He was first met in the story "Casino Night". Thanks to the Marxio Brothers hypnotic machinery, he'd gambled away his entire savings and even his house. He was left wondering how to explain this to his family. When Sonic arrived, the dog was shocked that he'd come so far into Robotnik-controlled territory.
Many years later, in "Bitten by the Gambling Bug", he would be seen again. He was once again shirtless and destitute, despite the lack of hypnotic devices in the Zone.
Later, in "Ultimatum", he'd actually received a winning ticket! However, he would be distracted (along with most of the casino) by an ultimatum delivered by a villainous "Sonic" and while he was watching that, someone stole his ticket.