1: to warn a person about something after it is far too late for them to do anything about it
2: to attempt (generally poorly and without success) to cover up something (often done at the time of the commission of the act which is to be covered up or immediately after)
Etymology: "Kick the Pillow" is derived from a practice of Feudal Japan. It was considered dishonorable to kill a sleeping enemy, so a warrior would kick his enemy's pillow in order to wake him just before chopping off his head. This allowed the warrior to maintain his honor (at least by the literal letter of the rules) while preserving the advantage of taking an enemy completely unawares.
1: (Historical) The Japanese sent a telegram to their embassy in Washington D.C warning of their impending attack on Pearl Harbor, which was intended to be delivered to the US Government just minutes before their attack began. Unfortunately the ambassador was too slow in decrypting the message, and the US had already decalred war on Japan before he finished, so it was never delivered.
2: "I'm back. Gotta love taking long lunch breaks."
"Yeah, well the boss wants to see you in his office. Last week I heard him saying he was thinking about firing you for taking extended lunch breaks."
"Oh, fantastic! Thanks for kicking the pillow, jerk!"
3: "Surprise! My mother is moving in with us! She just pulled into the driveway."
"Thanks for kicking the pillow, honey."
(Guess who's not getting laid until she moves out?)
4: "You slept with her?!"
"Well... I did say I wanted to talk about seeing other people."
"Oh yeah, good job kicking the pillow."
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