At this moment the Admiral was again in the Gulf of Paria, close to the Orinoco river mouth, after discovering mainland, in other words, the Great Continent. The third voyage was short; by August 1498, Christopher was arriving to the shores of the Ozama river, but the three ships that had been sent from the Canaries were delayed and by chance landed in the Jaragua coast where Roldan and his people appropriated the provisions and convinced the newly arrived to join their group. The fleet's captains, however, refused to disobey the Admiral and promptly sailed for Santo Domingo arriving only a few days after Columbus.
During his first days in the new city the Viceroy confers with his brothers Bartholomew and Diego and receives the message that his old squire and mayor was headed to Santo Domingo to meet with him. In these moments, discontent of the Spanish residents it was absolute – the tribute system had not produced the expected quantities of gold , very few natives had converted to Christianity, the majority of European men had died of diseases, and many, including the newly arrived were infected with syphilis or "French sickness".
With the situation so out of control and very few men to face the rebels, the Admiral decides to pardon them and allow anyone who wants to leave to return in the next voyage to Spain he was already preparing.
Trying to counteract the information that would be arriving at the court about his failures in government, the Viceroy tries to rapidly generate gains with another new tribute of Palo de Brazil (Brazilwood) from which he expected to amass 4,000 quintals as well as the sale of 3,000 Indian slaves captured in the recent island rebellions. He delays the departure of the fleet until October hoping that Roldan and some of his men would return to Spain; none of the solutions resulted the way he wanted and ended up sending five ships loaded with a smaller quantity of wood, 800 slaves, cotton, samples of the pearls he found in Gulf of Paria, and a limited amount of gold. He sent as well long letters to the monarchs announcing the discovery of mainland, denouncing the acts of Roldan and asking for all types of help and more religious people to convert the Indians and placate the Christians.