As far as I am concerned, Diogenes is not much of a philosopher. He is a philosophical figure. He is embedded in the popular imagination as a figure somewhat adjacent to his philosophy, but somehow apart from it. Ask people what Diogenes actually taught, what his words were. We have seemingly so much recorded from the philosophers of that era, but no one can really recite a line from Diogenes of Sinope. But everyone knows the anecdotes and perhaps tall tales of Diogenes, right? We all know about how he was able to humble even the Great Alexander.
For those that don’t, Diogenes was an ancient philosopher who lived as a contemporary of Plato and Aristotle, and who was largely a societal pain in the ass. Living in a way that reminds us all of modern homelessness, Diogenes lived in the streets of various Ancient Greek cities, famously living in a barrel. He flouted societal norms also in famously living with the barest necessities, having been both a free man and a slave in the course of his life. Going through his list of life anecdotes would go against the point of this review, but if you are not familiar with these anecdotes, they are surely worth looking up, if nothing else for how entertaining they are.
What we have from antiquity we have because of good or ill fortune, with an editing hand from a medieval Catholic church that tended to keep ancient text mostly based on to what extent it could be spun to fit into a catholic world view (and, occasionally to preserve an ancient classical grammatical form that appears in their work, as was once explained to me about some of the surviving works of Martial and Juvenal).
Jean-Manuel Roubineau short book is a pretty nice overview of what we know about Diogenes, why we know it, and how it connects to the thoughts of the time Diogenes lived in, and some of the wider implications of his work on what came after him. Short is the operative word, as there doesn’t seem to be all that much about him, but it was nice to get something of a more rigorous biography about him, as well the contextualization of his thoughts in the Hellenic world.
I think this book teaches that Diogenes actually is a philosopher, should one want to do the work of uncovering his thoughts. But it still doesn’t mean that there is much philosophy to that philosopher, and the major work cited seems to almost exclusively be the biographer Diogenes Laertius. It is perhaps one for my reading list in the near future.