On this date in 1999, crime lord Dole Chadee hanged at the prison in Port of Spain, capital of Trinidad and Tobago … to be swiftly followed by two members of his narco-trafficking syndicate, with six more of their number set to die over the succeeding 72 hours.

A big-time mover of cocaine and therefore a big man in the former British colony, Chadee — “Nankissoon Boodram” to his parents — was recognizable for a generation for his slick coiffure, mirrored shades, and greased-palm untouchability.

He greased plenty of people, too.

Maybe it was only consequence of losing the traffic’s underground turf war that made the fatal crimes politically possible to prosecute. Whatever it was, the murder outraged of a small-time cog in his network — and the cog’s sister — and their parents — outraged a public weary of rampant drug violence.

So most of his countrymen were pleased to see Chadee swing, and little wonder: this hombre was bad enough to get the chief witness against him assassinated while behind prison walls.

In fact, Chadee led an active life in the criminal underworld from the shadow of the gallows. Chadee’s own brother was kidnapped for ransom in a gangland tit-for-tat episode while the boss awaited the rope. Dole Chadee refused to have it paid, and the brother was murdered.

And there was family drama on the other side of the legal briefs, too.

The hangings were secured by the aggressive action of Attorney General — and former anti-death penalty lawyer — Ramesh Maharaj. During the very time he was getting the noose around Dole Chadee’s neck, Maharaj’s own brother was on death row in Florida (the sentence has since been reduced to life imprisonment).

There were fears (or hopes!) that the Caribbean island’s breakthrough executions could open the floodgates for “hundreds” held up by legal rigmarole and the picky oversight (pdf) of the British Privy Council. Another hanging followed that of Chadee’s gang a few weeks later. But since then … nothing.

On this day..

• 1571: Sigismondo Arquer, Sardinian scholar
• 1951: Sandor Szucs, Hungarian footballer
• 1718: A horse thief and two travelers, "the worst rideing that ever I rid"
• 1886: A day in the death penalty around the U.S. South
• 1867: Gottlieb Williams, eyeballed
• 1886: Tabby Banks and Tom Honesty, for election rejection
• 1155: Arnold of Brescia
• 1937: Helmut Hirsch, secret bomber
• 2008: Curtis Osborne, poorly represented
• 1516 and 1530: Autos de fe in the Spanish Canary Islands
• 1814: Four of five deserters, in Buffalo
• 1913: Antonio Echazarreta, defending Matamoros