|"Does this hat make me look more credible?"|
The main problem with this story is that the penalty for not having insurance isn't being assessed until 2014 returns are filed a year from now. But some Republican apologists tried to point out that perhaps Drudge had decided to estimated his 2014 income and thus pre-pay both his tax and the penalty a full year in advance. But those GOPers also failed to do their research-- oops! The IRS hasn't updated its forms yet for reporting the penalty-- so if Drudge had pre-paid his 2014 taxes and included the penalty, the IRS would have treated the entire amount as pre-paid tax, since there is no place to itemize the penalty amount.
After much public skepticism of his original story, Drudge later tweeted (in two messages, both now deleted) that he had been forced to pay the penalty because of quarterly filings. But that story doesn't hold water either, since the penalty for businesses with under 100 employees was delayed until 2016. But wait-- maybe the Drudge Report employs over 100 people (not according to Wikipedia, he doesn't) . . . hmmm, running out of stories here . . . maybe he's filing quarterly as an individual (really?) and then adding a penalty to his quarterly tax payments---but as we've already established, federal tax forms haven't been updated, so the IRS would treat any prepayments as tax payments. I'm calling bullshit on this whole thing.