Etymology
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kingpin (n.)

also king-pin, 1801 as the name of the large pin in the game of kayles (similar to bowls except a club or stick was thrown instead of a ball; see "Games, Gaming and Gamesters' Laws," Frederick Brandt, London, 1871), from king with a sense of "chief" + pin (n.).

The modern use is mainly figurative and is perhaps from the word's use as synonym for king-bolt (itself from 1825), a large, thick, heavy bolt used in a machinery to couple large parts, but if this is the origin, the figurative use is attested earlier (1867) than the literal (1914).

updated on March 15, 2016

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Definitions of kingpin from WordNet

kingpin (n.)
the most important person in a group or undertaking;
Synonyms: top banana / bigwig
kingpin (n.)
bolt that provides a steering joint in a motor vehicle;
Synonyms: kingbolt / swivel pin
kingpin (n.)
the front bowling pin in the triangular arrangement of ten pins;
Synonyms: headpin
Etymologies are not definitions. From wordnet.princeton.edu, not affiliated with etymonline.