Śrī Śyāmānanda Prabhu was a servant of a servant of Subala in Kṛṣṇa-līlā. He was the disciple of Hṛdayānanda or Hṛdaya Caitanya, a disciple of Gaurī Dāsa Paṇḍita, who is Subala in Kṛṣṇa-līlā.

yaṁ lokā bhuvi kīrtayanti hṛdayānandasya śiṣyaṁ priyaṁ
sakhye śrī-subalya yaṁ bhagavataḥ preṣṭhānuśiṣyaṁ tathā
sa śrīmān rasikendra-mastaka-maṇiścitte mamāharniśaṁ
śrī-rādhāpriya-narma-marmasu ruciṁ sampādayan bhāsatām

Śrī Śyāmānanda was known in this world as Hṛdayānanda’s dear disciple. Due to his being a follower of Subala sakhā, he became the grand-disciple of the Lord’s dear associate. May he, the crest-jewel of the connoisseurs of divine love, appear day and night in my mind, bringing me a fondness for the service of Śrī Śrī Rādhā-Mādhava’s confidential joyous pastimes. (Śyāmānanda-śataka)

Śyāmānanda Prabhu was born on the full moon day of Chaitra in 1456 of the Śaka era (1535 AD) in the town of Dharenda Bahadurpur, which is near the Kharagpur railway station in Midnapore. His father was Śrī Kṛṣṇa Maṇḍala and his mother, Durikā. Kṛṣṇa Maṇḍala’s hometown was Dandeshwar, which lies on the banks of the Subarnarekha River. The following statement is found in the Gauḍīya Vaiṣṇava Abhidhāna: “Śrī Kṛṣṇa Maṇḍala used to live in a place called Ambua, near Dandeshwar. He formerly lived in Gauḍa (the part of Bengal which lies on the banks of the Bhagirathi River) and only later moved to Dandeshwar, just across the present-day border in Odisha. Śyāmānanda Prabhu’s Sripats in the towns of Dharenda, Bahadurpur, Rayni or Rohini, Gopiballabhpur and Nrisinghapur are very dear to his disciples.”

Śyāmānanda Prabhu was born in the Sadgopa sub caste. Of course, a Vaiṣṇava is beyond the material qualities and may take birth in a family of any race or caste. If anyone thinks badly of Vaiṣṇavas or judges them based on their race or caste are destined for hell.

arcye viṣṇau śīladhīḥ guruṣu naramatir vaiṣṇave jāti-buddhir
viṣṇor vā vaiṣṇavānāṁ kali-mala-mathane pāda-tīrthe ’mbu buddhiḥ
śrī viṣṇor nāmni mantre sakala-kaluṣahe śabda-sāmānya-buddhir
viṣṇau sarveśvareśe tad-itara-samadhīr yasya vā nārakī saḥ

Anyone who considers the deity to be nothing, but stone, the guru to be an ordinary human being, or the Vaiṣṇava to be a member of a particular caste or race, who takes the holy water which has washed Viṣṇu or the Vaiṣnava’s feet and can destroy all the sins of the age of Kali, to be ordinary water, who thinks that the Name or mantra of Viṣnu, which destroys all evils, is the same as any other sound, or who takes Viṣṇu to be equal to anything other than Him, has to suffer hellish life. (Padma-purāṇa)

One who takes birth in a low-class family is not disqualified from performing devotional service, nor is one who is born into a pure, high-class brahminical family automatically qualified for such service. Whoever engages in the worship of the Lord is a great person; one who does not worship is rejected. There is no consideration of caste or creed in Kṛṣṇa-bhajana. (Caitanya Caritāmṛta 3.4.66-7)

na me bhaktaś caturvedī
mad-bhaktaḥ śvapacaḥ priyaḥ
tasmai deyaṁ tato grāhyaṁ
sa ca pūjyo yathā hy aham

Simply being a knower of the four Vedas does not make someone My devotee. An outcast, who is My devotee, is dear to Me. One should exchange gifts and food, etc., with such a devotee as he is verily as worshipable as I am. (Itihāsa-samuccaya, quoted in Hari-bhakti-vilāsa 10.127)

Śyāmānanda’s parents had lost several children in childbirth and they vowed to surrender their next child to Viṣṇu if it survived. Having suffered so much grief in the loss of their previous children, they first named Śyāmānanda as Duḥkhī, or “unhappy”, to ward off further distress.

