No amount of eye-squinting could decipher the details, but if anyone knew exactly what Obama intended to say in his annual address to the nation, it was chief speech writer Keenan.
The 33-year-old Keenan wrote what will be his State of the Union address numero deux after taking over duties last year from Jon Favreau, who left after five years in the job.
A Chicago native who once worked for the late Senator Edward Kennedy of Massachusetts, Keenan joined Obama as an unpaid summer campaign intern in 2007 as Obama sought the Democratic presidential nomination.
At the end of the internship, he returned to Harvard University's John F. Kennedy School of Government to earn a master's degree in public policy, graduating in 2008.
When the White House called, Keenan jumped at the chance to join the administration, according to a 2010 interview he did with the Kennedy School.
Keenan's speechwriting career took off after he crafted the impassioned speech that Obama delivered at a memorial service for victims of a 2011 shooting spree in Tucson, Arizona, where former Representative Gabrielle Giffords was seriously injured.
Keenan, a former high school football player with a hipster-esque beard, also helped write the president's eulogy to Ted Kennedy in 2009.
Obama himself is an accomplished and prolific writer, and Keenan has said it is challenging to meet the president's high standards.
"Our jobs are remarkably like graduate school," Keenan said in the Kennedy School interview. "You get a paper assignment, you might pull an all-nighter or come in really early to finish, and you hand it in and then you get his marks back and find out whether (the President) likes it or not."
At Harvard, Keenan studied speech writing and delivery from public policy professor Steven Jarding.
Jarding described Keenan as passionate and fearless. The classes included mock interviews and presidential debates, drills that did not intimidate Keenan, he said.
"He would come to my office and ask, 'How do I get my foot in the door?'" Jarding told Reuters on Tuesday.
Images of Keenan donning a pirate costume and arm hook while chatting with Obama, and his flirtatious Instagram teases of the State of the Union address reveal a side that his former professor described: "He doesn't take himself seriously, and yet he is a serious person."
When Obama takes the stage Tuesday night, Keenan's skills will also be on trial, Jarding said.
"Even in a room (full of) exceptional students, I knew that this is somebody that we should watch, and that is something that we're going to see unfold tonight," Jarding said.
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