This Editorial has the objective to present the Thematic Section (TS), that derives from selected papers, that were presented during SIDREA International Workshop - May 19th 2020-2-5pm. It is structured in two sections. The first section is introducing the contents of the ST. The second section discusses the multifacted phenomenon of trust in business organizations with special reference to controversial industries including gambling and different trust profiles are (i.e., non-confidence, negative trust, and distrust, and the corresponding social categorizations).