The name Wiley originated from the Old English word "wil," which means "wilful" or "cunning." It first emerged during the Anglo-Saxon period in Britain, around the 5th to 11th centuries AD. The name was commonly used as a descriptive nickname for someone with a clever or cunning personality.

One of the earliest recorded individuals with the name Wiley was an Anglo-Saxon monk named Wiley of Malmesbury, who lived in the 11th century. He was known for his scholarly works and translations of Latin texts.

In the 13th century, a prominent English knight named Sir Wiley de Charnwood fought in the Barons' War against King John. He was renowned for his strategic military tactics and cunning on the battlefield.

During the Renaissance period, Wiley Tanner was an English playwright and poet who lived from 1550 to 1620. He is best known for his satirical works that often poked fun at the aristocracy and social norms of the time.

In the 18th century, Wiley Jones was an American Revolutionary War soldier who fought alongside George Washington. He was captured by British forces but later escaped and continued his service in the Continental Army.

One of the most famous individuals with the name Wiley is Wiley Post, an American aviator and explorer who lived from 1898 to 1935. He was the first pilot to fly solo around the world, accomplishing the feat in 1933. Post also held several aviation records and worked closely with the famous aviator Amelia Earhart.

Throughout history, the name Wiley has been associated with individuals who possessed intelligence, cunning, and a strategic mindset. While its usage has evolved over time, the name continues to carry a sense of cleverness and wit.