Etymology

pull someone's leg

Today it means: To tease someone; to lead someone on; to goad someone into overreacting. Full definition →

First used late 19th c.
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The story

The phrase from Scotland originally meant to make a fool of someone, often by cheating him. One theory is that it is derived from tripping someone by yanking or pulling his leg in order to make him stumble and look foolish.

First known use, by meaning

  • late 19th c. To extract money from someone (by taking out a loan or by swindling).

Etymology from Wiktionary, CC BY-SA 4.0.