Here's what you have to do.
First, take Jack's resume, give it to whoever is in charge while the boss is away, admit that you're doing it as a favor to your roommate, and tell the truth about why you don't think he'd be a good hire. There's no reason to beat around the bush unless you want to look like someone who's easily manipulated.
Second, start treating each bottle your good booze like a girlfriend.
Suppose, for whatever reason, you had several attractive, intelligent, fit, Mustachian women who were into booty calls, and who wanted to hang out with you in a consensual, polyamorous, non-jealous way. You wouldn't even have to pay for dinner: all they want is to be loved and appreciated, and to enjoy the time they spend with you. So here you are with a short-term girlfriend, or two, or five, or however many bottles of good booze you have. Each is unique. Each is different. How would you deal with this situation?
What you're not going to do, is share. If a gorgeous woman was in lust with you, would you really set Jack up with her instead? No. You are a gentleman. So show some respect.
Acknowledge your girlfriends, invite them to your parties, and encourage them to socialize with your friends and family. Set aside intimate time with each of them one-on-one, and perhaps have a couple of three-ways if you really want to get your lips wet. But keep them from crossing Jack's path.
Jack knows your girlfriends exist, and he's clamoring to be set up with them because in his mind you've got more poon than you really need or can service. Yet that would be a waste of a sensitive, caring partner. So unless you've got some kind of masochistic cuckold fetish, fob Jack off with the alcoholic equivalent of the fugly wingwoman: the IPA perhaps, or the light beer. You've already made him a gift of it. Remind him of that.
In this way, you preserve your alpha status. Leave him only the leavings from your wildebeest kill, and make sure you take all the best bits for yourself.
O' the dishes... you're giving a fuck again. Either that, or your fucks simply like to weasel out of confinement and go yipping and baying after things that don't matter, like a poorly trained dog chasing a car. Find a way to contain this wayward fuck, and if you see it start to do the car chasing thing, kick it in the ribs. Then, it will momentarily become a flying fuck, but at least it will not be given.
Do your dishes, ignore Jack's, and if the stench is too terrible or it's attracting vermin, say so.