When did they go broke?
Fat Joe once rhymed about being turned on by "office types." He could use some business acumen himself. In 2010, it was widely reported that he'd been hit with a $139,000 tax lien. Joe told a journalist at the time that he was "perfectly perfect," which was too rosy a description to be anything other than shitkick.

Did they recover?
No. Contrarily, things have only gotten worse for Joe—it turns out that he's stolen more than just Pun's rhyme book. Last December, he admitted having failed to pay income taxes on $3 million between 2007 and 2010. The rapper, who is expected to be sentenced in April, is looking down the barrel at two years in prison.