When did they go broke?
Lil Flip's parade of hits from 2003-05 now feels a relic from a bygone era: synthetic acoustic guitars! Harmonizing R&B divas! There's no market for "thug love" ballads anymore, which makes Flip shit out of luck. In 2007, the erstwhile Freestyle King was arrested for credit card fraud. Then, in a widely-circulated '09 email penned by the estranged mother of Flip's stepdaughter, it was revealed that he pays just $500 a month in child support. Since child support is usually tied to income, we can infer that Flip has fallen on hard times.
Did they recover?
Flip has faded into such obscurity that little seems to be known about his whereabouts year to year, but last Christmas, he was pinched for gun and weed possession. He pleaded not guilty last week and his pre-trial has been set for April. He also somewhat pathetically dissed Chief Keef, perhaps because Keef's "Love Sosa" chorus ("You boys ain't makin' no dough!") hit too close to home.