Potentially -- this is almost exactly how Pachinko parlors in Japan operate, with non-cash prizes being given out, but with "known" nearby establishments (sometime located in the same physical building) that will buy them for cash. Other options include the giving of vouchers/gift cards as prizes.
Whether this is legal or not is a question of if the buyer is "truly" acting independent of the gambling establishment. The general legal term for this is "arm's length transactions".
A completely unrelated organization is presumed to be acting in its own best interest, in an "arm's length" manner, though this can be overcome with evidence of collusion. If the casino is willing to "buy back" its marker at a given price (much like Las Vegas casinos are required to do), this can be done with independent intermediary negotiators in a legitimate arm's length transaction.
In the Japan example above a "three-shop system" of nominally independent shops circle goods between them to effectively "legalize" (or at least not draw the ire of authorities over) cash gambling payouts.