SOME WORD ORIGINS

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Cobweb:

Cob, or coppe, is the Old English term for spider. It has a cognate word in koppe from Middle Dutch.  Hence cob + web = spider web.

By the way:

The word spider originates from the late 14th c., spydyr which in turn is from Germanic spin-thron (Danish spinder), literally "spinner", the same root as the word spin from the spider’s method of producing silk for its web.

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Stateroom:

Before ships had staterooms, mansions had rooms of state, designed expressly for when royalty or other VIPs dropped by. They were designed and fitted for maximum opulence.

Historically the word “state” has also been used to mean “status” or “rank,” especially if that status is high or powerful. Hence one derivative of this sense was the use of “state,” beginning in the 14th century, to mean “costly or imposing display of dignity, solemnity, pomp and wealth.” The “great dignity and solemnity” part of that sense is reflected in the phrase “to lie in state,” meaning when the body of a celebrated person is ceremoniously displayed before burial.

The “pomp and wealth” sense of this meaning of “state” has given us “stateroom” and “rooms of state.” Aboard ship, the first “staterooms” were the Captain’s quarters, which were grand and luxurious compared to the average sailor’s accommodations. In an aristocratic home, the “rooms of state” were the most expensively decorated, reserved for the most important (and important to impress) guests.

Accordingly the term "state" can be taken more accurately to mean "best". On board a ship, the term state room defines a superior first-class cabin.

 State Rooms, Buckingham Palace

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The whole shebang:

Meaning: the whole lot.

This is an American phrase, from the 1920s.

The earliest known citation of the word “shebang” uses it as some form of hut or rustic dwelling, being from Walt Whitman's Specimen Days, from 1862:

"Besides the hospitals, I also go occasionally on long tours through the camps, talking with the men, &c. Sometimes at night among the groups around the fires, in their shebang enclosures of bushes."

Whitman was referring to a form of rough temporary dwelling, what others might have called a shack or shanty. It may be that shebang, shack and shanty are variants. If so, it is shack and shanty that derived from shebang, as neither of those words are found before the 1860s.

Just a few years after Whitman's poem, the Marysville Tribune, November 1869 printed a list of 'The Idioms of Our New West' and defined 'shebang' as “any sort of house or office." Soon after that, Mark Twain uses 'shebang' in Roughing It, 1872 to refer to a form of vehicle: 

"Take back your money, madam. We can't allow it. You're welcome to ride here as long as you please, but this shebang's chartered, and we can't let you pay a cent."

In June 1872, the same year that Twain was using 'shebang' to mean vehicle, the Sedalia Daily Democrat printed a piece which used the name just to mean 'thing', and this is the earliest example of 'the whole shebang':

"Well, the Democracy can flax [beat up] the whole shebang, and we hope to see our party united."

There are various 'the whole' expressions which derive from America –

'the whole ball of wax'

'the whole nine yards',

'the whole box of dice'

'the whole shooting match'

'the whole enchilada'

'the whole kit and caboodle'.

Some of the above are real objects, some are only expressions to mean the whole thing.

'Shebang' was used the latter way, even if people didn’t (and still don’t) know what a shebang is

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Gerrymander:

Gerrymandering is the manipulation of electoral district boundaries with the intent of creating advantage for a party, group, or class within the constituency.

The term gerrymandering is named after American politician Elbridge Gerry, Vice President of the United States at the time of his death, who, as Governor of Massachusetts in 1812, signed a bill that created a partisan district in the Boston area that was compared to the shape of a mythological salamander.

Elbridge Gerry

Printed in March 1812, this political cartoon was made in reaction to the newly drawn state senate election district of South Essex created by the Massachusetts legislature to favor the Democratic-Republican Party. The caricature satirizes the bizarre shape of the district as a dragon-like "monster", and Federalist newspaper editors and others at the time likened it to a salamander.

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Clue:

A clue is a fact or idea that serves as a guide or aid in a task or problem.

According to Greek mythology, when Theseus entered the Labyrinth to kill the minotaur (a half-man, half-bull), he unraveled a ball of string behind him, so he could find his way back.

In Middle English, such rolled-up yarn was called a clewe. Eventually, clew took on the metaphorical meaning of something that will lead you to a solution. The spelling was changed to clue in the mid-1500s.

Theseus and the Minotaur section of the Archibald Fountain in Hyde Park Sydney

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Assassin:

An assassin is a person who murders an important person for political or religious reasons.

Members of a fanatical Muslim sect during the Crusades used to smoke hashish and then murder leaders on the opposing side. They started going by the name "hashishiyyin," meaning hashish-users in Arabic.

Through centuries of mispronunciation, English arrived at "assassin."

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Whiskey:

Whiskey is a spirit distilled from malted grain, especially barley or rye.

Whiskey is the shortened form of whiskeybae, which comes from the Old English "usquebae," derived from two Gaelic words: uisce (water) and bethu (life). Thus, whiskey literally means "water of life."