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When I hear that someone or some group have been conniving I think of it as scheming, or secretly planning something.

Looking at the history of the word there has almost always been a sense of “secret” to connive, but in some senses there also seems to have been an unofficial approval of those secret schemes.

The word appeared in English in 1602, 14 years before Shakespeare’s death.  This is one of those words pulled straight from Latin that had never been a French word.

The Latin root meant “to shut the eyes,” so the sense is that officialdom conveniently didn’t see whatever was being secretly planned.

There is even a sense of winking to it so that the planners explicitly knew that their superior knew what they were up to and had unofficially given them the nod.

The con in connive has a meaning of “together,” so that the collaborators can be seen as “winking together.”

The idea that officialdom was “closing its eyes” to some activity actually fits more closely with the word wink than one might imagine given the meaning of wink today.

As I explored in my book Carnal Knowledge although wink means to me and you “to shut one eye voluntarily,” it didn’t originally meant that.  Even though people who are conniving might literally wink at each other, the older meaning of wink – “to close both eyes” – resonates with the authorities looking the other way.

This earlier meaning of closing both eyes still survives for us in the expression to catch forty winks; although wink “to close ones eyes” goes back to Old English before the year 900 and the expression forty winks didn’t show up until the 1800s.

I see that one of the citations in the OED for connive is from Elizabeth Barrett Browning, she of “How do I love thee, let me count the ways” fame.

In this case however her use of connive is in a poem depicting a conversation between the angel Gabriel and Lucifer.

As suspicious as that might sound, this connive is just the opposite; the angel Gabriel is arguing against Lucifer’s depressing stance and saying that

“who despairs, acts; That who acts, connives with God’s relations.”

Since neither Gabriel nor Elizabeth Barrett Browning would think that God would wink at evil behavior, this is a use of connive free of our burden of tricky or covert scheming behavior.

Elizabeth Barrett Browning tells another tale of conniving with God.

Robert Browning wore a full grey beard that Elizabeth thought looked very fetching.  One day he shaved it off and she said that if he didn’t grow it back they were through—I guess beardless wasn’t one of the ways she loved him.

He conceded and the beard grew back, but when it grew back it was no longer grey, it was white.

Elizabeth said this was “the just punishment of the gods.”