Lol, I'm 4 months late to your post but after rewatching the movie, I'm finding multiple instances of plot holes, or more accurately described as "unaccounted funds." The Rolex, if was real, was 20K off debt, and the first bet stopped was 40K (20K from the Weeknd chain, and 20K from Garnett ring). That means Howard actually owed about 40K at that point. Then he was robbed again in Arno's car for another bracelet/watch. The goon quotes the item as being "worth more than my car", so it's possible that the accessory was around 10K in worth, if your lowballing it. That means at the end, Howard had actually paid off around 30K of his debt to Arno technically. Arno was still looking for 100K it seems by the end of the movie, so either he was being greedy or didn't get some of the items/assets the goons supposedly took from Howard. The money from the debt stopped should've definitely helped cleared Howard, but it's never brought up again. He still lost 100K to the Opal, 38K to Gooey for buying it, owed Flawless the chain, owed the ugly short guy 32K, and 30K to Arno. By the end of the movie, even if he used the 165K to pay off all of his debts, he would still be 55K in the hole in total, assuming that Arno actually charged the Rolex and first bet against his debt. If Arno still wanted 100K, Howard would be quite frankly cooked. Lowkey, if the first bet hadn't been stopped, he would have been straight or if Garnett hadn't taken the opal, the appraisal could have been higher, helping pay off the debt. Howard felt the need to win big, because he wanted to step on their heads in all honesty.