Can’t Buy Mayor? Donate.

Today we’re looking at the genuinely complex issue of whether private charities closely connected to City Hall constitute a back door to influence. In particular, we’re reporting that some administration critics see Dan Doctoroff standing too close to NYC2012, and that some lobbyists believe donations to the Olympic bid are good for their clients’ business with the city.

Said one of these lobbyists: “If a client came to me and said ‘Look, I want to get in with this administration,’ I’d say, ‘Hey, give to the Olympics.’”

The main news in the piece is that the Campaign Finance Board is interested in the question too. Also, don’t miss the fact that Dan has a special exemption from the Conflicts of Interest Board to raise money for the Olympics.

But we want to stress that there’s no evidence that Dan has been influenced. “There’s no smoke,” his friend Jay Kriegel told us in disgust.

That’s why this “pay-to-play” stuff, as the Mayor calls it, is such tricky ground in the first place. Bribery is against the law. Some arrangements that are legal also look quite bad: when real estate money flows to the campaign of a Council Member with a say on a zoning exemption, for example. But there’s often no way to prove a quid pro quo without climbing inside the politician’s skull. And beyond the obvious sleaze is a vast gray area, and that’s where we find the private charities connected to the Bloomberg administration — the Republic National Convention‘s Host Committee; the Fund to Advance New York City; and NYC2012. And at the very least, NYC2012′s list of contributors is packed with companies doing business with, or regulated by, the city.

We’d only add two factors that make these questions more salient: that Bloomberg has set himself a high standard by leading a (worthy) crusade against “pay-to-play”; and that since the mayor doesn’t take political contributions, charitable donations could serve as an expensive substitute.

(And we’ll also confess here to a misstep that we’re hoping not to repeat. When a recent Daily News story about the Mayor’s Fund really got us thinking about this issue, we, like the novices we are, went and tipped our hand on the damn blog!)