I said when I first brought up Douglass’ book that I didn’t agree with his ideas along those lines. So, you are preaching to the choir. However, Douglass does a good job of pointing out actions (and words) of JFK’s that do tend to show his character. JFK once described himself as “an idealist without illusions.” I take that to mean he was somewhat of a realist. What he wanted and intended to do wasn’t always feasible, and I believe that he knew that. He knew the horrors of war from his WWII experiences. He refused to get U.S. combat forces involved during the Bay of Pigs fiasco. He must have been deeply affected by the Cuban missile crisis. Who wouldn’t be after being in his position? He used secret back channels to work out his deal on the Cuban missile crisis. He (after a flurry of testing by the U.S.) worked out a deal on a limited test ban treaty. There is evidence that he was using secret back channels to try to normalize relations with Cuba. The RFK demands for more action against Cuba might have been a tactic designed to give Castro an incentive. Who knows?
Right, I never got the idea that you believed in Douglass's main claim, i.e., that JFK was going or wanted to toss out the containment/Cold War policies against the communists and that he only supported them because he was forced to by the MIC/Pentagon/CIA. Who then, according to Douglass, killed him because he was going to do just that. Saying JFK wanted to "calm" relations down with Moscow, normalize the relationship as he said in the AU speech or that he tried to probe for or find a peaceful settlement of conflicts is one thing; claiming that he didn't fundamentally believe in the necessity of containment, as Douglass appears to do, is another. And as for killing JFK: sorry, one lost angry person with a cheap rifle did that. It didn't require an army of conspirators.
In his book on the Kennedy presidency, the historian Richard Reeves mentions how the Kennedys, especially JFK, liked using back channels and promoting a two track policy. That is, negotiate and pressure, pressure and negotiate. Lots of presidents have used back channel communications but JFK seemed particularly interested in using them. During the crisis with Moscow, with Castro and others. JFK really did show an intellectual independence from his advisers - from the military in particular - that led to his probing and questioning policy. We saw this most obviously in the missile crisis. I think on Vietnam he would certainly have been more willing to ignore the "Best and Brightest" than LBJ did (in one of his letters he sent from the Pacific during the war he complained: "The military fucks up everything."). Would he escaped the trap that McNamara mentioned above? We can only guess.
It's interesting that JFK's legacy - who he was - is probably fought over more than any other president. Conservatives like to say he'd be one of theirs - tax cuts, anti-communism, et cetera - while liberals say his civil rights policies and American University speech shows he belonged to them. He really did defy an easy description or characterization. He was pragmatic but idealistic; cautious but open minded. Some of the qualities of the right and left.
Douglass' claims aren't all wrong but I think to portray JFK as some critic of containment is just flat out wrong. He may not have been a hawk - as defined by the period - but he wasn't a dove either. He was probably what political scientists called an "owl." Owls believe "the greatest risks of such war come from events getting out of control." I think JFK was terribly worried about that, about events escalating into a direct US/Soviet conflict.
On the Cuba policy: I think they took Castro personally. They wanted him dead or certainly out of power (which almost certainly required is death). JFK reportedly thought that they could turn Castro into a Tito, that is an independent communist. I think they knew otherwise; that he was a lost cause. After going over the Cuban policy the evidence I read shows that a lot more of the covert attacks than I realized continued after JFK's death. RFK pushed most of it but it didn't all go away after 11/22/63.