not my proudest ( which would of been going from a count to a king in Ireland for the first time. (I have done a lot more since then, but i was darn proud the first time i did that.)
but the moment that my family thought I had gone nuts was that my family did the reconquista in a long lifetime. (Note to self, marry a good brother to a princess of the HRE, then give him a kingdom, he and the HRE will do a lot of the legwork.)
The Kingdom of Galicia was in easy control of a cedet branch of my family, the main branch controls Granada, I gave Seville to the knights of St. John (which turned out to be a brilliant move, as they keep the North Africans from easy assaults into Iberia. ) Castile adsorbed Leon (but is of my family due to marriage and a unfortunate death of the heir (oops), the rest of the Christian kingdoms had done nothing, Barcelona went Barcelona -> Muslim -> French -> Danish (don't ask), and Navarre is a basketcase)
The rest of Iberia is the Kingdom of Protugul, which has expanded like Prussia and goes from Sea to sea, and has taken a chunk of North Africa too, lead by the very able 74 year old Legitimized bastard who was a brother to the grandfather of my current ruler. He had 9 kids, the only male dying at 17 due to illness. For the last two generations the main line has been looking on rooting for a Male Heir to keep it in the family. A specific chaste wife fell off a roof and another one who got old found a viper. then at age 74, with is north African wife, he produces a son.
As soon as i saw that I shouted "Its a miracle!!!" loudly since i had earphones on.
My family thought I had lost it.
Now lets hope this guy can make it in his 90s so his son can be almost a adult when he takes over his kingdom, which will be one of the more powerful ones west of the HRE once I divest of my crusader state.