"Legal" and "illegal" slave trade
As the early importing of enslaved Blacks into La Española continued during the second decade of Spanish colonization, the year 1506 marked the first recorded indication of what would become one of the characteristic features of Black slavery in the colony throughout the century: the smuggling of slaves into the island. There is also an order from that year, issued by the Spanish Crown, indicating a suspicion that already smuggling of non-Christianized (or bozales) slaves into La Española was taking place contrary to the Crown’s explicit prohibition against such activity. A punishment with a fine of 1,000 pesos was decreed for those breaking this law or, if no payment was made, of one hundred lashes instead.
The great majority of the cases of sixteenth-century Blacks of La Española for which we have a more or less detailed archival record are those who arrived in the colony through officially authorized and controlled travel, the equivalent to what we usually describe today as documented travelers. One of the earliest recorded licenses to carry Black slaves was issued in September of 1502.. But throughout the century, as a result of a drop in the numbers of Spanish ships going in and out of the island that could bring in needed imports and take out exports, a growing illegal or contraband importation of African Blacks took place into the island-colony until it became a rampant contraband practice that, towards the last quarter of the century, acquired widespread proportions. (Resorting to terminology already used for decades before that in Iberian maritime contacts and exchanges with the societies of the African western coast, smuggled goods of any type, as well as particular instances of smuggling, were called rescates because they were, most of the time the result of bartering --referred to precisely with the word rescate in earlier decades-- rather than currency-based purchases.) In 1555, for instance, the authorities of Santo Domingo seized on suspicion of smuggling a Portuguese vessel that showed up in La Española with a shipment of enslaved Black Africans, justifying its great detour westwards across the Atlantic to La Española by the need for important repairs to the ship in order for it to continue its trip to Portugal. (See Manuscript No. 044)
The colonial condition of La Española’s population, with a high level of dependency on imports from the metropolis for consumption, required abundant labor to produce the exports that would guarantee the purchasing of the needed imports, constantly demanded more slaves and, from its early beginnings and throughout the century, La Española’s colonists and children of colonists seem to have been always hungry for additional slaves, regardless of the legality of the venue for their acquisition.
For free Blacks traveling legally to La Española during the 16th century, as in the case of free individuals in general, the basic requirement, besides the payment of the ship’s fare, was buying a royal or governmental licencia or license to travel, which also entailed providing proof of one’s identity by presenting witnesses, and demonstrating that one did not belong to any of the ethnic or social categories forbidden by the Spanish Crown from traveling to the New World. For enslaved Blacks taken across the Atlantic by individual Spanish masters or owners in small numbers (say, between one and a dozen), the master had to pay the Crown a licencia or fee for each “piece” or “head” of slave transported plus the fare for each. We know of dozens and dozens of individual enslaved Blacks who were taken to La Española in this fashion in the 16th century. In the meantime, some politically connected or economically powerful individuals, Spanish or otherwise, including high-ranking bureaucrats of or associates to the Crown’s court, and big financiers or merchants, could enjoy the privilege of purchasing an asiento or permit to import into La Española and other places of the Indies hundreds of enslaved Blacks, either in one bulky shipment or in several installments over a certain number of years, to then sell them in the colonies for a profit.
The port of entry for Blacks arriving at La Española legally (that is, under an official licencia or asiento) during the sixteenth century was usually that of Santo Domingo City, the colonial capital by the Ozama River’s harbor. It was the main official port of the colony, in accordance with Spain’s imperial monopolistic maritime-commerce laws. In the case of enslaved Blacks arriving accompanied by their masters or their masters’ representatives or associates, the latter would be allowed to disembark the enslaved once they showed their licencias de esclavos issued in Spain. In the case of larger quantities of enslaved Blacks arriving either legally under an asiento or captured as suspected smuggled merchandize by the local Spanish authorities along the island’s coasts without a valid asiento or licencia document, the slaves would be taken from the ship into some holding quarters either at the Atarazanas or royal warehouse next to the port and inside the walled city or in any other building turned into an improvised warehouse. From there they would be released to their owners or traffickers or, if confiscated as smuggled cargo, auctioned off by the local authorities. (See Manuscript No. 053)
In May of 1509, in its instructions to newly appointed Governor of La Española Diego Colón one of the sons of Christopher Columbus, the Crown reiterated (see Manuscript No. 040) the earlier order given to Governor Ovando in 1501 to restrict the importing of “Black slaves or other slaves” to those born under Christian rule. The reiteration of the order seems an indication that the Crown either knew that the smuggling was taking place or that it was likely to happen.
