1. In 1792, Kentucky became the 15th state to join the Union. The name "Kentucky" comes from a Native American word meaning "meadow" or "the dark and bloody ground."

2. On December 14, 1825, the Ashland estate in Lexington was purchased by Henry Clay, a lawyer, statesman, and prominent Kentucky figure. The estate now serves as a museum and national historic landmark.

3. In 1937, the Harlan County War culminated in the "Bloody Harlan" conflict on December 14. The violence resulted from a labor strike among coal miners and their families against mining companies, which led to a declaration of martial law in the county.

4. On December 14, 1941, the United States declared war on Germany and officially entered World War II. Many Kentuckians served in the armed forces during the war, including the famous Tuskegee Airmen, a group of African American pilots trained at Tuskegee Institute in Alabama.

5. The Kentucky Wildcats men's basketball team won their 2000th game in program history on December 14, 2019, with a victory over the Georgia Tech Yellow Jackets. The Wildcats have won multiple national championships and produced numerous NBA players over the years.