Well actually, bastards of the powerful men could quite well even in the presence of legitimate heirs. Sons could get titles, daughters could marry advantageously (ex: Katerina Sforza Riario). For example, Kind Ferrante of Naples was a bastard who got a piece of his father Mediterranean empire. Rodrigo's predecessor Pope Innocent had two illegitimate children (born before he became a priest so it wasn't a big deal). The son got lands and money (he's featured in S1 of the other Borgia show). Lucrezia's husband Alfonso d'Este conferred a title on his bastard. It seems that Italy especially was fairly lenient with bastards vs. other countries (but even there, the only thing that was barred from bastards was the crown).
Any medieval leader with sovereign power (i.e, the ability to make law) could make his/her children pretty much whatever they pleased and bastards could certainly inherit property--if the parent in question desired to do it.
A classic case of this is William the Conqueror, who began life as a bastard and was made the Count of Normandy at the age of seven--after previously growing up in a small village as basically a peasant. He wasn't even the first illegitimate count in the line.
Also of great interest on this subject are the origins of the Kingdom of Portugal as they relate to the rivalry between illegitimate Countess Theresa of Portugal and her legitimate sister, Queen Regnant Urraca of Castile. Urraca herself had illegitimate daughters by one of her nobles after two marriages gained her a male heir, and ended in widowhood and acrimonious divorce, respectively.
People too often look at the flashy and megalomaniacal rule of Henry VIII of England and see it as the way things normally were in the Middle Ages. Even if the bulk of Henry's rule were not, in fact, in the Reformation not the Middle Ages, and there were any such thing as a general rule of thumb for that extremely large and diverse period, there would be nothing "normal" about Henry's rule. His reign was laced with discontinuity from previous tradition, from the death of his brother (the original heir) to his decision to join the Reformation and become head of his own church, to the stripping of the altars, to his really peculiar way of dealing with his wives, when he already had a legitimate heir (two, if he'd stopped at Anne).
Yes, there were extra challenges for a ruling queen, but, as Henry's daughters demonstrated after his death, they were quite equal to them. He was a pretty awful ruler with a frightening level of tunnel vision that disrupted his reign permanently. It's not as though other rulers before him hadn't dealt with the issue far better.
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