Buta Kizoku wa Mirai wo Kiri Hiraku you desu - Ch. 7 - After the Duel

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Not really. He needed to fight in a pretty dirty manner and totally outside of Merlon's expectations to win. And even so he only won through self-sacrifice since he basically could eat more pain than Merlon. That's also understandable since Herbert was fighting with the weight of his whole future life on his shoulders. Merlon was only fighting to finally give a scumbag a much needed lesson.
The problem is I feel like we need to see the protagonist actually suffer a bit for his long period of being awful and trul reflect on it. It makes the attempt at redemption less impactful when it immediately succeeds rather than having setbacks, especially set it was put in motion by a deus ex machina letter from the future. He picked the fight out of his own hubris and cruelty, and sure he trained hard for a couple days but that's really not very much. It's a mistake he made. He should have paid for it.

Nobody would have listened to him. They only listened to him after the victory because they were shocked silent. And because the winner gets to speak.
Yes, that is the point. Most people wouldn't have listened to him, but a small handful might have noticed. Part of what makes redemption stories good is an earnest effort even through setback. But like I said, this is also a monthyl and probably wants to go at a higher pace so it takes these shortcuts.
 
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The problem is I feel like we need to see the protagonist actually suffer a bit for his long period of being awful and trul reflect on it. It makes the attempt at redemption less impactful when it immediately succeeds rather than having setbacks, especially set it was put in motion by a deus ex machina letter from the future. He picked the fight out of his own hubris and cruelty, and sure he trained hard for a couple days but that's really not very much. It's a mistake he made. He should have paid for it.
He has actually suffered longer than the little while before and after the duel. It's because he has been living in self-loathing and depression for a few years already, only masking it by excuses, acting arrogant, and being a bully. That's actually a rather common reason for bullies to be bullies: their own life sucks. Of course not a universal reason, but a common one. It definitely is for Herbert. He's suffering from his friendlessness as well, so he kept telling himself that since he's the son of a mighty ducal family, he doesn't need friends. Ironically it looks like his sycophants could have been real friends if he had got his act together.
 

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