Hello and welcome, Damon.
One thing I've long appreciated about the Wikimedia movement is that it is not political, and indeed the flagship project is explicitly neutral. This distinction has become a little more nuanced as the movement has taken political positions that are congruent with the overall mission, but I think it remains the case that Wikimedians have been able to avoid entanglements with general political issues. This has been especially the case with most deeply controversial and current political debates.
So while I agree with your sentiment, that leaders must model values such as courage and integrity, I think it would have been better expressed without the ringing endorsement of Che Guevara. As you say, we should choose our words carefully and ensure that our language is positive and inclusive. This is obviously an area where we can all make progress.
~Nathan