I'm calling it now; Ain (or duke Selleg) is responsible for the destruction of Michele's family.
The manga is full of foreshadowing such as:
1) A unknown noble (probably the Duke) appears in Michele memories (when he's sipping tea at a gazebo)
2) Ain states that the Duke likes using traps and waiting for his prey to fall
3) All of chapter 16 is pretty damning, specifically when Ain proposes to take care of the injured rabbit instead of killing it, suggesting that Michele could gain the rabbit eternal affection now that the animal was injured and broken
4) The title of the manhwa itself is pretty on the nose: 'The Taming' (in this case, the taming of Michele)
My theory: Somehow, Ain wanted Michele for himself since way back, so he killed the first son, made the second son incurr in a monstrous debt and 'helped' the third son elope to get to marry Michele. Why? Because if the family wasn't destroyed he couldn't sweep in and 'rescue' Michele (buy him). If the family was ok, Michele would have ended married to a daughter of any other family and the psycho bas**** couldn't have that.
Thanks for coming to my TED talk lol 😂