Here's the problem as I see it. He owes $12 Mil. Its $5.5 mil for 2012 and 6.5mil for 2013...or something like that.
Even if he works his tail off and tours all year in 2014 and makes/nets, say, $20 mil. He can pay the $12 mil to the IRS. But that doesn't account for the taxes he'll owe for 2014. If Lil Wayne is at zero dollars right now, he'll have to earn enough to pay the IRS back, and then he'll have to pay taxes on what he earned because those earnings get taxed seperately. In otherwords, he can't just earn $13 mil and pay the $12 mil back to the IRS. Because if he earns $13 mil, then he has to pay taxes on that.
In otherwords, he's going to be perpetually behind unless he humbles himself, gets a modest crib, stops drinking champagne and start drinking budweiser like the rest of us, pawn the jewelry, sell the Ferrarri/Lamborgini and live a regular life.