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The Light Novel series is the source material for the adaptation of the Anime and Manga series. The information and terminology on the article will be based on the source material rather than the adaptions.
Oswald began as a very laid back person. Only when his position came under threat due to Wilfried's shortcomings, he began to become serious about his work. Prior to her imprisonment he was deeply loyal towards Veronica. He holds the belief that Wilfried takes precedence over all other archduke candidates, so that other archduke candidates should be giving Wilfried support and credit even at their own expenses.
Oswald, like all of Wilfried's original attendants, was selected by Veronica. While it was not explained how he is related to the archduke's family, Rihyarda mentioned that he was of archduke's blood and this along with his status of archnoble was a significant deciding factor in him being chosen as Wilfried's head-attendant, since it would give him the position necessary to handle Wilfried and even literally tie him to a chair and force him to learn, should it become necessary.
Florencia had also trusted Oswald to counteract Veronica's presence to some degree. However, since Wilfried had been selected as heir, neither Oswald nor any his attendants punished or restricted Wilfried in any meaningful way, either believing that the risk of offending the future archduke was not worth it, or just being plain lazy. This lead to Wilfried acting like a brat and not understanding the world of nobles.
Oswald began as a very casual person; however, when Rozemyne traded places with Wilfried for a day he was quickly put under pressure to perform in order to keep his job. Since then he has taken his position much more seriously and has begun planning with the other attendants how to ensure Wilfried remains the heir.