whats the saddest thing you've ever had to do?

Okay, so there has been a sick raccoon wandering my roommates(parents) property for the past 5 days, just walking around during the daylight. our family dogs(a mini Yorkie and a mixed Collie and shepherd) yesterday attacked the raccoon. but, it didn't do anything except lay on its back and hiss and cry. but they stopped the fight and shooed it away. anyways, Just a little bit ago my dad had me take the .22 out and end his misery(i volunteered for the mission because, every other man in the family has killed an animal in some way, so i figured this could be my chance to show my father i am not a pussy, and plus i just wanted to shoot the gun) .... I was about 10 feet away from it, and it was just sitting next to our pond and looked up at me and we locked eyes, almost like it knew what was about to happen.... saddest fucking thing I've ever had to do in my life... then i realized i missed the first shot and couldn't aim for shit and took 5 shots total to kill it. i wanted to puke.

TL;DR sick raccoon on property, takes .22 and shoots it while it locks eyes with me. took 5 shots to finally kill it.