I've just started re-reading The Phantom Tollbooth, a fantastic tale of wit and wordplay. Every place and person that Milo meets through this story is rich in symbolism, and every piece of description seems carefully chosen. That said, I'm struggling to figure out the Whether Man. Aside from the obvious pun in his name/title, why does he live specifically in the land of Expectations, and why does he talk in an idiosyncratically repetitive way? Surely these connections can't be coincidental.
With the first sound from the horn a little man in a long coat came rushing from the house, speaking as fast as he could and repeating everything several times:
"My, my, my, my, my, welcome, welcome, welcome, welcome to the land of Expectations, to the land of Expectations, to the land of Expectations. We don't get many travelers these days; we certainly don't get many travelers these days. Now what can I do for you? I'm the Whether Man."
"I'm the Whether Man, not the Weather Man, for after all it's more important to know whether there will be weather than what the weather will be." And with that he released a dozen balloons that sailed off into the sky. "Must see which way the wind is blowing," he said, chuckling over his little joke and watching them disappear in all directions.
"What kind of a place is Expectations?" inquired Milo, unable to see the humor and feeling very doubtful of the little man's sanity.
"Good question, good question," he exclaimed. "Expectations is the place you must always go to before you get to where you're going. Of course, some people never go beyond Expectations, but my job is to hurry them along whether they like it or not. Now what else can I do for you?" And before Milo could reply he rushed into the house and reappeared a moment later with a new coat and an umbrella.
"Splendid, splendid, splendid," exclaimed the Whether Man. "Whether or not you find your own way, you're bound to find some way. If you happen to find my way, please return it, as it was lost years ago. I imagine by now it's quite rusty. You did say it was going to rain, didn't you?" And with that he opened the umbrella and walked with Milo to the car.
"I'm glad you made your own decision. I do so hate to make up my mind about anything, whether its good or bad, up or down, in or out, rain or shine. Expect everything, I always say, and the unexpected never happens. Now please drive carefully; good-by, good-by, good-by, good..." His last good-by was drowned out by an enormous clap of thunder, and as Milo drove down the road in the bright sunshine he could see the Whether Man standing in the middle of a fierce cloudburst that seemed to be raining only on him.
The land of Expectations itself has a clear enough symbolic meaning: it's described as fantastically bright and shiny, like people's good expectations of a thing before it happens. The moral in the Whether Man's explanation is that people should go beyond expectations to reach reality.
But what does the Whether Man represent, and why does he live in Expectations? And, whatever he does represent, does it relate symbolically to his repetitive style of speaking (often a character's idiosyncracies somehow reflect whatever it is they correspond to), and to the fact that in the end it rains only on him?