
Iván Calderón Pérez was a Puerto Rican professional baseball outfielder. He played in Major League Baseball (MLB) for four teams from 1984 to 1993, and was named an All-Star in 1991. Listed at 6 feet 1 inch (1.85 m) and 220 pounds (100 kg), he batted and threw right-handed. Nicknamed "Ivan the Terrible", Calderón was killed in a shooting in Puerto Rico in December 2003.

Héctor Luís Camacho Matías, commonly known by his nickname "Macho" Camacho, was a Puerto Rican professional boxer and entertainer. Known for his quickness in the ring and flamboyant style, Camacho competed professionally from 1980 to 2010, and was a world champion in three weight classes. He held the WBC super featherweight title from 1983 to 1984, the WBC lightweight title from 1985 to 1987, and the WBO junior welterweight title twice between 1989 and 1992.

Roberto Cofresí y Ramírez de Arellano, better known as El Pirata Cofresí, was a pirate from Puerto Rico. He was born into a noble family, but the political and economic difficulties faced by the island as a colony of the Spanish Empire during the Latin American wars of independence meant that his household was poor. Cofresí worked at sea from an early age which familiarized him with the region's geography, but it provided only a modest salary, and he eventually decided to abandon the sailor's life and became a pirate. He had previous links to land-based criminal activities, but the reason for Cofresí's change of vocation is unknown; historians speculate that he may have worked as a privateer aboard El Scipión, a ship owned by one of his cousins.

Kevin Fret was a Puerto Rican rapper, singer and the first openly gay male Latin trap artist. He was known for his gender-variant looks.

Miguel Fuentes Pinet was a Puerto Rican Major League Baseball (MLB) pitcher. Fuentes was signed to his first professional contract in 1969 with the Seattle Pilots. He went on to pitch in eight games for the club at the major league level after strong performances in the minor leagues. During the off-season, he was murdered in a bar fight at the age of 23.

Victor Alexis Rivera Santiago, better known by his stage name Lele “El Arma Secreta”, was a Puerto Rican rapper, singer, and songwriter signed to the Rottweilas label. He recorded solo or as part of a duo with partner Endo under Endo & Lele las Armas Secretas. He was also known by his nickname "El Arma Secreta".

Luis Ángel "Canena" Márquez Sánchez was a professional baseball player. He was the third Puerto Rican to play in Major League Baseball. Márquez played in a total of 68 games in the major leagues, split in two seasons between the Boston Braves, the Chicago Cubs and the Pittsburgh Pirates. His final game was on July 11, 1954.

Filiberto Ojeda Ríos was a Puerto Rican independence activist and militant who cofounded the Boricua Popular Army, also known as Los Macheteros, and its predecessor, the Fuerzas Armadas de Liberación Nacional Puertorriqueña (FALN). In 1990, Ojeda Ríos became a fugitive of the Federal Bureau of Investigation (FBI), wanted for his role in the 1983 Águila Blanca heist as well as a bail bond default on September 23 of that year. On September 23 2005, he was killed during an exchange of gunfire with FBI agents after they surrounded the house in Hormigueros, Puerto Rico.
The Ponce massacre was an event that took place on Palm Sunday, March 21, 1937, in Ponce, Puerto Rico, when a peaceful civilian march turned into a police shooting in which 19 civilians and two policemen were killed, and more than 200 civilians wounded. None of the civilians were armed and most of the dead were reportedly shot in their backs. The march had been organized by the Puerto Rican Nationalist Party to commemorate the abolition of slavery in Puerto Rico by the governing Spanish National Assembly in 1873, and to protest the U.S. government's imprisonment of the Party's leader, Pedro Albizu Campos, on sedition charges.

On October 14, 2019, six people were killed during a shootout between drug gangs in a gun battle at the Ernesto Ramos Antonini de Río Piedras residential apartments in the Río Piedras area of San Juan, Puerto Rico.