So you employed a contractor to roof your flat roofed building who you knew was not insured to do any type of commercial flat roofing work, only shingle residential. You also know contractor only deals in cash, uses undocumented workers, does not 1099 any sub contractors, and cashes all checks at a currency exchange. This roofer also lies about his business income taxes, says he is broke and will declare bankruptcy.
Were you surprised the roof leaked?
You can sue this roofer. Probably it would be good to get the roof properly repaired, and pay the bill for the repairs, thereby establishing the amount of damages you have suffered. Remember to keep track of damage to the interior of the building, and any contents. Take pictures, and get written statements from people who inspect the roof.
Litigation of this sort is usually expensive, and it is not likely that you will be able to get a law firm to represent you on a contingent fee basis, given what you say you know about the defendant. It is more likely that you will be asked to sign a contract, and deposit a substantial amount to guarantee payment of court costs and attorneys fees going along.
If the company that did this work is properly formed and operated, you may not be able to reach the owner(s) personally, so their expensive home in Barrington may not be available to satisfy your claim.
If your claim is in Cook County, it may take 3 - 5 years to go to trial, so you should prepare yourself for that kind of wait for a decision.
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Sadly, while you might win and get a judgment against the company you hired, a general breach of contract debt is dischargeable in bk. If your claim against the company is based on more than a breach of contract (i.e. fraud) you might try to object to the discharge of such debt in bk court. As far as going after the owner individually, in certain cases, when a company lack certain attributes, such a capitalization or formalities, its possible to go after the owners individually. But you still have to consider if the owner is worth anything on paper, meaning can you actually collect a judgment. You might want to do some research first and see if he owns anything in his mane. Good Luck.
Your friend either didn't do his homework on this or took a major risk that didn't pay off for him. The state will pull this guy's license if you can prove that he worked outside the limits of his license, but if his company's really as close to the edge as you suggest, he'll bankrupt the claim and leave your friend holding the bag. I think this is a dead bang loser for your friend, but it's probably worth talking to a lawyer to see if there's any hope. One last avenue is to try and talk to the consumer fraud division of the AG's office. However, any complaint to the state or AG is likely to bring your friend's own business practices into question. Cash payments smack of money laundering or tax evasion and a hint of that to the AG can bring a prosecution down on your friend.