Betty Lu Saltzman, a Democratic doyenne from Chicago’s lakefront liberal crowd, convened a small group of activists, including Ms. Katz, in her living room to organize a rally to protest the United States’ impending invasion of Iraq. It was late September 2002, and Mr. Obama was on the top of Ms. Saltzman’s list of desired speakers.

She first met him when he ran the black voter registration drive in the 1992 election, and was so impressed that she immediately took him under her wing, introducing him to wealthy donors and talking him up to friends like Mr. Axelrod. But with just a few days to go before the rally, Ms. Saltzman was having trouble reaching Mr. Obama. Finally, she said she left word with his wife.

But before Mr. Obama called her back, he dialed up some advice.

With his possible run for the United States Senate, he wanted to speak with Mr. Axelrod and others about the ramifications of broadcasting his reservations about a war the public was fast getting behind. An antiwar speech would play to his Chicago liberal base, and could help him in what was expected to be a hotly contested primary, they told him, but it also could hurt him in the general election.

“This was a call to assess just how risky was this,” said Pete Giangreco, who along with Mr. Axelrod described the conversation. When Mr. Obama tossed out the idea of calling it a “dumb war,” Mr. Giangreco said he cringed. “I remember thinking, ‘this puts us in the weak defense category, doesn’t it?’ ”

The rally was held on Oct. 2, 2002, in Federal Plaza before nearly 2,000 people. On the podium before speaking, Mr. Obama joked about the dated nature of crowd-pleasing protest songs like “Give Peace a Chance.” “ ‘Can’t they play something else?’ ” Ms. Saltzman recalled his saying.

The speech, friends say, was vintage Obama, a bold but nuanced message that has become the touchstone of his presidential campaign: While he said the Iraq war would lead to “an occupation of undetermined length with undetermined costs and undetermined consequences,” he was also careful to emphasize that there were times when military intervention was necessary.

“What’s fascinating about Barack is what he’s trying to do is reframe and change the discourse so you build support for liberal alternatives within the electorate,” said Will Burns, a former aide whom Mr. Obama also consulted on the speech. “He has an ability to frame stuff so it’s not an all or nothing proposition.”

Still, Mr. Obama’s refrain about supporting some wars perplexed some in the crowd.

An event organizer, Carl Davidson, recalled that a friend “nudged me and said, ‘Who does he think this speech is for? It’s not for this crowd.’ I thought, ‘This guy’s got bigger fish to fry.’ At the time, though, I was only thinking about the U.S. Senate.”

[…] For years, the Obamas had been regular dinner guests at the Hyde Park home of Rashid Khalidi, a Middle East scholar at the University of Chicago and an adviser to the Palestinian delegation to the 1990s peace talks. Mr. Khalidi said the talk would often turn to the Middle East, and he talked with Mr. Obama about issues like living conditions in the occupied territories. In 2000, the Khalidis held a fund-raiser for Mr. Obama during his Congressional campaign. Both Mr. Khalidi and Mr. Abunimah, of the Electronic Intifada, said Mr. Obama had spoken at the fund-raiser and had called for the United States to adopt a more “evenhanded approach” to the Palestinian-Israel conflict.

Still, Mr. Khalidi said ascertaining Mr. Obama’s precise position was often difficult. “You may come away thinking, ‘Wow, he agrees with me,’ ” he said. “But later, when you get home and think about it, you are not sure.”

A.J. Wolf, a Hyde Park rabbi who is a friend of Mr. Obama’s and has often invited Mr. Khalidi to speak at his synagogue, said Mr. Obama had disappointed him by not being more assertive about the need for both Israel and the Palestinians to move toward peace. “He’s played all those notes right for the Israel lobby,” said Mr. Wolf, who is sometimes critical of Israel.

During the Senate campaign, Mr. Obama joined in a “Walk for Israel” rally along Lake Michigan on Israel Solidarity Day. The Crowns and other Jewish leaders raised hundreds of thousands of dollars for him. Several days before the primary in 2004, some of his Jewish supporters took offense that Mr. Obama had not taken the opportunity on a campaign questionnaire to denounce Yasir Arafat, the leader of the Palestine Liberation Organization, or to strongly support Israel’s building of a security fence.

But in a sign of how far Mr. Obama had come in his coalition-building, friends from the American Israel Political Action Committee, the national pro-Israel lobbying group, helped him rush out a response to smooth over the flap.

In an e-mail message, Mr. Obama blamed a staff member for the oversight, and expressed the hope that “none of this has raised any questions on your part regarding my fundamental commitment to Israel’s security.” Mr. Abunimah has written of running into the candidate around that time and has said that Mr. Obama told him: “I’m sorry I haven’t said more about Palestine right now, but we are in a tough primary race. I’m hoping that when things calm down I can be more upfront.”

