Someone owes me money

[Gamblor]

I've known a guy, "Adam" for about 8 months. He introduced me to the underground Toronto poker scene and basically has been fully prepared to front me money, upwards of $1500, to play. I have always been punctual about paying him back. We have a cordial relationship, he's helped me with my game, I've done the same with him.

One day, he asked to borrow, on behalf of someone else, "Jimmy", I barely know, a significant sum of money to help get him back on his feet after. It wasn't life-changing, as my bankroll was healthy at the time (and still is), but $5000 is significant and I do want it back. Adam vouched for Jimmy, who is apparently loaded but fallen on hard times, and promised to back the loan.

Jimmy drives a Mercedes SL500.

I've asked a couple times over the last 3 months and have always received an excuse... early on, when the loan hadn't been paid, he put me into a couple large tournaments at $250 a pop.

5 months have passed.

"We're waiting for an investment to come through."
"Jimmy owes other people as well and is remortgaging his house at the beginning of may"

I've confronted Jimmy, who has recently opened his own poker room. He gave me his phone number, and promised to have the money ready for me tonight.

I've called him today, he hasn't picked up the phone and has no answering machine.

Other things:

A good friend is helping Jimmy start up this room.

The original friend is a tournament director who basically runs every tournament in the city, tournaments I've been to and would like to go to again. Jimmy is also a member of the Italian community in Toronto. I don't know if that's in fact significant or not, but it might be.

I have a friend, "Peter", who is a pimp. like, a real live pimp. he's a good guy. however, he has a friend, "Greg" who basically handles all of his "loans". This ain't playin around. Greg has offered to help me recall the loan using whatever means I allow or prohibit.

My current plan is to show up tonight to Jimmy's club and if I'm not paid back, to give Greg a call, with the stipulation that he is not permitted to do anything that will get me or him in trouble with the law (Jimmy, of course, doesn't need to know that stipulation).

Any better suggestions?

Am I better off going after Adam?

I don't intend to lend $ this big ever again, that's for sure.