While Rupesvara was knowledgeable in the Vedic literatures, his brother became expert in weaponry and politics. When their father died, the kingdom was divided between the two sons. However, Harihara took Rupesvara's land by force and forced the family to migrate to Paurastyadesa. Padmanabha relocated his family to Nabahatta (Naihati) on the banks of the Ganges River. Padmanabha had eighteen daughters and five sons, the youngest son being named Mukunda.
When there was religious upheaval, Mukunda's son, Kumaradeva, moved to Jessore. His sons were Santosha (Rupa), Amara (Sanatana) and Srivallabha (Anupama). On the demise of Kumaradeva, the three sons moved to Sakurma, near to the capital of Gaudadesa (Bengal) where they continued their studies.
The three brothers studied the Nyaya-sastras (treatise on justice) from the famous logician Sarvabhauma Bhattacarya and his brother Madhusudana Vidyavacaspati. They also studied Sanskrit, Arabic and Persian.
Due to their noble characters and academic proficiency, Rupa and his elder brother Sanatana were later forced into government service by the sultan of Bengal, Alauddin Hussein Shah (1493-1519 CE) which led to their excommunication from Hindu society by the orthodox caste brahmanas of Gauda. Rupa became the Sultan's chief secretary (dabir khas), while Sanatana became the state revenue minister (sakara mallika).
First meeting with Chaitanya Mahaprabhu
Rupa and his brothers made their residence at the state capital of Ramakeli and it was here, in 1514 CE, that they met Chaitanya Mahaprabhu for the first time. The meeting changed their lives and they decided to leave the service of the Sultan and take up a life of renunciation in the association of Chaitanya and his followers. Rupa loaded all his wealth onto two boats and left with his brother Anupama[disambiguation needed] for their ancestral home at Fatiabad in Jessore, where they distributed it. They then sent two messengers to Puri, now in Odisha to get news of Chaitanya Mahaprabhu's plans. The messengers returned with the news that Chaitanya had already left Puri for Vrindavana. Rupa and Anupama immediately decided to go and they wrote a letter to Sanatana telling him of their plans and asking him to meet them in Vrindavana. They also told him that they had left 10,000 gold coins in case he was in need of financial help. Later, when Sanatana was thrown into prison by the Sultan for disobedience, he used this money to bribe the jailer and escaped to Varanasi to meet with Chaitanya Mahaprabhu.
Second meeting with Chaitanya Mahaprabhu
After visiting Vrindavana, Chaitanya stopped at the holy city of Prayaga (modern day Allahabad in Uttar Pradesh). It was here that Rupa and Anupama met him for the second time. At the Dasasvamedha Ghat (a famous bathing area on the banks of the River Ganges), Chaitanya imparted instructions to Rupa Goswami and explained all the intricacies of the doctrine of Gaudiya Vaishnavism. Rupa Goswami was specifically commanded by Chaitanya Mahaprabhu to carry out two tasks: to re-locate and preserve the lost holy places of Vrindavana, and to write and preach Gaudiya Vaisnava theology. He then sent Rupa Goswami to Vrindavana to carry out these orders.
Later, on the order of Chaitanya Mahaprabhu, Rupa Goswami came to Puri and resided there for ten months. During the time of the annual Rath Yatra festival in Puri, Rupa Goswami composed one mystical verse that Chaitanya Mahaprabhu requested him to read to his most intimate associates. Upon hearing this verse, all the assembled Vaishnavas praised Rupa Goswami for his outstanding composition that was filled with deep devotion to Krishna. Due to this, it was proclaimed that Rupa Goswami was the very embodiment of Chaitanya' Mahaprabhu's esoteric teachings of rasa (divine mellows). Because of this, Rupa Goswami is considered by Vaishnavas to be the foremost follower of Chaitanya Mahaprabhu and those that strictly follow in his preceptoral line are known as Rupanugas (followers of Rupa).
Rupa and Sanatana remained in Vrindavana for the remainder of their lives. Their mood of renunciation and devotion was exemplary. Rupa uncovered various holy places associated with the pastimes of Krishna and rediscovered the famous deity of Govindadeva, which was originally installed and worshipped by Krishna's great-grandson, Maharaja Vajranabha. Rupa and Sanatana were intimately connected with other Vaishnava saints in Vrindavana such as Lokanatha Goswami, Bhugarbha Goswami, Gopala Bhatta Goswami, Raghunatha Bhatta Goswami and Raghunatha Dasa Goswami.
Shortly after, they were also joined by their nephew Jiva Goswami who was given initiation by Rupa and personally trained by him in the philosophy of Gaudiya Vaishnavism.
Rupa Goswami departed from this world in 1564 CE and his samadhi (tomb) is located in the courtyard of the Radha-Damodara temple in Vrindavana.
In Gaudiya Vaishnava theology, Rupa Goswami is considered to be the incarnation of Rupa Manjari, the foremost junior cowherd damsel who eternally serves Radha-Krishna under the guidance of Lalita (gopi).
Even though there are so many great acaryas, Srila Rupa Goswami has been attributed with the honor of being that person who has established the mano-‘bhistam, the innermost heart’s desire, of Sri Krsna in the form of Caitanya Mahaprabhu. When Sriman Mahaprabhu came to the village of Ramakeli-grama, He met with Srila Rupa Goswami and Srila Sanatana Goswami and told them, "You should leave your homes and be with Me."
After a short time they left their homes, and Sri Caitanya Mahaprabhu came from Vrndavana and met with Srila Rupa Goswami at Prayag, the confluence of the rivers Yamuna and Ganges. Sri Caitanya Mahaprabhu told him: