This study deals with Vittorio Checcucci’s ideas and proposals as to mathematics education. The scopes of this work are twofold: 1) the first scope is historical: my aim is to reconstruct Checcucci’s thought. This is a novelty because almost no contribution dedicated to Checcucci exists. The few existing contributions are brief articles whose aim is not to provide a general picture of his ideas; 2) the second scope is connected to mathematics education in the 21st century. A series of argumentations will be proposed to prove that many Checcucci’s ideas could be fruitfully exploited nowadays. For the first time, the thought of this mathematician is exposed to non-Italian readers because his ideas are worthy to be known, rethought and discussed in an international context.