Yes, because the Hutts would be totally cool with a couple of Jedi rolling up to their gambling dens and blatantly cheating for several hours. Screwing over one random used car salesman on a single bet is much easier to get away with.
Not to mention the whole "he could be the chosen one" angle, at which point freeing Anakin was just as important to Qui-Gon as getting off-planet.
Qui-Gon is gambling at much higher stakes, placing the fate of the entire future of the galaxy into the hands of that boy, who Yoda had strongly recommended against being trained. So it's not that Qui-Gon was against Obi-Wan wanting to gamble, he just wanted him to significantly up his game:-).
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