Today, we know the word refers to 'a person who acts obsequiously towards someone important in order to gain advantage.' But that's not its original meaning.
Sycophant comes from the Greek sykophantes. It means “slanderer,” but a literal translation of the word’s roots (sykon and phainein) is “the one who shows the figs.”
In 6th century Athens, it was illegal to export foods other than olives from the territory. This made goods like figs contraband that smugglers would sneak out of the territory for extra profit. Sometimes, snitches would sell out these smugglers to the authorities, and they would be reputed as “one who showed the figs.” Basically, they were known as a narc on those ancient Greek streets.
“If it was part of his purpose to ingratiate himself with the authorities, he was close to being a sycophant in the modern sense of the word,” Robin Waterfield writes in his book Why Socrates Died.
But this account is not considered substantiated by the Oxford English Dictionary. It provides an alternative history in which “showing the figs” was a vulgar gesture made by sticking the thumb between two fingers. In ancient Greece, the fig was symbolic of a vagina, and when you stick the thumb between - well, you see where this is going.
According the OED, politicians would publicly scorn this uncouth gesture while privately encouraging their followers to taunt their opponents with it. The toadies who did so to endear themselves to these two-faced politicians were belittled as one who shows the figs - effectively, a brown noser.
Whichever history is true, it’s interesting - and a little disheartening - to see that while the words may have changed, the political realities remain steadfast.