As the native population increasingly died off due to disease and forced labor, the colonial administration and the crown began to condone the introduction of African bozales. Late in 1509 or early in 1510 King Ferdinand ordered Casa de Contratación to send 50 “slaves” to work in the mines the king had appropriated for himself in La Española. In a document of January 22nd of that year the monarch reiterated the order, instructing royal officials in Spain that the slaves should be “the largest and sturdiest that you may have” and to send them off as soon as possible. There are indications that 36 slaves were sent first. According to another source another 100 were sent in April of that year. These Blacks were bought in Lisbon thanks to private moneys raised by some of the Crown’s officials. The fact that they did not fit the profile of Blacks born or raised under Spanish control constituted a departure from that goal, the Crown leaving the religious requirement aside, at least in this occasion, in exchange for economic convenience. 
In the spring of 1511 the king, concerned about reports that many individuals who qualified for a license to “pass” to the new colonies being stopped from doing so by the officials of Casa de la Contratación of Seville, and understanding that this harmed the interests of the Crown, sent an additional set of instructions to the agency in which, among a number of items, he ordered its officials to make sure they allowed former Black or white slaves who could prove their freedom and appeared capable of working to proceed and go to the Indies if they wanted to do so.. In a letter of July 6, 1511 to royal treasurer Miguel de Pasamonte the king confirmed the presence of an undetermined number of Black slaves working in the mines of La Española side by side with natives. (See Manuscript No. 039) In another letter written in July, the king further implicitly confirmed their presence when he expressed regret for the unexplained death of a number of Black slaves, ordering the official in charge of overseeing the mines to apply himself so that “they are well treated” and “so that they do not perish due to lack of good care and may be healthy and able to serve and work in the mines.”  (See Manuscript No. 038) Finally in another communication to the Casa de la Contratación in October, we find the mention of a shipment of Black slaves that had been sent by the Crown approximately a year and a half earlier, possibly in the spring or summer of 1510. (See Manuscript No. 012)
Furthermore, it seems that by then (1511) a notion prevailed among the colonists that the work by an enslaved Black was much more productive than that of an indigenous man, and this contributed to an increase in the demand for Black slaves. Private individuals, among them high-level officials of the Crown or members of the aristocracy were increasingly taking with them or sending small numbers of Blacks to La Española under licenses issued by the Crown during the early 1510s (see Manuscript No. 014).
On September 26, 1513 a special exemption was granted by the Crown to the settlers of La Española so that each one of them could import from Castille a Christianized female slave for household service in the colony. The King explicitly recommended the importing of female slaves to La Española’s colonial treasurer Pasamonte so that ‘in marrying the males slaves there, the latter create less worries of uprising.’ (See Manuscript No. 022)
It has been pointed out that from approximately 1513 onwards divergent perceptions of the importation of slaves became evident in La Española between those in the colonial bureaucracy (such as treasurer Pasamonte) who were mostly concerned about the social order and were recommending a halt in the importation of slaves to reduce the likelihood of rebellions, and those settlers who were mostly concerned about their economic livelihood, considered the availability of enslaved labor fundamental, and were seemingly less concerned about having to eventually deal with the slaves’ resistance or insubordination.. But in 1514 we find the Crown continuing to authorize licenses for some individuals to import small numbers (say, between one and six) of slaves into La Española. And evidence exists showing that at the time, some colonial government officials, like the contador (another of the treasury officials) of the city of Santo Domingo Gil González Dávila were clearly in favor of importing enslaved Blacks, which he recommended as a basic step to deal with the gold mining crisis taking place at that time in the colony.
In January 1516 King Ferdinand died  and was replaced by a Regent, Cardinal Cisneros, appointed to govern until the heir to the Crown, the Young Charles (later proclaimed as Charles V of Spain and I of Germany) became of legal age to be king. Regents Cisneros ordered a stop to the importation of slaves into La Española and other territories, possibly as an attempt to prevent the smuggling of slaves before more efficient controls on the importing were in place. But this order was very short lived, and by the time Cisneros passed away in November of 1517 the trafficking of Blacks had reportedly resumed. The initial assumption was that bozales would pose less resistance to enslavement, but at least by 1528, as a new set of ordinances issued in this regard show, they were engaging in the same fleeing as the ladinos did.
On December 20, 1518, three Jerónimo (Hieronimyte) friars arrived in Hispaniola as a new designated trio of governors appointed earlier by Regent Cisneros. Among their missions was the task of regrouping the Taíno population around independent communities away from the control of the encomenderos, the Spanish settlers who until then had been provided with scores of natives as forced laborers by the colonial authorities. This generated a lot of discontent among the encomendero population. The other circumstance the friars faced was the constant fleeing of many among the white settlers’ population. As a way out from the negative impact of the gold production crisis and the emigration of whites away from the island, the Jerónimos proposed development of agriculture, especially in the form of cane-sugar production, and an increase in the importing of Black African enslaved labor force to work in it.
