Once Hercules slayed the Hydra, he dipped his arrows in the Hydra’s blood. This made his arrows poisonous.

Playing Cards originated in Asia and spread across Europe around the 14th century. It arrived in England a little later than in Spain, Italy and Germany.

“Essentially, the Italian versions of early cards used the suits Cups, Swords, Coins and Batons – which, on migration to England, became Hearts, Spades, Diamonds and Clubs. The image for Spades on English and French cards looks somewhat like that of the German Acorn or Leaf suits, but its origin is revealed by its name rather than its shape. The Spanish and Italian for sword is ‘espada’ and ‘spada’ respectively, hence the suit ‘Swords’ became anglicized as ‘Spades’.”

So where does the non-card-playing meaning come from? It is an Americanism:

First of all, the phrase isn’t found before the 1920s. Damon Runyon, an American journalist and writer, used the expression that way in a piece for Hearst’s International magazine, in October 1929:

“I always hear the same thing about every bum on Broadway, male and female, including some I know are bums, in spades, right from taw.“

Some other spade phrases: “cocky as the King of Spades”, “call a spade a spade”, “spade something up”

“To kick the bucket, to die.”

Although there is not much evidence to support it, one theory as to why the phrase originates from the notion: people hanged themselves by standing on a bucket with a noose around their neck and then kicking the bucket away.

The word Skullduggery has been used to title various things from a 1970s Burt Reynolds film to the University of Adelaide orientation week, established in 1896.  

The origin dates back to 1910 and originally meant “without preparation,” referring to the ease of making a dish of cold turkey. In 1922, the expression acquired its darker connotation related to drug withdrawal.

Example: “That horse is a real daisy.  She’s well worth the price!”

Other etymological sources suggest it derives form the nickname for the Dusenberg, a luxury automobile introduced in the US in the 1920s.

A third possibility is that it come from the nickname given to Italian actress Eleanor Duse, who made headlines as beautiful and talented import to the New York theater world in the 1890s.

The definition has expanded in modern parlance from indicating something or someone superior to also including something that is extraordinary in its negative qualities.

Example:  ”That test was a real doozy.  I sure hope I passed.”

was used to push smoke into a drowning victim in order to warm the victim from the inside-out.

“…A rectal tube inserted into the anus was connected to a fumigator and bellows that forced the smoke into the rectum. The warmth of the smoke was thought to promote respiration, but doubts about the credibility of tobacco enemas led to the popular phrase “blow smoke up one’s ass.” Search on “tobacco smoke enema” for illustrations of the apparatus.”

At the end of the 19th Century, both in Australia and in America, the term was used to denote a weak or effeminate person.

Or, the term could be associated with American tennis player “Gorgeous Gussie” Moran who is best remembered for appearing at Wimbledon in 1949 wearing frilly panties — which caused considerable interest and controversy.

When a Christian deserted and joined the Muslim army, Spanish churchmen labeled a man who denounced his faith a “renegado.” English took this and modified it to ‘renegade’ and was used to designate “the occasional turncoat who denied his religion for profit.”