This essay explores the economical and social paradigms surrounding one of the most influential Nordic border dynastic noble families in the second half of the fifteenth century - the Axelsson Totts. How mercantile possibilities and opportunities offered to them, reflected on their political actions and social bands. The Axelsson brothers of the Tott Dynasty would become of one of the most powerful noble families within the Nordic Union between 1444 och 1487. Axel Pedersen (Tott) would through well chosen marriage alliances into the noble families of both Denmark and Sweden, and with political prowess lay the foundation for one of the most dynamic family empires of the fifteenth century. In the year 1442, the Axelsson brothers swore loyalty to each other; to protect and defend their mercantile and economical interests in Denmark and Sweden. They would eventually control the trading routes in the border areas of the Union, and by exploiting the political chaos within the Union they would gain access and influence to the land trading routes for export and import within the Union and the shipping export routes in the Baltic Sea allowing them access to the Russian market through Finland and Estonia. The island of Gotland, with its tactical and important geographical position in the Baltic Sea became the key to the Nordic Union. Olof Axelsson (Tott) sailing under the Danish flag took possession of Gotland in 1449. Although technically a part of the Danish kingdom, in practice the island would remain independent and under the control of the Axelsson brothers until 1487 when the last surviving brother, Sir Ivar relinquished his rights to Gotland in favor of the Danish monarch, King Hans. The Axelsson brothers (Tott) would hold the key to The Nordic Union for almost four decades. Thus controlling the future of the union within the family by marriage, by political associations within and outside of the Union and most importantly by creating an economical empire based on personal family politics and border gentry aspirations.