Randall Simon's journey through Major League Baseball is marked by his role as a first baseman and designated hitter. Born in Willemstad, Curaçao, Simon began his professional career in the United States after signing with the Atlanta Braves as an amateur free agent. His debut in the major leagues came in 1997 with the Braves, where he played intermittently over the next few seasons.

Simon’s time with the Braves was characterized by limited opportunities, as he was often used as a backup player. In 1999, he was traded to the Florida Marlins, where he continued to serve in a similar capacity. His tenure with the Marlins was short-lived, and he found himself moving to the Detroit Tigers in 2001. It was with the Tigers that Simon began to see more regular playing time, showcasing his abilities as a hitter.

During his stint with the Tigers, Simon demonstrated his potential at the plate. In the 2002 season, he achieved a batting average of .301, hitting 19 home runs and driving in 82 runs. This performance marked the peak of his career, as he became a more integral part of the Tigers' lineup. His ability to hit for average and power made him a valuable asset to the team during this period.

In 2003, Simon was traded to the Pittsburgh Pirates, where he continued to contribute as a solid hitter. However, his time with the Pirates is perhaps best remembered for an off-field incident during a game against the Milwaukee Brewers. Simon playfully hit one of the Brewers' racing sausages with a bat during the popular sausage race, an event that garnered significant media attention and resulted in a fine and suspension.

Later in 2003, Simon was traded to the Chicago Cubs, where he played a role in their postseason run. He provided depth to the Cubs' roster and contributed with timely hitting during their push towards the playoffs. Despite his efforts, the Cubs fell short of reaching the World Series that year.

Following his time with the Cubs, Simon's career saw him move between several teams, including a return to the Pirates and a brief stint with the Tampa Bay Devil Rays. His major league career concluded with the Philadelphia Phillies in 2006. Throughout his time in the majors, Simon was known for his left-handed hitting and his ability to come through in clutch situations.

After leaving Major League Baseball, Simon continued to play professionally in various international leagues, including stints in Japan and Mexico. His career in baseball extended beyond the major leagues, as he sought opportunities to continue playing the game he loved.