"Pajama Boy" is a derisive term for a photograph posted online in 2013 by the American political organization Organizing for Action (OFA) of one of its employees, Ethan Krupp, in support of the Patient Protection and Affordable Care Act, otherwise known as Obamacare.
The photo was posted on December 17, 2013 by the organization, which advocated for the legislative agenda of President Barack Obama, from President Obama's own Twitter account. It was part of a general campaign to get younger Americans to sign up for the health insurance program. The photo showed Krupp wearing thick-rimmed glasses, wearing black-and-red plaid onesie pajamas, and cradling a mug. The accompanying text read: "Wear pajamas. Drink hot chocolate. Talk about getting health insurance. #GetTalking." The tweet linked to the OFA website, which encouraged individuals to discuss Obamacare during the holiday season with those family members that are uninsured, and encourage them to sign up.
Pajama Boy soon developed into an Internet meme in which the Pajama Boy image was digitally inserted into other photos, or the text of the tweet was revised or new text added to mock the campaign.
The week after the photo's debut, Washington Post reporter Chris Cillizza opined in his "Worst Week in Washington" column that "Pajama Boy was the latest swing and miss in efforts by Obama allies".
The day after the original tweet, December 18, New Jersey Republican Governor Chris Christie lampooned and criticized Pajama Boy with his own tweet, which featured a photo of him volunteering in an apron with the accompanying text: "Get out of your pajamas. Put on an apron. Get volunteering. #SeasonOfService."
Libertarian commentator Nick Gillespie, writing in the Reason magazine blog, wrote that "for many - arguably most - Americans, this guy is hipster douchitude on a cracker," the image succeeded in getting "people to talk about health insurance".
Writing in Forward, Jay Michaelson suggested that criticism of Pajama Boy was driven by unconscious feelings of Anti-Semitism, declaring that, though there was no overt mention of Pajama Boy's religion or ethnicity, "Pajama Boy is a member of the tribe. Look at him. Pale Ashkenazic skin, Jew-fro’d black curls, Woody Allen specs. Even the smart-ass expression on his face screams of the Wise Son from the Passover Seder".
In Bloomberg News, libertarian pundit Megan McArdle said conservatives got "trolled" by Pajama Boy: "The purpose of Pajama Boy is not to get people to buy health insurance, but to get a rise out of conservatives -- and thereby to engage the solidaristic, money-raising, meme-spreading power of OFA’s liberal base." Analyzing the perceived issues with the campaign, however, Salon wrote that "Organizing for America has a tendency to try to promote Obamacare on Twitter with images that, one imagines, they think will be potentially viral. But what tends to happen instead is that OFA’s tweets are ignored by basically everyone — except for conservative tweeters."
- Spiering, Charlie (19 December 2013). "Meet Ethan Krupp: Pajamacare boy and Organizing for Action employee". Washington Examiner. Retrieved 18 December 2016.
- "How do you plan to spend the cold days of December?". Twitter. Organizing for Action. 17 December 2013.
- "Health Care for the Holidays". Organizing for Action. 2013. Archived from the original on 28 November 2013. Retrieved 18 December 2016.
- Cillizza, Chris (20 December 2013). "Who had the worst week in Washington? Pajama Boy.". The Washington Post. Retrieved 18 December 2016.
- Blake, Aaron (18 December 2013). "Christie tweets retort to Obama's 'Pajama Boy'". The Washington Post. Retrieved 18 December 2016.
- "NRO Slideshows: Pajama Boy". National Review. 18 December 2013. Archived from the original on 22 December 2013. Retrieved 18 December 2016.
- Lowry, Rich (18 December 2013). "Pajama Boy, An Insufferable Man-Child". Politico. Retrieved 18 December 2016.
- Cilliza, Chris (20 December 2013). "Who had the worst week in Washington? Pajama Boy". Washington Post. Retrieved 20 June 2017.
- "In New Jersey, we are spending the cold days of December volunteering". Twitter. Governor Christie. 18 December 2013.
- "Chris Christie dresses down Pajama Boy". Politico. 18 December 2013.
- Gillespie, Nick (December 18, 2013). "If You Think the Godawful "Pajama Boy" Obamacare Ad is Godawful, You're Probably Not Its Audience.". Reason Magazine Hit & Run Blog.
- Michaelson, Jay (28 December 2013). "Obamacare 'Pajama Boy' Controversy Wrapped in Anti-Semitism Read". Forward. Retrieved 20 June 2017.
- McArdle, Megan (19 December 2013). "Conservatives Are Getting Trolled by Pajama Boy". Bloomberg News.
- Isquith, Elias (18 December 2013). "Conservative Twitter hate-loves Organizing for Action’s new Obamacare meme". Salon. Retrieved 20 June 2017.