Generalissimo
/ˌdʒenrəˈlɪsɪməʊ/
Definition 1 of 1
Pro Tip 1/3Historical Usage
The term often relates to historical leaders more than current ones. 
The term 'generalissimo' reminds me of figures like General Franco.
Pro Tip 2/3Not Common
'Generalissimo' is rarely used in everyday conversation; more in historical context. 
Outside history class, you won't hear 'generalissimo' much.
Pro Tip 3/3Cultural Connotation
Can imply absolute power or a dictatorial stance when used to describe a leader. 
The dictator styled himself as the 'generalissimo' of the nation.
Compare with
AutocratDictatorLeader
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