The history of the Jews in North Macedonia stretches back two thousand years, beginning during Roman antiquity, when Jews first arrived in the region. Today, following the Holocaust and emigration, especially to Israel, 66 Jews remain in North Macedonia, mostly in the capital, Skopje and a few in Štip and Bitola.

Ancient Roman times The first Jews arrived in the area now known as North Macedonia during Roman times, when Jews fled persecution in other Roman territories, with some settling in the Roman territory of Macedonia. The presence of Jews in North Macedonia is attested by Agrippa's letter to Caligula.Philo, "Legatio ad Caium," § 36 [ed. Mangey, ii. 587]

At Stobi, in 165 AD, Tiberius Polycharmus, who is designated "father of the synagogue", converted his villa into a synagogue containing a prayer hall, a triclinium (dining hall) and a portico, reserving the upper story of the complex for his residence and that of his successors. The information comes from a very impressive and informative inscription, arguably the most important one found to date in a Diaspora synagogue.

The remnants of a Jewish synagogue excavated in Stobi (North Macedonia) date back to that period and the conclusion that a developed Jewish Community existed in that locality those days is based on these findings.

Medieval times The Jewish community persisted in North Macedonia (as well as in the rest of the Macedonian region) after Roman rule. The medieval Jewish population of North Macedonia consisted until the 14th-15th century primarily of Romaniote Jews.Bonfil, R. et al. Jews in Byzantium: Dialectics of Minority and Majority Cultures, Robert Bonfil, 2011 The First Crusade devastated the Jewish population in Pelagonia and Skopje. However, the Jews in North Macedonia continued to have prominent members of their communities. For instance, Leo II Mung, the Philosopher, converted to Christianity and succeeded Theophylactus of Ohrid as the archbishop of Ohrid from 1108 to 1120. A leading Jewish scholar, Judah Leon ben Moses Mosconi, born in Ohrid in 1328, wrote commentaries stating that incorrect interpretations of scripture often resulted from neglect of grammar. The Late Medieval Balkans: A Critical Survey from the Late Twelfth Century p. 450 He later became the physician of the king of Majorca, where he assembled a vast library that was used by scholars for centuries to come. Daily life of the Jews in the Middle Ages p. 143 The first known synagogue in Skopje, Beth Aharon, was built in 1366. Les Juifs d'Espagne: histoire d'une diaspora, 1492–1992 p. 274

Ottoman Rule and Sephardic migrations

The area's Jewish community remained small well into Ottoman times, with the next major influx of Jews to the area coming with the Spanish and Portuguese Inquisitions, and Sultan Bayezid II of the Ottoman Empire welcomed Jews who were able to reach his territories. They were granted significant autonomy, with various rights including the right to buy real estate, to build synagogues and to conduct trade throughout the Ottoman Empire.A. Assa, p.36. Wealthy merchant cities in the present-day North Macedonia such as Skopje, Monastir (present-day Bitola) and Štip attracted many Jews. Jews in this area prospered in the fields of trade, banking, medicine, and law, with some even reaching positions of power. The Jewish cemetery in Bitola was established in 1497, soon after the first Sephardic Jews moved to the area. The cemetery is the oldest Jewish cemetery in North Macedonia, if not in the Balkans overall.

Relations between the Jews and the local non-Jewish population were generally good. Confirmation of good conditions for Jews in North Macedonia (and the broader Macedonian region) and Ottoman Europe in general comes from a 15th-century letter from the Macedonian Jew, Isaac Jarfati, sent to German and Hungarian Jews advising them of the favorable conditions in the Ottoman Empire, and encouraging them to immigrate to the Balkans.Assa, p.40. An Italian traveler wrote in 1560 that in Skopje Jews exceeded other populations in number. Encyclopedia of the Jewish diaspora: origins, experiences, and culture, Volume 1, p. 980 In the 17th century, there were 3,000 Jews and two synagogues in Skopje, Beit Aron and Beit Yaacov. The Expulsion of the Jews: Five Hundred Years of Exodus By Yale Strom p. 17 In 1680, Nathan of Gaza died and was buried in Skopje. Sephardi and Middle Eastern Jewries: history and culture in the modern era By Harvey E. Goldberg, Jewish Theological Seminary of America p. 75 His burial place was a pilgrimage site after his death, but it would not become a permanent pilgrimage site, since it was destroyed in World War II. Honored by the Glory of Islam: Conversion and Conquest in Ottoman Europe By Marc David Baer p. 300

At one point, Bitola had nine synagogues, Skopje three and Štip had two.

Several notable Jewish philosophers are born or lived for a time in North Macedonia, including Samuel de Medina, Josef ben Lev, Shlomo Koen, Kirco Blazevski, Jaakov tam David Yahia, Ishaak ben Samuel Adrabi, Aharon ben Josef Sason, and Salamon.[ books.google.com/books?id=NoPZu79hqaEC&pg=PA980] Encyclopedia of the Jewish diaspora: origins, experiences, and culture, Volume 1, p. 980

Piccolomini's burning down of Skopje in 1689 and a massive fire in Bitola in 1863 significantly diminished the Jewish population in North Macedonia in the two largest Jewish centers. In 1689, the Jewish population of Skopje was 3,000 of the total 60,000 population.

The Jewish community was almost entirely Sephardic, and most spoke Ladino at home. 1895 the Alliance Israelite Universelle established a school in Bitola. More than 30% of Macedonian Jews spoke French at this time.

