Esteban Calderone

Esteban Calderone
Affiliation	Drug lord Head of the Calderone cartel
Born/Died	1940-1984
Status	Deceased, shot by James "Sonny" Crockett
Relatives	Orlando Calderone (son) Angelina Madeira (daughter) Ricardo Tubbs, Jr. (grandson)
Episode(s)	"Brother's Keeper" "Calderone's Return (Part II)"
Played By	Miguel Piñero

Esteban Calderone (1940-1984) was a powerful drug dealer and the leader of the Calderone cartel. Originally based in Miami, Calderone's operations stretched from New York to The Bahamas and beyond, and by 1984 he was considered one of the principal importers of cocaine into the United States. He was the target of a major Organized Crime Bureau investigation that eventually led to his arrest, but before he could stand trial he escaped custody and fled the country, presumably to South America.

Calderone later planned a return to Miami, hiring international hitman Ludovici Armstrong to assassinate many of his competitors ahead of his arrival, but was killed soon afterwards in The Bahamas by Detective James "Sonny" Crockett.

Biography

Early life

Not much is known about Calderone's early life. He was not well educated -- he never graduated past fourth grade in school. In 1959 he fathered a daughter, Angelina Madeira. He began his drug empire around 1966 (per the DEA file on him) and by 1984 was wanted by numerous law enforcement agencies, including the FBI, ATF, DEA, Metro-Dade and others. However, Calderone was able to escape prosecution by using his considerable wealth (amassed through decades of successful drug trafficking and said by himself to be "42 million dollars, tax free") to buy off anyone, including police officers, attorneys, judges or clerks, thus ensuring his empire remained untouched.

New York/Miami activities

By 1984, Calderone was running drugs into the United States through Miami to New York, where his activities caught the attention of NYPD Vice Detective Rafael Tubbs, who began working undercover to bring him down. He and his partner Tooney arranged a deal with Calderone, but unknown to them an informant had revealed to the drug lord of their true identities -- both men were shot dead during the botched deal. The incident was witnessed by Tubbs' brother Ricardo, who developed a personal vendetta against Calderone as a result, following the drug lord to Miami under false credentials with the intention of avenging his brother's death.

Tubbs linked up with Metro-Dade detective James "Sonny" Crockett, and together the two cops were able to meet Calderone through his lieutenant, Trini DeSoto, and arrange a deal. However, much like his brother before him, Tubbs was exposed by a Calderone informant, DEA agent Scottie Wheeler, and Calderone sent DeSoto to eliminate him; Tubbs was saved by Crockett, while DeSoto was killed. Determining the location of a Calderone shipment being brought into the country that night, Crockett and Tubbs confronted Calderone, who soon found himself staring down the barrels of a shotgun held by Tubbs. Despite his desire for vengeance, Tubbs refrained from killing him, and Calderone was taken into custody. However, within hours the drug lord had bribed a judge to secure his release, and he fled the country by seaplane as Crockett and Tubbs looked on in vain.

Calderone returns

Soon after leaving Miami, Calderone began planning his return to the city. To this end, he hired Argentinian hitman Ludovici Armstrong to eliminate his competition in the Miami area, chiefly former associates who had gone into business for themselves since his enforced exile. Also on Armstrong's list was the cop whom Calderone blamed for his having to vacate Miami -- Crockett. The drug lord dispatched one of his middlemen, Carlos Mendez, to act as the hitman's handler, while he himself remained safely out of the country. Armstrong initially met with much success, eliminating seven of the eight names on the list, but was ultimately killed by police before he could assassinate Crockett, while Mendez was arrested. Under intense interrogation, Mendez revealed that Calderone was due to meet with Armstrong in The Bahamas to settle the hitman's final payment.

Learning that Calderone had never actually seen Armstrong, Crockett assumed the hitman's identity and he and Tubbs travelled to St. Andrews Island in The Bahamas to apprehend the drug lord. While there, Tubbs met and began a relationship with Calderone's daughter, Angelina (leading to the conception of Calderone's grandson, Ricardo, Jr.). When Calderone heard of Crockett's supposed death through a phoney newspaper obituary and learned that "Armstrong" had arrived on the island, he dispatched Guillermo Pino to meet with the hitman and settle his fee. However, unknown to the two Vice cops, Calderone had actually discovered, through the island's corrupt chief of police Albury, that Armstrong was in fact Crockett working undercover -- as well as Guillermo, Calderone dispatched four shooters to kill Crockett and Tubbs, although they failed in their assignment.

Death and legacy

Unperturbed, Calderone sent more men after the Vice cops, and they eventually succeeded in capturing Crockett at a Junkanoo beach party, although Tubbs escaped. Calderone had Crockett brought to his palatial mansion on the island, where he intended to have him executed, but Tubbs (with Angelina's assistance) burst in at the last moment to save his partner. A shootout ensued, during which Crockett killed Calderone, emptying the entire magazine of a sub-machine gun into the drug lord's chest, his lifeless body tumbling into his pool.

Following Calderone's death, his drug cartel was crippled but not destroyed. His son, Orlando Calderone, assumed control of the empire and began a campaign to avenge his father's death, focusing his rage on the man he blamed for it -- Tubbs.

Notes

• Calderone's first name in "Brother's Keeper" is said to be Orlando, but by "The Afternoon Plane" it has changed to Esteban (his first name is not mentioned in either "Calderone's Return (Part I)" or "(Part II)"). Given that his son was later named Orlando, Esteban is considered canon. Interestingly, 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). When speaking about Calderone, most characters seem to assume "Calderone" as the correct spelling, pronouncing the name with a long "o" at the end, instead of a short "o", which an accented "ó" in the actual Spanish spelling of the name would indicate.
• 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).