Tails claims that Sonic spent all of his money on coke and Dreamcast stock (though Sonic says that Tails is the one who gave him that stock). Sometime after Season One, Tails ended up in a coma because he drove off the Tornado while drunk and is unable to get Sonic a job until he recovers from his injuries. In "Excite Bike", Sonic makes it worse by driving his bike straight into Tails by accident and then leaves his hospital TV on a show marathon that Tails dislikes. Tails recovers in "Toad" and is used as a threat to Sonic by Mario, telling him that if he failed a job then Tails would be executed but Sonic replies that it's not a threat to him at all. According to Sonic in "The Battle Part 01", he values his poster more than Tails's life and that he tells him this everytime. But never the less, Tails helped Sonic in his battle against Mario by killing Dr. Wily.
Tails has become a pretty successful person financially after bankrupting Sonic when he bought Dreamcast stock. Tails claims to have a drinking problem that he believes he can control, however, it sometimes overpowers him. Tails had "The Tornado", his own plane that he made, until he crashed it while under the influence. Tails' favorite shows are Little House on the Prairie and Bachelor Pad. While Sonic was working for Mario, Tails somehow managed to DVR numerous episodes of Bachelor Pad without Mario noticing. Tails knows that Sonic truly doesn't care about him, after saying that, "Yeah, no, he's right. He wouldn't give a shit if I ever die..."
Drinking Problem Subsided
Tails claimed to have a drinking problem in Season 2 premiere, "ExciteBike". He had crashed the Tornado while he was drunk. He has since stopped drinking as seen in many episodes where Sonic, Eggman, or the others have been drinking and Tails was not. Season 3 episode "Link" is a perfect example because Link wanted to take the guys to Margarita Manor, Tails refused and told Sonic that they needed to focus on their job to find Princess Peach. When Link tricked them to going to the Margarita Manor anyway, Sonic and the others started chanting and went into a frenzy, Tails was immediately irritated by their immaturity and shouted "I hate you, I f***ing hate all of you!".
In the finale of season 3 Tails blows up the money Sonic and his crew have collected through the season, in retaliation of all the abuse Sonic had given him. In Season 4, he goes on to become wealthy and arrogant, the star of his latest video game Cash Explosion, and becomes Sonic's new arch-nemesis. At the end of season 4, everyone gets blown into space and Sonic starts treating Tails like normal again.