I am sure Tony went up and down. Generally, he was probably netting huge sums. As seen many times. But he spends it just as soon as he gets it. So its an up and down roller coaster. Hes probably averaging about 6 million. But he starts to blow it all. But someone like him, can probably make it back in no time.

Plus, you have to remember, this show is still fiction. Everything that happens does not have to make sense. One moment the writers want you to think he has more money than he knows what to do with. The next, they want you to think hes in the hole for dramatic effect.