Over at Cross-Currents, Rabbi Yaakov Menken sets out some comments about this. Twenty years ago, I would have agreed with his words whole-heartedly, and in fact I published similar ideas to his. However, since then, my understanding of this topic has evolved. I attempted to respond to his claims in the comments section to his post, but he did not post my comments, for reasons that are unclear to me. Fortunately, I have my own forum for responding, and so I am posting my response here instead.
Rabbi Menken begins with the following claim:
"A big part of Judaism is learning to nullify our will to Hashem’s will. The leaders of our nation have always been the people who did this best — who learned Torah and let it guide them, rather than trying to superimpose their own values on the Torah."This claim is very prevalent in charedi circles. The simplest and most powerful way to rebut it is that none other than the Vilna Gaon clearly disagreed. After all, he said that Rambam - certainly a leader of the nation - was negatively influenced by Greco-Muslim values.
Ardent follower of Rambam as I am, I would nonetheless agree with the Vilna Gaon that Rambam was influenced by Greco-Muslim values. However, I would say that this was largely (though not entirely) positive. And the Vilna Gaon himself was also influenced by non-Divine sources. No man is an island.
Rabbi Menken then argues that while all humans, including Rabbonim, can err, we have to follow Rabbonim because "(a) the Torah tells us to and (b) They still know better than we do." This oversimplifies a very complex topic. Yes, there is certainly an important idea in Judaism of following rabbinic leadership, but not every great rabbi has the stature of the Sanhedrin. Furthermore, which Rabbonim is one obligated to follows? The Chassidim or the Litvaks? The Charedim or the Religious Zionists?
Finally, we come to a very significant and problematic claim:
"One thing that certainly cannot be done is to try to second-guess them based upon an alternate reality that never happened — e.g. saying that “the Holocaust” somehow proves Rabbonim were wrong telling people not to leave Europe. If we look at Jewish history, it happens repeatedly: appearances are deceiving. What appears to be is not the reality — which is really about where we stand with HaShem... It is well-known that people who left Europe before the war had tremendous difficulty keeping their level of observance."Now it is indeed true that we cannot claim that we would have made any better decisions in those circumstances. It's all very well to have hindsight about what happened in the Holocaust, but who is to say that had we been there, we would have known what to expect and what to do? That is why we cannot look down on the decisions of anyone in that period.
However, we can certainly observe that those Gedolim who urged their followers to stay in Europe made a tragic mistake. The Belzer Rebbe, for example, told his followers in Budapest that they will enjoy good and tranquility in Hungary. They were all sent to Auschwitz. Yes, maybe up in Shamayim that is somehow all for the best, but down here that is what we call a tragic mistake. It is certainly not for us to say that leaving Jewish observance is worse than being massacred by the Nazis, and therefore those rabbonim who led their followers to the latter did the right thing. In fact such a sentiment is deeply repugnant, like someone making the berachah of hatov ve-ha-meitiv on the passing of a loved one.
There are clearly many Rabbonim who disagree with the notion that, since we do not know the ways of Heaven, we cannot criticize the actions of Gedolim. See, for example, R. Teichtal's Em Habanim Semecha. See too Rav Aharon Lichtenstein's famous address where, quoting Rav Hutner, he points out that Chazal clearly held that one can be a great talmid chacham and yet lack da'as. All the more so one can be a great talmid chacham and make mistakes, and there is no reason to think that other people are incapable of observing this. The Holocaust is a powerful and tragic example where, without judging the culpability of the Gedolim who advised their followers to stay in Europe, we can clearly observe that they were tragically mistaken.