Jews also took part in the liberation movement against Ottoman rule. A great number of Macedonian Jews participated in the Ilinden-Preobrazhenie Uprising. One of the most notable participants was Rafael Moshe Kamhi who led one of the rebel groups. It was he who took part in the early activities of the movement under the nickname Skanderbeg (Skender-beg). He headed a unit in Debar during the uprising of 1903. Mentes Kolomonos, Santo Aroesti, the Muson brothers and Avram Nisan are other known participants in the uprising who collected weapons and provided rebels with money.,

Jews from modern-day North Macedonia got their citizen rights after the region became a part of Kingdom of Serbia.

Distribution Prior to World War II, the Jewish community of Vardar Macedonia (the area roughly corresponding to the borders of the present-day republic) was centered on Bitola (approximately 8,000 Jews), Skopje (approximately 3,000 Jews) and Štip (approximately 500 Jews). The Jewish communities during World War I in smaller areas, like Dojran and Strumica, that were close to the front line, were significantly affected by the fighting and fled the area. The partition of the region also adversely impacted the Jews in the smaller centers since it deprived them of free flow for most of their merchant activities to the largest Jewish trading center in the Balkans, Thessaloniki.

World War II and the Holocaust

In March 1941, Bulgaria became an ally of the Axis Powers and in April 1941 the Bulgarian army entered Vardar Macedonia, in an effort to recover the region, which it saw as a natural part of its own national homeland.

Bulgarian authorities had already adopted an antisemitic law called "Law for Protection of the Nation"

in January 1941.Bulgaria, Holocaust Encyclopedia According to the U.S. Holocaust Museum, "on October 4, 1941, the Bulgarians enforced an extraordinary measure that prohibited the Jews of Macedonia from engaging in any type of industry or commerce." Over the course of 1942, they enacted increasingly harsh measures against the Jews under their control in Vardar Macedonia, as well as in occupied northern Greece. Some of the harsh demands by the Bulgarian government were that all "Jewish households hand over 20 percent of the value of all assets." The harsh measures culminated in 1943 with the deportation, upon orders from Germany, of "Macedonian Jews" and Greek Jewry to the Bulgarian border on the river Danube. From there they were transported with German boats and trains to the German death camp Treblinka in occupied Poland.Shlomo Alboher, The Jews of Monastir Macedonia - The Life and Times of the Departed Jewish Community of Bitola Vera Rich, Bulgaria: Shadows of the holocaust, The Lancet, Vol. 337, Issue 8750, Page 1152, 11 May 1991. Jews from Skopje, Stip, and Bitola, approximately a total of 7,215, were kept in "crowded, filthy conditions in four warehouses at Monopol" for 11 days before being put on trains to Treblinka.Interview with Shela Altaraz, Holocaust Survivor from Štip, Yad Vashem website

Nazi Germany even requested that Bulgaria finance the deportations. On February 22, 1943, an agreement was signed between Theodor Dannecker, the special Nazi envoy sent to facilitate the deportations, and the Bulgarian Commissar for Jewish Affairs, Alexander Belev to deport 20,000 Jews (12,000 from Vardar Macedonia and Thrace and 8,000 from Bulgaria proper). This is the only agreement that a country ever signed with Nazi Germany for deportation of Jews. Bulgaria had to pay all transportation costs and promise never to claim those Jews as citizens.The Miraculous Rescue of the Bulgarian Jews during the Holocaust (1939 – 1945) (The Bulgarian Miracle) (Part 1) by Dr. Marcel Israel.

Many Jews joined the partisans fighting the Nazis in Yugoslavia. In Vardar Macedonia, Estreya Haim Ovadya, a Jewish woman from Bitola, was among the first women to join the partisan movement in 1941. The day before the deportations, the Central Committee of the Communist Party of Macedonia gave the Jewish community advance warning of the deportation. Shelters were organized, as well as connections to the partisan units, but unfortunately, few Jews believed that a program for their destruction was underway and chose to stay together in the ghettos instead. Biographical dictionary of women's movements and feminisms in Central, Eastern, and South Eastern Europe: 19th and 20th centuries edited by Francisca de Haan, Krasimira Daskalova, Anna Loutfi p. 382 In contrast with the old Bulgarian territories, where widespread protests against the deportations took place, including petitions to the Sofia government, in Vardar Macedonia such organized movements were lacking. Beyond Hitler's Grasp: The Heroic Rescue of Bulgaria's Jews, Michael Bar-Zohar In the early morning of Thursday, March 11, 1943, Bulgarian police and army rounded up the entire Jewish population of Skopje, Bitola and Štip.Holocaust Encyclopedia -The Holocaust in Macedonia: Deportation of Monastir Jewry, The population was sent to a temporary detention center at "Monopol" the state tobacco warehouse in Skopje. Among 7,215 people who were detained in warehouses there were:

Further, the Jews were transported to the Bulgarian border with Romania on the river Danube, surrendering them to the Nazi German authorities and thus sending them to their deaths. As a result, the Jewish communities of Bulgarian-controlled Yugoslavia and Greece were almost completely wiped out. There was much harsh treatment before the Jews were transported in German cattle-cars to Treblinka. A few dozen Bitola Jews managed to avoid deportation, and four escaped from the transit camp. None of the 3,276 Jews of Bitola deported to Treblinka survived. In 2003, one Jew remained in the city that had been home to a Sephardic community for more than 400 years. Štip's ancient Jewish community was also completely destroyed.