This is less of a TOTI and more like four score and hella years ago on the Interwebs... But there you have it, an emoticon in a news clipping transcribing Abraham Lincoln's 1862 speech.
"A historical newspaper specialist at the digital archival company Proquest believes he has found an example of a sideways winking smiley face embedded in The New York Times transcript of an 1862 speech given by President Lincoln. Other historians are not so sure, saying the semicolon alongside a closed parenthesis is either a mistake or a misinterpretation of something that is perfectly grammatical for that era."
(From my friend Justin)