Along with the first few rulers of the Iliyas Shahi dynasty, and Rukn-ud-din Barbak Shah, Hussain Shah is probably the most well known ruler of medieval bengal. His father, Sayyid Ashraf al-Hussaini, is said to have come to cÃpur = cÃpAD.A from Tarmuz in Turkisthan along with him and his younger brother Yusuf. On the other hand, there are stories of him being an Arab merchant, or having been born in devanagar in bodA in raMpur of a hindu mother, and he is said to have been dark skinned. He married the daughter of his teacher, the Qazi of cÃpur. Stories prevail about his working as a cowherd for a brahmin there, to whom he sold cÃpAD.A for 1 anna when he became the sultan; and whom he, because of his wife, later forced to eat beef. Similarly, he is said to have worked under Subuddhi Ray, the local governor of gauD.a, who had whipped him; after becoming the sultan he is supposed to have raised Subuddhi to high posts, but later, on his wife's request, made him drink from a muslim pot.
In 1495, Hussein Shah Sharqi, the displaced ruler of Jaunpur, fled to Bengal after an unsuccesful bid against Sikandar Shah Lodi of the Delhi Sultanate. The resulting conflict between Bengal and Delhi was avoided by a treaty that forbade either side from supporting the other's enemies. However, he did conquer parts of bihar including trihut, and when Sikander Shah Lodhi sent an army against his own governor Hussein Khan Formuli of sAraNa in Bihar, Hussein supported the latter in violation of his treaty. After 1517, when Sikander died, he openly declared his enemity against the sultanate representatives in Bihar.
Hussein Shah fought a long battle with Orissa starting in 1493 when puruSottamadeva was ruling there, till about 1515 when it was under pratAparudra who came to the throne in 1497. There was no clear winner in this battle,but at various times he captured all the way to the capital Cuttack, and destroyed many idols in the jagannAtha temple in puri; only the jagannAtha idol itself was whisked away to caD.Aiguha mountains in the cilkA and got saved, and at others he was defeated and had to retreat into the mAndAraNa fort.
In 1498–99, Hussein Shah conquered kAmatApur = Kochbehar and kAmarUpa = western Assam, according to legend, by treacherous means. Similar legends say that koca king vishvasiMha regained ATgÃo, and the muslims were pushed out of kAmatApur by 1513. Also according to various sources, Hussein = khunaphaM = khuphaM Shah also tried to capture Assam = Ahom (eastern and southern Assam) under suhuGga muGga, and though he may have had temporary success establishing his son dulAla gAji as the king, the assamese army under general baraputra gohAina defeated the Bengali army, which was under ‘big minister’ and bit mAlika, killed dulAla, and reoccupied Assam.
By 1513, Hussein had also occupied parts of Tripura, and made a thaoAs khAn its sar-e-laskar. According to tradition, by 1513, when the tripura king dhanyamANikya had occupied caTTagrAma, Hussain Shah sent his general gaurAi mallika, who occupied large parts of tripurA. Next year, under generals rAikachAga and rAikachama, tripura reconquered caTTagrAma, but Hussein's general haitan khà again reconquered it and large parts of tripurA.
The arakan king also occupied caTTagrAma, but lost to Hussein's army under the generalship of his son nasarat shah, and arakan accepted the overlordship of Bengal.
Hussein was known for the law and order which he established in Bengal. He constructed dams, mosques, inns, and madrasas; the choTi sonA masajida and gumati phaTaka of gauD.a date back to his times. But his continuous wars led to pitiful plight of his subjects in the famine of 1509.
Even though he was a staunch muslim, and did not do much to stop the oppression of hindus, many hindus like vallabha, shrIkAnta, his sister's husband, ciraJjIva sena, father of govindaAsa kavirAja, kavishekhara, dAmodara, yashorAja khAn, vaidya mukunda, and chatrI keshava khAn, were placed by Hussein in high posts. His officers, parAgala khAn, governor of caTTagrAma, and his son chuTi khAn = nasrat khAn, had the mahAbhArata translated into Bengali by parameshvara and shrIkara nandI respectively. sagIra mAlika = sAkara mallika = sanAtana, vallabha's brother and his yonger brother rUpa, both famous because of association with caitanya, were Hussein's chief secretaries.
Shri Chaitanya lived during his reign, and Bengali art and culture flourished. It is, however, not clear how much he explicitly supported such activity.
Up to history of Hussein Shahi dynasty