The demand for higher education and research in economic, commercial, and legal fields for corporate, professional, and institutional activities between Florence, Prato and Pistoia was already intense when the Faculties of Economy and Management and of Law started their activity in Florence in the 1920s. Such demand has been growing in the following decades till the present-days. This chapter discusses how opportunities and difficulties for fruitful exchanges have evolved in these fields: first, considering the changing didactic offers of the two faculties, with their possible contribution to operative skills and bases of cultural progress for the local systems; and then, moving on to a deeper discussion based on leading figures of the two Faculties in the second half of the 20th century.