This paper examines the interrelated issues of time and money in club and international football. Specifically, the focus is on small Caribbean countries and territories that are rich in talent, but poor in opportunities. In the past decade, several professional teams in the Caribbean have played in the minor league system in North America, but have been stifled by several factors. This paper argues that the creation of a ‘Caribbean division’ that plays in either the North American Soccer League (NASL) or United Soccer League (USL)-Pro league would enrich and develop teams and players from all parties involved, and they would be more competitive in FIFA World Cup qualifying. The key ingredient is correctly timing such a venture.