Śyāmānanda’s parents, Durikā and Śrī Kṛṣṇa Maṇḍala, made their home in Dandeshwar. His father was the best of the Sadgopa caste, of impeccable character. Kṛṣṇa was everything to him and Kṛṣṇa’s devotees very dear. We cannot describe the virtues of his parents for fear of increasing the volume of this book. They had previously lived in Dharenda-Bahadurpur and people say that Śyāmānanda was born there. Though his brothers and sisters had all died as children, nothing could stop him. Even so, his parents brought him up in sadness and they called him ‘Duḥkhī’. (Bhakti-ratnākara 1.351-5, 359)

Duḥkhī’s parents performed the appropriate rituals such as the first eating of solid food, and the cutting of hair, when their time came. As he grew older, he studied Sanskrit grammar, etc. His parents were overjoyed to see his talents and his religious proclivity. He listened attentively to devotees, when they spoke of Gaurāṅga and Nityānanda Prabhu’s glories and would repeat them to others constantly. Whenever, he listened to the activities of Gaura-Nitāi or Rādhā and Kṛṣṇa, tears would flow in torrents from his eyes.

Duḥkhī served his parents devotedly and they told him to get initiated, so that he could fully commit himself to the service of the Lord. Duḥkhī agreed and told them that he wished to take dīkṣā from Hṛdaya Caitanya in Ambika Kalna. Going there would also give him the chance to see the Ganges and to bathe in it. His parents happily permitted him to go.

When Duḥkhī arrived in Ambika Kalna, he threw himself at the feet of Hṛdaya Caitanya, who upon becoming acquainted with him, happily gave him kṛṣṇa-mantra. He gave Duḥkhī the Vaiṣṇava name “Kṛṣṇadāsa” and so he was known from then on as ‘Duḥkhī Kṛṣṇadāsa’. Hṛdaya Caitanya ordered him to go to Vṛndāvana and take up a life of intense bhajana. Though, Duḥkhī Kṛṣṇadāsa did not like being separated from his gurudeva, following his orders, he set off for Vraja, first visiting Navadvīpa and other places in Gauḍa-maṇḍala, where he sought the blessings of the Vaiṣṇavas. After spending much time on pilgrimage, he finally arrived in Vṛndāvana where he became completely absorbed in the worship of Śrī Rādhā-Śyāmasundara.

In Vṛndāvana, Duḥkhī Kṛṣṇadāsa studied the Vaiṣṇava scriptures under Śrī Jīva Gosvāmī, who was the leading scholar of the sampradaya. When Hṛday Caitanya heard of the enthusiasm with which Duḥkhī Kṛṣṇadāsa was leading his devotional life in Vraja, he wrote a letter to Jīva Gosvāmī, in which he said that Jīva Gosvāmī should accept Duḥkhī Kṛṣṇadāsa as his disciple. Just as he gave titles to his other prominent students (Ācārya title to Śrīnivāsa and Ṭhākura to Narottama), Jīva Gosvāmī gave the name ‘Śyāmānanda’ to Duḥkhī Kṛṣṇadāsa. The reasoning behind this name was that he brought great joy to Śrī Rādhā-Śyāmasundara.

He brought great joy to Śyāmasundara and hence he was given the new name ‘Śyāmānanda’ in Vṛndāvana. Seeing his sincere endeavour in devotion, Śrī Jīva Gosvāmī taught him devotional scriptures. (Bhakti-ratnākara 1.401-2)

Jīva Gosvāmī sent Śrīnivāsa Ācārya, Narottama Dāsa Ṭhākura and Śyāmānanda Prabhu back to Bengal with the Vaiṣṇava scriptures written by the Gosvāmīs in 1504 of the Śaka era (1582-3 AD). The idea was to spread the teachings found in these books throughout Bengal and Odisha. We have already related the events that took place when Bīrahāmbīra stole these books. Narottama Ṭhākura went to northern Bengal and Śyāmānanda Prabhu went to Odisha. The Midnapore district was previously under the rule of the Odishan king.