If you want to argue DD got good or better value for the prospects he gave up, that’s one thing. But the notion that no one he gave up has worked out is a complete fallacy.
Michael Kopech is currently closing for the Dodgers in the postseason. Santiago Espinal was an All Star. Mauricio Dubon and Jalen Beeks have both carved out decent careers.
Also, while not prospects, certainly Travis Shaw and Wade Miley both went on to far more successful careers than the players acquired for them (Tyler Thornburg and Carson Smith), who were both complete flops. Yet, like the Chris Sale trade, both deals made sense at the time…