So a person I knew came into my room and grabbed two items totalling about 140$. He told me that he took them because I supposedly owe him 100$ on a poker site, in which I lost money that he had won on my poker account. Do I have any legal recourse that I can take? I have two witnesses to him taking my things from my room.

Yes, he cannot take your possessions because he owes you a debt, he doesn't have that power. You may owe him money, but that does not give him the right to take your items, that is theft. Call him and tell him you are pressing charges if the items are not returned in 24 hours.

If this were to go to court, would it be possible that I be ordered to pay the 100$ that I owe him from the poker account?

I really don't think so, if the account was your account and you lost money he had won on YOUR account, technically you just lost your own money, not "his" and even if it was his, which it wouldn't be if it was made on YOUR account, he still has no right to take your things.

Let me get this straight, He won some money using your account and then you lost it? If so, then he has no recourse because it can't prove it was his money. And he has no right to take your belongings.

Well, the only catch is that he had started playing some on the account and lost, so he did pay me for the amount that he lost. I think it was about 40$. Then, he started winning and I continued to play on the account, to which I lost everything that was on the account. So it wasn't completely my money that he was playing with, since he lost 40$.

By the way, I told him about contacting the police and I think he's getting a bit scared. He now wants 50$ in return for my belongings. At this point, he's just irritated me to the point where I just won't give him a dime for my stuff back.

Legally he doesn't have a leg to stand on since its your account. Morally, if you lost money he built up then you would have an obligation to reimburse.

Ok I've made a settlement with the guy. I'm willing to give the 40 he gave when he lost money, and he's agreed to give the belongings back. I guess that would be the moral thing to do.

But the 40 he gave you was YOUR money that he lost, not HIS money that he lost. I'd just tell him to give back the stuff or you're calling the cops, 'cause no way is he in any way entitled to any of the money won OR lost on YOUR account.

I disagree with Charlotte. If he won money while playing and then you played with his money and lost it, then you do have a moral obligation to repay. Sounds like a reasonable settlement.

If you owe him the money, then yes, you can sue him but he could sue you, So from a moral standpoint, he should pay you back for your property, and you should pay him back for the money you lost.

Now if gambling is illegal where you live, most likely your online gambling is illegal also, and you can not sue for illegally gained funds.

Sounds like perosnally both of you need to grow up and take repsoniblity for your actions.