog post complaining, "It blows my mind when I am asked for money as a donation at the same time I am getting blasted as being a bad guy!" Leonsis didn't appear to have any disputes with Obama on specific policies -- he even said he'd already maxed out his personal donations to Obama's re-election campaign. But Leonsis was angry that Obama could attack a guy like him, who through hard work was fortunate enough to have "nice home with a housekeeper," when Obama has way more staff at the White House. The dispute wasn't about tax rates, it was about Obama not handing out gold stars. Since that post, Leonsis hasn't blogged much about politics, except to promote a favorable film about Occupy Wall Street. Maybe someone from the Obama campaign gave him a nice phone call?