Describes the person, who gets the most unpleasant or difficult outcome in a situation. You can also say to draw the short straw.
Looks like I've got the short straw, I'm doing the late-shift while everyone else goes to the pub.
To milk it means to take full advantage of a situation usually to gain sympathy, respect or kindness. If someone faking it something to get the attention we say milking it.
Okay don't milk it, Sam, you've told me hundred times that you got tickets for the world cup final.
Sam had a week off with a cold, I think he is milking it now.
You have to expect the bad or unpleasant thing in the situation as well as the good thing.
Hey, Valeri, I got promoted
You have to take the rough with the smooth Sam, you can't have everything. Don't forget, you will work more