Esteban Calderone

Esteban Calderone
Affiliation	Leader, Calderone Drug Cartel
Born/Died	1940-1984
Status	Deceased, shot by James "Sonny" Crockett
Relatives	Orlando Calderone (son) Angelina Madeira (daughter) One grandchild
Episode(s)	"Brother's Keeper" "Calderone's Return (Part II)"
Played By	Miguel Piñero

Esteban Orlando Calderone (1940-1984) was the leader of the Calderone Drug Cartel, which ran from the Bahamas to Miami to New York and other unspecified locations. He was killed by Metro-Dade Vice Detective James "Sonny" Crockett to prevent him from killing Ricardo "Rico" Tubbs at Calderone's palatial home on St. Andrews Island.

Early Life

Not much is known about Calderone's early life, except he never got past fourth grade in school. He began his drug empire around 1966 (per the DEA files on him) and was wanted by numerous law enforcement agencies, including FBI, ATF, DEA, Metro-Dade, and others, but Calderone was able to escape prosecution by using his considerable wealth (accumulated from years of drug activity) to buy off anyone, including police officers, attorneys, judges, clerks, etc. to ensure his empire was untouched.

New York/Miami Activities

In 1984, Calderone was running drugs to New York, and he caught the attention of NYPD Detective Rafael Tubbs, who began working undercover to bring him down, but he and his partner Tooney were killed by Calderone's men in a drug deal gone sour. Tubbs' brother Ricardo was angered by the killing of his brother and mentor, and went to Miami to locate the drug lord and avenge his brother's death, using forged NYPD priority clearance documents to get the help of the Metro-Dade police. Tubbs and his new partner, Metro-Dade detective James "Sonny" Crockett, was able to meet Calderone through his lieutenant, Trini DeSoto, and arrange a drug deal, but Tubbs was exposed by a Calderone informant, DEA agent Scottie Wheeler, and Calderone sent DeSoto to kill the NYPD officer, but Tubbs was saved by Crockett and DeSoto was killed. The deal went through, and all of Calderone's men were killed, and the drug lord was staring down a shotgun held by Tubbs, who decided not to pull the trigger and let the justice system take care of him. But before Calderone could be transferred to an unknown location, he was able to contact a judge to have him sprung from jail and escaped in a seaplane before Crockett and Tubbs could bring him back.

Calderone Returns

One month later, Calderone began to eliminate competition in the Miami area, and hired professional hitman Ludovici Armstrong to kill eight people on a hit list, including seven dealers who no longer got their product from Calderone, and the policeman who busted him, Crockett. With his "handler", Carlos Mendez, Armstrong managed to kill the seven dealers, but Crockett eluded the hitman's bullet, Armstrong was killed by a phalanx of police, and Mendez was arrested. Under intense pressure, Mendez divulged that Calderone had relocated to the Bahamas, specifically St. Andrews Island. Crockett and Tubbs pursued the drug lord to the island, where Tubbs encountered Angelina Madeira, who was seen going to Calderone's yacht, though the local police chief, Albury, denied Calderone was there. Later Calderone paid Crockett (under the guise of Armstrong) for his hit list, but Crockett wanted more money and to see Calderone in person or the drug lord would be the next person killed. Calderone's response was to send four shooters out to kill Crockett and Tubbs, but they failed, and the detectives concluded Albury was in Calderone's back pocket. Tubbs went to see Angelina to find out where Calderone was and they slept together (which resulted in Calderone's grandson, Ricardo, being born in 1985), after which Tubbs found Angelina was Calderone's daughter, and they attended a masquerade party that night. At the party Calderone's men took Crockett away at gunpoint, Tubbs and Angelina went to Calderone's house and found Crockett being held by three of Calderone's men.

Death/Vengeance

Crockett used an opening to gain a machine gun and proceeded to beat up two of Calderone's men with it, then the third man shot at Tubbs, who returned fire. Just as Calderone raised his gun to shoot Tubbs, Crockett emptied the machine gun's entire magazine into Calderone, killing him, and his lifeless body fell into his pool.

After Calderone's death, his drug cartel was crippled but not destroyed. His son, Orlando Calderone, took over the empire and began a campaign to avenge his father's death, by starting with the man he blamed for it, Tubbs.

Notes

• Calderone's first name in "Brother's Keeper" is said to be Orlando, but in later episodes it is changed to Esteban, which is now considered canon. The character's name is also listed as Esteban in the script for the series' pilot.
• There are further discrepancies in how the drug lord's surname is spelled throughout the series, with some instances spelling it Calderone (technically the Italian spelling of the name, and therefore unlikely to be adopted by a Central/South American drug dealer) and others spelling in Calderon (the anglicized version of the Spanish spelling, Calderón).
• His birthdate is shown to be 1940. He fathered Angelina (and her brother Orlando) in 1959, which would have made him 19 at the time; somewhat young, but completely plausible given his lifestyle as a drug lord (and the fact that he is presumably the son of a father in the same occupation).