Brest-Litovsk (Brisk, Heb.) capital of Brest oblast, Belorus. In the medieval grand duchy of Lithuania, from the 14th to the 17th centuries, it was the main center of Lithuanian Jewry. Its situation on the River Bug, at the junction of commercial routes and near the borders of Lithuania and Poland, made Brest-Litovsk an important communications and commercial center. The first Jews settled there under the grand duke Kiejstut (1341–82). His son Vitold granted them a generous charter in 1388, which was later extended to all the Jews in the duchy. Jewish merchants from Brest-Litovsk are mentioned in 1423–33 in the muncipal records of Danzig (Gdansk) where they bought textiles, furs, and other goods. The community increased toward the end of the 15th century, and became one of the largest in Lithuania. It also became the most important organizationally as contacts with Poland steadily expanded. The Jews of Brest-Litovsk engaged in commerce, crafts, and agriculture. Some conducted extensive financial operations, farming the customs dues, taxes, and other government imposts. They also farmed and owned estates. Their business connections extended throughout and beyond the duchy. In 1495 all Jews who refused to accept Christianity were expelled from Lithuania. Only one convert, of the Jozefowicz family, remained behind. The Jews were permitted to return in 1503, and the community regained its former eminence. Records of 1566 show that there were 156 Jewish-owned houses in the town out of a total of 746. Two years later, after the great fire there, the Jews were exempted by King Sigismund Augustus from paying tax for nine years, provided that they thenceforth built their homes of stone only. In Brest-Litovsk the Jews could continue to engage in agriculture, and 16% of the real estate was Jewish-owned. The influential Saul Wahl of Padua, who lived in Brest-Litovsk, established a synagogue and yeshivah in the town.

The satisfactory relationship between the Jews and the townspeople in the 16th century subsequently deteriorated. In 1636 Christian students made a savage raid on the Jews. The Lithuanian Council defined it as a "calamity" and treated it as a matter of concern to Lithuanian Jewry as a whole, to be dealt with at its expense. Jewish stores were looted and burned in 1637 by the townspeople, but the Polish authorities compelled the municipality to restore the stolen merchandise to its Jewish owners and punish the rioters. A mixed Jewish-Christian watch was instituted to guard the stores. Despite the increasing anti-Jewish feelings fostered by the clergy, kings Sigismund III and Ladislas IV ratified the Jewish charters. During the Chmielnicki uprising of 1648–49 many Jews who had the means escaped from Brest-Litovsk to Great Poland and Danzig; hundreds of those who remained were massacred (according to one source, 2,000). Shortly afterward, Jews resettled in Brest-Litovsk and were granted a charter of protection in 1655. The wars with Russia, Sweden, and Turkey caused much hardship among the Jews, and many were massacred by the Russian army in 1660. In 1661, in order to relieve their economic distress, the king exempted the Jews from the obligation to billet troops and all other taxes for four years; Jewish debtors were granted a three-year moratorium. In 1669 King Michael Wisniowiecki confirmed the privileges granted in former charters, and permitted the Jews to retain the land and buildings they had owned before the wars, including synagogues, courthouses, public baths, cemeteries, and stores. Jews were permitted to engage in every sphere of commerce and crafts, and required to pay only the same taxes as Christians. The municipality and non-Jewish citizens were ordered to cooperate in suppressing anti-Jewish agitation. The privileges were ratified in 1676 and in 1720. 22 Jewish merchants were recorded in the city in 1662, ten of whom were innkeepers who paid a special tax. By 1676, there were 525 Jews (excluding children under 11) living in Brest-Litovsk. The number grew during the 18th century. The 1766 census recorded 3,353 Jews in the town and its environs. There were fresh disturbances between the Jews and the non-Jewish citizens, in particular in 1792.

Brest-Litovsk was a stronghold of the Mitnaggedim in opposition to Hasidism. Some of the early disputations between the leaders of the two trends took place there. After its incorporation into Russia in 1793 the economic importance of Brest-Litovsk diminished. Many historic edifices of the Jewish quarter, including the old synagogue and cemetery, were demolished to give way to the building of a fortress in 1832. The economic position again improved after the completion of the Dnieper-Bug Canal in 1841, and the Jewish community, which handled most of the commerce and industry in the city, began to grow appreciably. A tobacco factory and two large mills were established by Jews in 1845. A hospital was erected in 1838, a new synagogue during 1851–61, and a home for widows in 1866.