The Obama camp has denied Mr. Abunimah’s account. Mr. Khalidi, who is now the director of the Middle East Institute at Columbia University, said, “I’m unhappy about the positions he’s taken, but I can’t say I’m terribly disappointed.” He added: “People think he’s a saint. He’s not. He’s a politician.”

While on one hand, you might occasionally be depressed about that, you could also tell yourself, “Wow, what incredibly expressive, passionate and articulate offspring I’ve raised! I’m so glad I put such effort into stimulating their intellects!” It might help, you never know.

It can be an upward slog as they get older, because you eventually find it more difficult to keep a sense of humor about these things. Whereas once I would say brightly, “I’m so glad to hear you attack me like that, because at this stage of your emotional and psychological development, you should be rebelling against my values and this means I’ve done a really good job raising you!”, now I just say, “I’m sorry.” Because I am. (And then I think to myself, “You’ll just have to take that up with your therapist, since I don’t have access to a time machine and can’t undo the past.”)

My kids were truly delightful children whose presence brought me much joy, pretty much until the moment they moved out and went to college. Okay, there was that adolescent phase where they were beating the crap out of each other so much, I dragged them off to a family counselor to see if it was “normal” (the oldest sat there and refused to say anything the entire time), but they eventually got to the point where they could go weeks at a time without physically attacking each other, and that made me happy.

They had a lot of seething hostility toward their father, and when he died a few years ago, there was a rapid and seamless transition of all that anger over to me. (Which was a bit of a shock, even though I expected it. I used to tell them they only idealized me because they compared me to their father, that I was just a normal human being with lots of human failings. Apparently I convinced them.)

Anyway, they’re adults now. They like me sometimes but more often than not, they don’t. Most interactions (although not all) come with exasperated sighs, much eyerolling and at least a short list of my shortcomings, and that can be depressing. (My male friends tell me not to worry: “I hated my mother at that age, too,” and advise me they really won’t understand until they have kids of their own, since that’s what made them realize their own mothers really weren’t in the Bad Mothers Hall of Fame.)

But I digress. The fact is, there are many things I might have done differently, but they’re things I couldn’t possibly have done any differently, given those particular circumstances. That’s the bitch of it - middle age is when you realize that just about everyone would have made better choices, but they didn’t know how. You can’t make someone see when they’re blind, after all, and being angry at them for not seeing is wasted time and energy.

Like every mother, I only did the best I could at the time. (Sometimes I just fucked up, plain and simple. But I never set out to do it.)

This is not to say I regret having my kids, because I don’t. It’s only that nothing really prepares you for being a mother, and no one ever really warns you about the eternal burden of guilt you’ll carry. You can’t read your way into that understanding, you can’t train for it.

That’s why I try to do what I can for the young mothers I know. I listen, I offer to babysit, I encourage them to take some time to take care of themselves. “They’re going to blame you for everything anyway, so there’s no point to killing yourself,” I tell them. Motherhood is full of lonely moments where you wonder why all those other mothers seems so utterly thrilled to be making three dozen cupcakes from scratch after a long, long day, and here is my answer: Those women are pretending. Those are the kind of women who end up drowning their babies in the bathtub while their husbands are away on extended business trips. They pretend, and finally something snaps.

Don’t be one of those women. If you’re not pretending, you’re in a much healthier place. I’m of the Roseanne Barr school of motherhood (only without the multiple personalities): “If he comes home at five o’clock and those kids are still alive, I’ve done my job.”

So if you’re a mother, today I salute you. (If you’re my mother, I also take you out for brunch.) And if you’re a father (barring, you know, heroin addiction or the aforementioned psychosis on the part of your wife), you should fall down on your knees and kiss her very toes. Because you really have no idea.

And then you should take the kids out of the house for the entire day, before you come home and cook dinner.

Admittedly, this is the kind of counterfactual that’s impossible to prove, but my guess is that if she had voted against the war Clinton would be the Democratic candidate. Given the closeness of the race, her inherent advantages going in, and that the war had to be a liability it’s hard to imagine that she wouldn’t have prevailed without the Iraq albatross. Whether or not Clinton’s support was sincere — I don’t think it really matters — sometimes getting big policies wrong really is politically damaging. (See also the 2006 midterms.) This is evidently a good thing.

I don’t know how typical I am of people who voted for Obama, but I went into the primary not even considering anybody who voted for the war. Obviously that ruled out just about everybody except for Richardson and Obama. Oh, and Kucinich, but I have other reasons for not supporting him which are too boring to write about right now.

I generally favor Clinton’s approach to Obama’s on most of the issues, though I think they’re both entirely too tepid on nearly everything. Had she not voted for the authorization to use force, I almost certainly would have supported her. I don’t know how many people there are like me, but I suspect that in an election this tight and with the proportional system allowing small shifts to make a significant difference, that there were enough of us to have caused a problem for Clinton.