The research aims to substantiate the existing need and real opportunity for the countries of the Caribbean and Latin America to transform and implement a completely new and improved model of economic development, which would be based on digital development. During the research, the authors applied such research methods as historical and graphical comparison, tabular analysis, and grouping. The methods applied in this research aim to assess the results of the economic development of countries examined by the authors for 2017–2022 through institutional and economic generalizations. The authors focus on Latin American countries and Russia, highlighting the economic challenges Latin America has faced in recent decades. Achieving a new level of economic growth and an economic breakthrough is possible with digitalization. However, this requires addressing economic and digital inequalities, including those on a regional level. The GDP analysis reveals that economic growth in Latin America is not directly influenced by specific economic models or by economic and political integration. Additionally, the assessment of digitalization progress, based on global indices, shows a catching-up trend, which has limited the region’s improvement in global rankings.