1) I never had any kind of in-person discussion with him. The closest I came was during the Vietnam era, when he was making what he thought would be a routine visit to Harvard -- and to his enormous surprise was engulfed by seas of protestors who immobilized his car and yelled "Murderer!" at him. I was a newly arrived freshman and was walking down to sports practice when I found the street full of people and police surrounding a big black limo. Thirty years later, I ended up sitting next to McNamara on a DC subway car and decided not to say anything.
2) I know some of his relatives and in-laws. They loved and also respected him, and I am sorry for the loss of their father and grandfather.
3) In 1995, when McNamara published his In Retrospect memoir of the Vietnam War, I reacted very harshly in an NPR commentary. My argument was that he had missed his chance for a respectful hearing for his admission that the war in Vietnam was a mistake. If he hadn't done anything about that war when it could have made a difference, then there was no reason to, in effect, ask for public sympathy and understanding for his belated recognition of error. (Quotes after the jump.)
My tone then was harsher than I would be now. Perhaps that's just because I'm older; perhaps because McNamara has now died; perhaps because he had fifteen more years to be involved in worthy causes, mainly containing the risk of nuclear war or accident. But mainly I think it is because of Errol Morris' remarkable 2003 film The Fog of War, which portrayed McNamara as a combative and hyper-competitive man (in his 80s, he was still pointing out that he had been top of his elementary-school class) but as a person of moral seriousness who agonized not just about Vietnam but also the fire-bombing of Tokyo during World War II, which he had helped plans as a young defense analyst.