Legal Question in Business Law in Massachusetts

Re: He owes me $2500.00

I disagree somewhat with my colleague / peer, Lawrence Graves.

Small claims court is limited to $2,000, I believe, so you would lose $500 right off the bat there. Secondly, you run the following risk: if you lose (and the burden of proof is upon you!), you cannot appeal. However, if you win, HE CAN appeal! Third point is that you don't really see a JUDGE in small claims, only a clerk / magistrate who is usually not even a lawyer and, well, I'm not supposed to disparage any part of the justice system so I won't! But I will add that if you go in front of a clerk / magistrate WITH a lawyer, you're pretty well off and more likely to win but still subject to appeal.

However, any reasonable attorney is going to want to get paid "up front" -- at least as a retainer even if it is contingent upon getting the judgment, rarely will you find an attorney willing to make his fee contingent upon getting the amount collected, though, which means you could have paid an attorney, say, $1,000, and still not have a dime actually collected.

Does he have assets you can attach (if you manage not to spill the beans and warn him)?

What evidence do you have that he ever got any of your money? Did you pay him by check, at least?

By the way, he's not in the investment trade in any way, is he? (Does he have any sort of investor's license, like a broker or registered representative? If so, there's another approach for you to take.

I agree with Atty Graves that you are unlikely to get your attorney's fees paid by him even if he loses, whether you go to small claims or to District Court. It's prhoibited in Small Claims and only rarely permitted in District Court; in Superior Court (which you can't use for this), it's permitted but under unusual circumstances.

Did he lose the money in the market? Did he spend it or is he just holding out on you and hiding it from you?

Good luck. Let me know if I can help you.

Re: He owes me $2500.00

Three words of advice: Small Claims Court.

You don't have to hire an attorney, and you are unlikely to recover attorneys' fees if you do.