I keep bumping into this thread searching Mudcat's calypsos so, what the hey… my two pennies worth:

MorwenEdhelwen1 & Ebbie's exchange about 'family-v-calypso' (above) is the closest to the truth though I'm pretty sure neither intended it that way. Marriage to a Trinidadian is/was her only option.

Any 'officially' recognized calypsonian has, in theory at least, the potential to be crowned "Calypso Monarch."

As such, one will remain the physical embodiment of the national Trinidad & Tobago calypsonian spirit until the following year's winner is announced.

Gibb: Why not poll the actual people who make calypso?

Close too but no polls. Read the Trinidad & Tobago United Calypsonian Organization Adjudication Handbook section on age and citizenship requirements.

After ruling the roost for the last twenty years they (TUCO) have recently been made subordinate to the larger National Carnival Commission (NCC) but culture and good old Yankee dollah tourism both depend that rule being there so I'm pretty sure it still is.