- The Washington Times - Saturday, March 22, 2014

Left leaning media outlets criticized Internet news mogul Matt Drudge’s tweets on Friday, but the backlash stemmed from a misunderstanding of how Obamacare will affect small businesses.

On Friday, Matt Drudge tweeted, “Just paid the Obamacare penalty for not ‘getting covered’… I’M CALLING IT A LIBERTY TAX!”

A few minutes later, Jesse Lee, the Director of Progressive Media at the White House, tweeted a response, saying Mr. Drudge’s tweet was a, “flat lie, no fee for previous year. Scary how much influence he once had.”


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From there, the tweets came rolling in, attacking Mr. Drudge via social media and liberal news outlets, Breitbart reported.

“Dude, there’s no penalty until next yr,” Sahil Kapur of Talking Points Memo tweeted, followed with a full story in the news outlet with a headline saying Mr. Drudge was “probably lying.”

“Americans don’t pay a penalty for not having health insurance until they file their 2014 taxes—in 2014,” Dylan Scott wrote in the story. “So either Drudge is lying or he paid a huge penalty a year earlier than he needed to.”

A similar story appeared in Huffington Post, in which the author, Jeffrey Young, wrote Mr. Drudge’s tweet was “weird” and a “little head-scratching.”

What each critical tweeter and pundit failed to realize was that Mr. Drudge, as the self-employed proprietor of The Drudge Report, files taxes as a small business on a quarterly basis.

The IRS requires self-employed business owners to file annual returns and pay estimated quarterly taxes. When entrepreneurs like Mr. Drudge file their 2014 first quarter taxes, they have to pay the individual health care mandate if they are not getting Obamacare coverage.

The IRS form also allows adding the mandate to the section labeled “other taxes,” hence Mr. Drudge’s chosen name “Liberty tax.”

A Senate Budget Committee aide told Breitbart News, “It is true that thousands of small businesses will be forces to pay Obamacare taxes quarterly in 2014.”

Breitbart reported that Mr. Drudge did respond to the ill-informed critics, tweeting, “Dazed team Obama media reporters think Opt-Out tax ‘year-away’? Not for small businesses that file Qtr estimates. We’re there NOW, baby #pay.”

That tweet was removed from Mr. Drudge’s feed and replaced with another, which linked to the Talking Points Memo. It read: “Obama media team knows they will not get audited for avoiding taxes. I don’t have this luxury. So they mock, ridicule.”