1. In 1857, the first Kentucky Derby was held in Louisville, starting the now world-famous horse racing event. Initially, the Derby was run on May 17th but in 1932 it was permanently moved to the first Saturday in May.

2. On May 23, 1861, Kentucky declared its neutrality during the Civil War. Despite this declaration, both the Union and Confederacy forcibly recruited soldiers from Kentucky and the state became a crucial battleground during the war.

3. In 1922, Henry Clay Frick II laid the cornerstone for the Frick Art Museum in Pittsburgh, Pennsylvania. Frick was born in West Overton, Kentucky in 1879 and was the grandson of industrialist Henry Clay Frick.

4. Musician Rosemary Clooney, born in Maysville, Kentucky in 1928, performed at a concert in Las Vegas on May 23, 1960, with the Rat Pack. She would go on to have a successful career as a jazz and pop singer, with hits like "Come On-a My House" and "Mambo Italiano."

5. On May 23, 2019, Kentucky Governor Matt Bevin announced that General Electric (GE) would no longer manufacture industrial engines at their plant in Ashland, Kentucky, resulting in the loss of 235 jobs. The plant had been in operation for over 100 years and produced engines for various industries, including marine, oil and gas, and power generation.