The subjects of Jewish identity and Jewish communal vitality, and how they may be conceptualized and measured, are the topics of lively debate among scholars of contemporary Jewry (DellaPergola 2015, 2020; Kosmin 2022; Pew Research Center 2021; Phillips 2022). Complicating matters, there appears to be a disconnect between the broadly accepted claim that comparative analysis yields richer understanding of Jewish communities (Cooperman 2016; Weinfeld 2020) and the reality that the preponderance of that research focuses on discrete communities. This paper examines the five largest English-speaking Jewish communities in the diaspora: the United States of America (US) (population 6,000,000), Canada (population 393,500), the United Kingdom (UK) (population 292,000), Australia (population 118,000), and South Africa (population 52,000) (DellaPergola 2022). A comparison of the five communities’ levels of Jewish engagement, and the identification of factors shaping these differences, are the main objectives of this paper. The paper first outlines conceptual and methodological issues involved in the study of contemporary Jewry; hierarchical linear modeling is proposed as the suitable statistical approach for this analysis, and ethnocultural and religious capital are promoted as suitable measures for studying Jewish engagement. Secondly, a contextualizing historical and sociodemographic overview of the five communities is presented, highlighting attributes which the communities have in common, and those which differentiate them. Statistical methods are then utilized to develop measures of Jewish capital, and to identify explanatory factors shaping the differences between these five communities in these measures of Jewish capital. To further the research agenda of communal and transnational research, this paper concludes by identifying questions that are unique to the individual communities studied, with a brief exploration of subjects that Jewish communities often neglect to examine and are encouraged to consider. This paper demonstrates the merits of comparative analysis and highlights practical and conceptual implications for future Jewish communal research.