from http://www.word-detective.com/060704.html#pillartopost Dear Word Detective: I've been thoroughly perusing your archives after stumbling upon your wonderful site some weeks ago. I could not however seem to locate the origins of the phrase "from pillar to post." I would be very appreciative if you would be so kind as to enlighten this tortured soul. I fear I've looked everywhere with no satisfaction. -- Chris. Good question, and your narrative of frustration reminds me of the awesome responsibility I bear to mouse potatoes everywhere. Ordinarily, on a day like today, I would skip gaily from my door, eager to mow our four acres of lawn and then, perhaps, whistle a cheerful tune as I prune a few hundred useless shrubs. But as long as one reader is tormented by a mysterious phrase, I cannot shirk my etymological duty. Gosh darn, I do love mowing. Well, maybe next year. I must note, however, that in your question you inexplicably missed a golden opportunity to say that you yourself have been "from pillar to post" in search of an answer to your question. "To go (or run, hunt, etc.) from pillar to post" means to travel (whether literally or figuratively) from one place, person or resource to another in search of something," usually with much frustration and little or no success. There are two theories about the origin of "from pillar to post," which first appeared way back in the 15th century, oddly enough in the reversed form "post to pillar." The most popular theory traces the phrase to the sport of "real tennis" (called "court tennis" in the U.S.), an early version of the game played indoors. This explanation posits that a tennis player chasing the ball ricocheting off the posts and pillars of the indoor court served as a vivid metaphor for someone traveling hither and yon in search of something. The other theory interprets "post" as a whipping post and "pillar" as originally being "pillory," a punishment-through-humiliation contraption consisting of a short post topped with a wooden frame through which an offender's head and hands are locked so that he or she might be mocked by passers-by and occasional pigeons. If this theory is correct, the original order of "from post to pillar" would make more sense, as the logical progression of 15th century public punishment would probably be whipping first, then confinement in pillory. Whichever theory is correct (and I lean toward the "pillory" one myself), modern bureaucracy (as well as that great rummage sale of knowledge, the internet) have made it only more likely that we'll spend lots and lots of time running from pillar to post. -- I hope this answers your question.

Pillar to Post is an ancient phrase going back to at least the 15th century. It originated in aristocratic circles. It may have come from the medieval punishment of the “pillar” and whipping post. In the old days, criminals were first tied to a "post" in the marketplace and whipped. After that they were dragged to a pillory ("pillar"). This was essentially a wooden frame that had three holes in it. The prisoner was made to put his head and his two hands through the holes, and made to stand or kneel for days. The public had fun throwing rotten vegetables and eggs at the hapless victim. Another meaning of Pillar to Post From one thing or place to another, hither and thither. For example, After Kevin joined the Air Force, the family kept moving from pillar to post. This expression began life in the early 1400s as from post to pillar, an order no longer used. According to some scholars, the expression comes from the world of court tennis, a game that I understand is very different from the game of lawn tennis that is played today. In the UK and the Commonwealth of Nations, a pillar-box is a freestanding box where post is deposited to be collected by the Royal Mail and forwarded to the addressee. Pillar-boxes have been in use since 1855, only 15 years after the introduction of the first penny post. Standard British pillar-boxes are painted red since 1874. Pillar to post in this sense has a different meaning. From pillar to post - having to go to lots of places, probably unwillingly or unnecessarily - from the metaphor of a riding school, when horses were ridden in and around a ring, which contained a central pillar, and surrounding posts in pairs. From various net sources.

From "Brewer's Dictionary of Phrase and Fable"... From pillar to post. Hither and thither; from one thing to another without definite purpose; harassed and badgered. The phrase was originally "from post to pillar", and comes from the old tennis-courts in allusion to the banging about of the balls.