So, I’m not even sure if it’s Bulgarian, but it seems it’s the order of Saint Alexander (6th grade).
I still wonder what is the date on the reverse, because it’s three years before the order was first created according to Wikipedia (Polish, English and Bulagrian) and I couldn’t find anything about the date 19 February, maybe it is the birthday of my grandfather?
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your relative should have been an important person, the date is from the San Stefano treaty signing. Possibly awarded by Tsar Ferdinand as this is his monogram
edit: was your relative part of the Bulgarian army at some point? or maybe a western missionary? Ferdinand reigned between 1909 and 1918, so possibly as you seem to be a German this could be from first world war as we were allies at this time
edit2: do you have the certificate of issue?
Order of Saint Alexander [Wikipedia](https://en.wikipedia.org/wiki/Order_of_Saint_Alexander)
Its an order given to you by order of the monarch himself,so your grandfather was probably really popular or important to recieve it.(Probably by showing immense courage or skill fighting the turks).
6th grade/level order of Saint Aleksandr. the medal says “God is with us” on one side and the other “19th of february 1878”. Note that Aleksandr is written in russian, so it was probably given by Russia for fighting in the liberation war, since 19/02/1878 is when the peace treaty was signed
What was his name? This is considered a collectable item in Bulgaria.
https://bazar.bg/obiavi?q=%D0%BE%D1%80%D0%B4%D0%B5%D0%BD%20%D1%81%D0%B2.%D0%B0%D0%BB%D0%B5%D0%BA%D1%81%D0%B0%D0%BD%D0%B4%D1%8A%D1%80
19th of Ferbuary 1878 was the old date of the signing of the San Steafno treaty which was the end of the Russo Turkish war:
https://en.wikipedia.org/wiki/Treaty_of_San_Stefano
https://bg.wikipedia.org/wiki/%D0%9D%D0%BE%D1%81%D0%B8%D1%82%D0%B5%D0%BB%D0%B8_%D0%BD%D0%B0_%D0%BE%D1%80%D0%B4%D0%B5%D0%BD_%E2%80%9E%D0%A1%D0%B2%D0%B5%D1%82%D0%B8_%D0%90%D0%BB%D0%B5%D0%BA%D1%81%D0%B0%D0%BD%D0%B4%D1%8A%D1%80%E2%80%9C_%D1%88%D0%B5%D1%81%D1%82%D0%B0_%D1%81%D1%82%D0%B5%D0%BF%D0%B5%D0%BD
There is a list of people with the medal, any of the names sound familiar?
It was awarded for civil service in time of war, so most probably the Balkan wars or WWI. My great-great-grandfather was awarded one (VI and then V grade) for working as a teacher in occupied Măcin, Romania, during WWI. (I’m kind of suspicious).
Your ancestor was most probably awarded for performing his duty as a public servant during a war.