Roomate ex roommate wont pay/sign off lease - new roommates want on lease

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So one of our roommates (let's call him Mr. Roommate) decided to stop paying rent and move out. We disagreed at first, as he gave us a paper to sign which would release him from obligation of the lease as of the following Wednesday (which gave him a week to fully move out, clean, and pay us and allow for us to find a roommate). He had mentioned his wanting to move out before but never talked any final decisions to me until this day, (and even then he just left a sticky note on the document). So eventually we ended up saying that as long as he paid for the time he was still in our house, we would let him off the lease. Now he moved everything out (but left the room with a box of garbage, garbage all over the floor, and a couple miscellaneous items that he never came back for). He still hasn't paid us, still has the key, is still on the lease, and we have new roommates wanting on the lease. Mr. Roommate caused some damage when moving out, I told him he needed to cover it and he acknowledged that. Later (no more than a week after he moved the big things out, which was around mid Oct.), I tried calling him and he didn't pick up. I texted him asking when he was going to take care of the damage and finish this deal up. No response. Then a few days later, at night a tow truck guy knocked on my door and asked me if "the blue car over there" is mine. I said no. He asked if it was a roommates and I said no i dont think so (because Mr. Roommate's car is black). The tow truck guy said he needed to do his job and mark it for towing. Just in case, I called Mr. Roommate twice and didn't get ahold of him. The next morning at 7am I texted Mr. Roommate again, asking when he was going to pay us so we can get him off the lease. I also said that he really needs to move his car. (I said this just in case the tow truck guy was talking about Mr. Roommate's car because I had not yet gone outside to check). No response yet again. As it turns out, the car was his and it did get towed as my roommate and I found out as he. texted us both asking where his car was. My roommate texted back saying well did you leave it in the no parking zone? if you did, it was towed. that's the last we have heard from Mr. Roommate.

So, the next day I called Mr. Roommate just before I went to the rental agency we go through (to talk to them about clearing new roommates to move in) and he did not pick up, so I left a message saying that we need to talk and get this sorted out. No response. Now, we have our new roommates ready to move in, fully cleared, and all we need is for Mr. Roommate to be off the lease so that they can be put on the lease (which we cannot add them without Mr. Roommate's permission). I have written up a statement to mail to his work labeled, Mr. Roomate C/O [Job] stating the charges he owes us and requesting him to pay me, sign off the lease, and turn in the key. I charged him for the whole of october (since we'd agreed he would pay until he was out in oct. he never cleaned out his room or fixed the damage or even contacted us about it. so, come oct 31, i felt that he should pay because he was not fully out and had not communicated if he felt that he was.)
I don't know what to do now, though. I was going to send this statement to his work along with a paper that gets him off the lease. However, I don't want him to sign the paper letting him off the lease and then not get paid. The rental agency was going to send the bill for damages to him, which I will need to check and see if he has paid yet, and I will send the letter after I hear this verdict. I closed the letter with: "Please pay this amount to [my name], sign your name off the lease, send payment of $132 for damages to [rental agency] (if you have not done so already), and turn in your key."

So, essentially what I am asking is: is Mr. Roommate still liable to pay for everything he owes me as of oct 31 if i sign him off the lease? Also, what are my options if he refuses to pay and/or refuses to sign off the lease?
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Mr. Roommate not only owes rent for October but the clock continues to run on him for November...and, as long as he doesn't sign off on the lease his financial obligation will continue until the lease ends.

This is especially true since it appears you are "stuck" in terms of adding new tenants until he signs off on the lease.

He isn't doing this because he has no intention of paying for either back rent or damages. He is hoping that you will just go away.

The only hope you have is 1. that the landlord/management go through the process of evicting him, thus "clearing" you to add the new tenants or 2. you begin the process of suing him for his share of the owed rent plus damages.

I sent a letter to Mr. Roommate, giving his charges as of Oct. 31, 2009. However, I have yet to hear a response. All I have gotten is a text asking if he is off the lease yet and I said he needs to pay first. I have since tried to contact him and am yet unable.
I also have an added complication. In his attempts at freeing himself of all obligations, he has started rumors and things about our other roommate, saying he was doing drugs in the house. I have not witnessed this, but I am unsure if Mr. Roommate has proof of some kind, or a friend that is willing to be a witness. (He has family in his line of work and the other roommate worked there and got fired because of Mr. Roommate, thus Mr. Roommate has authority and possibly friends in authority that will be willing to say that this third roommate did drugs).

Would this change my case? Mr. Roommate told me that he wanted the garage to himself and that we owned too much stuff when he said he wanted to move out (presumably the main reasons why he wanted out). Then, after I wouldn't agree to signing him off the lease before he moves out and pays, he began claiming his drug story. (However, I know Mr. Roommate did drugs in the house, too, but they were less harsh than the ones he is claiming roommate #3 was doing).
I dont want to get involved with the drug issue, but if Mr. Roommate brings up his accusations in court, I am wondering if that would cause me to lose my case or be grounds for countersue or eviction.. Roommate #3 probably wouldn't go to the court case if I went to small claims court.
Do you have any advice for this predicament?
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He won't sign off the lease, though. That's part of the problem.The rental place won't take him off the lease until he notifies them. So, I don't know what I can do about that.
I have another concern. If I sue him and he still refuses to sign off of the lease, am I still stuck with him on the lease? It turns month to month in May. What can I do if he still won't sign off? My rental leasing agency I go through said the only way to get him off the lease is to get all of ourselves evicted.

also, if I do sue him, do I only sue him up to present or for the amount of money up to the end of the lease?
I have another concern. If I sue him and he still refuses to sign off of the lease, am I still stuck with him on the lease? It turns month to month in May. What can I do if he still won't sign off? My rental leasing agency I go through said the only way to get him off the lease is to get all of ourselves evicted.

also, if I do sue him, do I only sue him up to present or for the amount of money up to the end of the lease?

Your situation is too complicated for a short answer on this forum.
Anyone can sue anyone else.
If you sue him, you'll win.
If you win the suit, he can be legally taken off the lease.
But, you will need an attorney to make sure this is done correctly.
You should retain the services of a local attorney.
Mr. Roommate appears to be a jerk.
Jerks can make other people's lives difficult.
Mr. Roomate needs to be dealt with in a court of law, not an internet forum.
You started this thread almost four months ago.
You should get cracking on this ASAP, otherwise May will have arrived and you'll have made no progress!
I decided to sue up until the end of the lease since I know that it will probably take about that much time to deal with all of this. Attorneys can be expensive. From what I have looked up, often $100-$300 per hour. Yes, I know this needs to be dealt with in a court of law. But I am asking for advice online because that's what this site is for. I have already filed for small claims court, but now he is taking advantage of trial by jury. In the notification I received, it suggested I hire an attorney. But I don't want to do that if it ends up costing more than it is worth. I also don't know if he is using an attorney or not. So yes, I am taking action, but my situation remains difficult. I need to decide within 2 weeks whether or not to take him to court still, which I am pretty sure I will do. Now, my question is, will an attorney be worth the money or can I do this without one?
I'd let it go.

It'll cost more than what you might gain.

You do know, that even if you prevail in court, you won't get your money!

All you'll have is a piece of paper saying he owes you X dollars.

You'll then have to find creative and legal ways to get the money from him!

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