Your buddy is either a white metrosexual or a black gangster, 'cause that's who collect expensive watches. (Excluding Jewish pawn shop owners, of course.)
You already know how trading with whites works out, and if the dude's a black gangster, his entourage will steal it back at gunpoint when his next CD drop lands with a thud and he's got a 10k liquor bill to pay at the VIP room.
I'm poor but I believe you can get Rolexes for like $300-400. Those are probably the low end ones though. $1000 seems like a lot for a watch unless you're a one serpenter.
Buddy sounds like a drug addict pawning his shit for pennies for his next hit IMO. A good friend would just lend him the money so he can get his shit. This will be a friendship ender.
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Pumpy gives me the best advice.
You already know how trading with whites works out, and if the dude's a black gangster, his entourage will steal it back at gunpoint when his next CD drop lands with a thud and he's got a 10k liquor bill to pay at the VIP room.
Walk away, injun.
Beware the white man