use of word, "pretender"

I have a question about the meaning, especially the connotations, of the word,
"pretender." I know what my dictionary says, but I'd like to have a better feel
for how it's used and what it implies. To me, one connotation is derogatory and
the other is not. For example,

If a person would have been the next monarch, had their monarchy had not been
overthrown, I see no reason to necessarily hold the person in contempt, but if
someone affects a position or title -- or usurps such a title -- to which they
were never rightfully eligible, I view that as contemptible.

Would the term, "pretender," apply to both, or to only the former?

Chris Dickinson...

I don't think you can make it as simple as that. Nor is it fair to make
moral judgements on those involved.

The classic case of the use of 'Pretender' is out of this period and refers
(Old and Young) to the Jacobite heirs to the English and Scottish thrones,
James and Charles (Bonnie Prince Charlie).

From a progressive perspective they were pretenders, and had no right
whatsoever to the throne - the basic principle being established was that
Parliament decided the succession, not Blood; but from their perspective,
they had every entitlement.

[What does annoy me is non-Brits who still refer today to the Old Pretender
as James III, akin (if at least harmless) to the 20th century funding of the
IRA]

One of the simple facts of politics is that people and countries make
titular claim to things that they have no practical control over, with
varying degrees of theoretical justification and of political manipulation.
I don't think that one can make moral judgements about this - at what point
did the English monarch's claim to be King of France become contemptible?

This happens at all levels. It happens, for instance, at manorial and parish
level where boundaries are unclear; and the entitlement to fines, rents and
the like are in dispute. The same sort of thing happens between properties
over responsibility for boundary walls!.

But, going back to your original comment, I would think that the use of the
term 'Pretender' is always derogatory. It is used from the perspective of
the person, group, political body, culture that HAS - the party that HASN'T
would use another term like 'rightful king'.