Legendary status is relative...
Legend implies that you will "forever" be renowned and remembered. A legend's reputation transcends time and generations.
Call me harsh, but there are currently no Trinidad players that absolutely fit that bill outside of Trinidad...
Latapy ? Arguably at Falkirk & Hibs...
Yorke ? Arguably at Man U or Villa....and only barely
Will Dwight Yorke Man U or Villa shirts & Posters be hot selling items 20 years from now ? maybe, maybe not....
The thing about it is, legendary status is not attained mererly by merit and ability, and it often takes something other than extraordinary ability to propel an individual into legendary status- eg..a crucial goal when the stakes were highest -(Kerry Jamerson is arguably a local legend), a memorable celebration ,a career comeback in the face of adversity, a tragic accident, a long career at one particular club/club loyalty, maintenance of good form at an old age (Latapy at Falkirk), a highly controversial or eccentric personality, humanitarian efforts outside of the game,.....or sometimes just the right amount of hype- believe it or not, David Beckham is probably already a footballing legend both in Manchester and world wide.....
Latapy & Yorke (and others) are without a doubt local (In T&T) footballing legends. I wouldn't yet venture to go any further than that.