Re: Tom suckers his friends into whitewashing the fence for him,.... Perhaps this is where "whitewash" gained its connotation for connivance,..

but i have always heard this kind of conning to be Tomsawyering.. I have been known to engage in it.. and to fall prey to it.. (i've been tomsawyer'd!)

its a classic sort of passive/aggresive action.. (kids do it all the time! )

I think the idea of whitewash (or nowdays, a quick slap of paint) being used to cover up defects, to "give the appearence of new, or clean" is very differented than being tricked into doing someone elses work...

in the worst of the 80's, NY used to board up abandon, burned out building by covering the window openings with sheet metal.. some one had the bright idea of silk screening designs on the sheet metal; curtains, window sill plants, cats, etc. these designer window covered were used where ever a landmark happened be be close to a bad area.. the buildings near the Bronx Zoo was one area.. the idea was to give the illusion the neighborhood was better than it seemed.. a quick glance and you saw 'inhabitated apartments'. reality was burnt out, abandon buildings.. critics at the time refered to the whole project as creating Potamkin villages.