Dear ejensen,
It's a doozy all right. The classic Canadian Sweepstakes Scam informs the mark they've won a Canadian sweepstakes but must first pay some kind of a tax in order to collect. This con evolved from The Nigerian Letter Scam, which for at least 20 years has been announcing to potential pigeons that this foreign country's slush fund needs their particular bank account in which to snuggle into. Then, after many faxes back and forth, it turns out the one per cent tax must be paid in order for the transaction to take place.
And THAT con evolved from 1588's Spanish Prisoner Game in which an Englishman was asked to pay the ransom of a wealthy countryman so that that gent might escape wicked King Philip II of Spain. In return, the newly ransomed and his delectable daughter would be mighty grateful, wink, wink, if you get my drift.
Your guys are throwing in a bit of The Badge Scam to make it their own. The Badge Scam happens after a Pigeon Drop or Bank Examiner Scam or some other con in which the victim has handed $5,000 over to a stranger in a parking lot and come to realize that wasn't such a hot idea. Next, he gets a call from a "cop" who says he knows all about that awful deed, but in order for the pigeon to get his money bank, once again, he must meet "their man" to recreate the transaction.
That they asked you to make the cashier's check out to another party is just another attempt to muddy waters already churning with international red tape. And I'll bet circumstances change so that the tax must be paid before you actually receive anything.
As for how they got Tim's name, either they are the very sweepstakes people, or the first con artists sold their "sucker list" to the second.
I hate to use this column for obvious self-promotion, but if not now, when? These and other scams you will find in my book, Rip-off, published by Writers Digest.