He really got drunk knowing he bribed people to rape his crush...yikes

Are you sure it's really a crush it seemed more interested in the competition

They weren't paid to rape her, just threaten her so he could come play hero, but when he didn't show, they decided to expand on the deal. I'm betting he did it right after she turned him down again and before he introduced the ML, but then when he saw them 'fall in love' right in front of his eyes, he started drinking. That said... yeah. Seriously, dude. That plan was messed up regardless.