In 1997 there were a number of gang related attacked that left 14 people dead. The 14K triad under "Broken Tooth Koi" was being challenged by the smaller Soi Fong or Water Room triad.
The next year a gunman believed to be connected to the local 14K triad killed a Portuguese prison officer and wounded another at a sidewalk café.
Finally, in 1999, a Portuguese court convicted mob boss Wan Kuok-koi (45), aka "Broken Tooth" Koi, on various criminal charges and sentenced him to 15 years in jail. His 14K gang was suspected of drive-by shootings, car bombings and attempted assassinations. 7 associates received lesser sentences.
See also: Macau Security Force