Once king Charles V acceded to the throne of the growing empire, he sent oidor-judge Rodrigo de Figueroa to La Española to oversee and further propel the cane-sugar business. Judge Figueroa was to facilitate capital and loosen colonial restrictions in order to heighten the production of sugar. At the time, this expansion necessarily meant the importing of more enslaved Black people.
 Carlos Esteban Deive, La esclavitud del negro en Santo Domingo (1492-1844), Vol. I, Santo Domingo: Museo del Hombre Dominicano, 1980, p. 25.
 Saco, 1938: I, 98. Cited in Deive, Vol. I, p. 25.
 The license to transport “as many Blacks as they may want” was issued on September 12, 1502 to two Crown officials, a Juan Sánchez, from the royal treasury, and Alonso Bravo, a personal guardian of the queen, according to Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p.22.
 Diego Colón had been appointed Governor on August 9, 1508. The Crown’s instructions to him were issued on May 3rd, 1509. On that same date, the king, in an order directed to outgoing governor Ovando, had reiterated his concern about and firm opposition to the acceptance in the Indies of non-Spaniards (“estrangeros”) without a royal license and non-Christians or their immediate descendants (“offspring of reconciled ones or grandchildren of burnt ones"), indicating or hinting that both restrictions had been violated under Ovando. The king mentions a Genoese businessman active in Santo Domingo, and orders that he be punished with confiscation of his goods; he also mentions non-Christians as if some were actually in the island when he banned both “those that were in the said island as well as those that were to arrive afterwards” (“los que alla en esa ysla estavan como para los que despues fueren”). See Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 28.
 Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 28-29. This interest on the King's part coincided with requests in the same direction from royal colonial officials in La Española, who, according to a communication from the monarch, had pointed out the need for the same number of slaves in the island, “to break the rocks where the gold is found because the Indians reportedly are very slim and of little strength.”
 The royal order issued on January 22, 1510 referred to a prior one sent “in days past” (“en días pasados”). Chacón y Calvo: VII, 217. Cited in Deive, p. 29.
 Saco: II, 104. Cited in Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 29.
 Ayala, I, 372. Cited in Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 29.
 This shipment may also have been in response to the colonists in Santo Domingo City who [that same year? See the source] had been addressing the Spanish Crown to request for the first time to be exempted from the payment of a tax when importing enslaved Blacks to the colony so that gold extraction could be expanded, implying, therefore, that an easing of the taxes would encourage an increase in the importing of slaves. Rodríguez Demorizi 1978a, 79. Cited in Deive, p. 30.
 The exact date of the instructions is May 18, 1511. Archivo General de Indias, INDIFERENTE, 418,L.3, fo. 1v.
 Archivo General de Indias, INDIFERENTE,418,L.3, fo. 84v.
 The letter was dated in Seville, July 21, 1511. The text of the Crown’s order in its Spanish original, referring to the slaves, says: “trabajad como sean bien tratados asy de mantenimientos como de camas para que por falta de buen Recabdo no Se mueran y que esten sanos y buenos para servir y trabajar en las minas”. The original may be read in PARES, Portal de Archivos Españoles, Archivo General de Indias, INDIFERENTE,418,L.3, fo.89r.
 Archivo General de Indias, INDIFERENTE,418,L.3, fo. 181v.
 Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 31.
 The exact date cited for this letter is September 26, 1513. The original Spanish text says: “provease esclavas que, casándose con los esclavos que hay den estos menos sospechas de alzamiento" ("female slaves must be provided so that, marrying the male slaves that are there, these generate less suspision of uprising") Larrazábal, 1975, 16. Cited in Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 32. This statement may show, as Deive says, the ultimate intentions of the Crown with this introduction of female slaves. (Deive, p. 33).
 Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 33-34.
 Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 31-32.
 Carlos Esteban Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 34.
 The exact date of king Ferdinand’s passing was January 23, 1516. CODOIN I, 332-47. Cited in Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 34.
 Cisneros’ death occurred on November 18, 1517. Deive indicates this was the time of the first importing of bozales slaves, but as it has been shown before, non-Christianized slaves had been shipped to the Indies since at least 1504.
 Malagón, p. 128. Cited in Deive, La esclavitud del negro en Santo Domingo, Vol. I, p. 34-35.
 Carlos Esteban Deive, La Esclavitud del Negro en Santo Domingo, Vol. I, p. 36. The friars-governors were appointed by Regent Cisneros roughly a year before, on December 18, 1517.