He kept on "reducing complexity" while re-building what is essentially the same, rather primitive, language. ANd he kept throwing the baby out with the bathwater.
One of the Oberons had three different loop constructs, and only one of those could be terminated early. Because reasons. Then a newer Oberon reduced the number of loop constructs, but also removed the ability to terminate them early. Then a newer Oberon... ad infinitum.
And you can see it in all the langage variants he built: he insisted that the core of the language be small at the expense of usefulness to the point of uselessness. And purely irrational academic fixation (such as function vs. procedure or the aforementioned loops).
Was he instrumental in creating a good teaching language, and one of the first good high-level languages (Modula/Pascal)? Yes. Did he do anything noteworthy after that? I honestly doubt it as he was pursuing this idree fixe of a "small language where you can remove nothing more".