(I wrote this when the particular leadership controversy in question, the details of which are mostly mentioned in passing rather than described, was current. Bigger leadership controversies in FOSS have come to the fore since, but these questions remain.)
The title for this file is intentionally ambiguous, meant to evoke both the act of leading during a time of controversy as well as the act of leading into a situation of controversy.
There are a several points at which one could latch onto this discussion. To name just a few:
Whether or not the documentation should have been written to include in the first place the statement in question or not.
Once the statement was in the documentation, what reactions people had to it, and to what extent those reactions were immediately affecting based on personal experience and context, or anticipatory reactions on behalf of people with those experiences and contexts.
Once those interrogations of the text are given, whether or not to remove the statement in question from the documentation.
Once action to remove the statement in question has been taken, if and if so, how it is appropriate to revert the removal.
To the first question, if we ask what I would have done, I probably would not have included the 'joke' in the first place. That said, I tend much more to be a reader than a writer, which tendency I continue to work on overcoming (cf, this file). More to the point, I probably wouldn't have founded, much less pushed forward, something of the scope of the GNU project to begin with.
So, this brings the first point that seems relevant to me: People who create truly new things are, almost by definition and at least in some important ways, unconventional. This doesn't make flouting convention inherently creative, nor require all (small-c) creation to be accompanied by iconoclasm in every word and deed of the (small-c) creator. But, there is a connection.
Perhaps in some cases it comes from having, or cultivating, a certain naive view, a detachment, a lack of commitment to established norms:
This isn't to excuse 'bad behavior' so much as to wonder from whence it comes. Is there an irreducible link? Does the spotlight on these people bring our attention to foibles that might be prevalent, but unexplored, in others? Or, is there more of a drive to action in these people, which drive takes some paths we find laudable and some paths we find deplorable? Are these people more prone to sins of commission as compared to those of us whose sins of omission allow us to remain relatively anonymous in our passive virtue? Is this what even a small amount of power (even if just that that comes from fame or notoriety), or a lot of power even in a small community, tends to do to those without extraordinary abilities to resist?