To be honest 'yuh have to be ah Trini to quickly grasp this one'. In the end you will realize that when "yuh dig horrors', Trini style, it makes you feel the Caribbean flavor that makes one yearn to return to the homeland not 'to dig horrors' but to soak up some of this very special culture that paints these 'Trinididioms' in our hearts and minds forever.
To dig for something connotes a search for something; like to dig for yam or plough the land to plant (yuh dig up d'ground to ensure that the soil is turned and growth is possible in loose soil). Hmm, sounds like a plan right - wrong! When someone, especially a Trini is 'digging horrors' then something is very wrong - life is not the same and we are very upset about something.
Trinis dig horrors when they are vexed or simply confused and stressed. Take the instance of the young man who is in love with this young lady only to find out that she is 'creeping' with his best friend; you guessed it, this Trini begins to dig horrors as he falls into a tabanka pit - horn eh nice nah!
Another case is that of another young man who just got pay but because he thinks he is smarter than the hustler on the block starts to gamble playing brag or knock rummy (terms confusing?) and he loses his pay check. This 'is pain' as 'they say' [and they are always saying (as in complaining) in Trini land] lately and the family definitely with be "diggin' horrors" because someone else was smarter that Mr. Chupidee - time to start "diggin' horrors"
There you have it, "ah diggin' horrors" is simply a case of severe stress, pain, frustration that does not seem to have a feasible ending. The situation is one of distress fraught with anger and disappointment. Having said that we can now take a listen of a remake of Sparrows classic "Ah digging horrors" done by RemBunction with cameo performances by Roy Cape and the bard himself Slinger Francisco aka Mighty Sparrow, calypso king of the World.