Simon was born in Willemstad, Curaçao. Before signing with the Pirates, Simon signed with the Florida Marlins and New York Yankees in the 2000 season, but did not play in the majors for either franchise. In 2003, Simon was traded by Pittsburgh to the Chicago Cubs, where he had a productive postseason, helping the Cubs to the 2003 National League Championship Series. After the season, Simon was released by Chicago. On February 19, 2004, the Pittsburgh Pirates signed Simon as a free agent to secure the team at first base for the upcoming season. After several months into his second tenure with the Pirates, he was released on August 18, 2004. Simon said, "I'm a fighter," Simon said. "I promise you're going to see me again. You don't have to worry about that." One day after his release from the Pirates, he was acquired by the Tampa BayDevil Rays. After less than a month with Tampa Bay he was released and signed with the Orix Buffaloes of the Japanese Pacific League. Randall represented his country in the 2006 World Baseball Classic for Netherlands along with his fellow country man and old teammate Andruw Jones who he played with the Atlanta Braves. In 2008, Simon played for the independent Newark Bears of the Atlantic League. In 2009, Simon played in the World Baseball Classic on the team representing the Netherlands. The Fargo-Moorhead RedHawks of the Northern League signed Simon to a contract for the 2009 season. Simon played for the Truenos de Tijuana of the Northern Mexican League in the 2011 season, which ended on July 17, 2011.
Sausage race incident
On July 9, 2003, while playing for the Pittsburgh Pirates, during the Milwaukee Brewers' "Sausage Race," in which four contestants wearing sausage costumes have a footrace on the field, Simon leaned over the dugout railing and hit college student Mandy Block with a bat, causing her to fall into the path of another racer. His bat struck only the top padded part of the costume, well above her head position, causing her to lose her balance. Block suffered only a scraped knee. Simon was questioned by police and later fined $432.10 for disorderly conduct. MLB suspended him for 3 games and fined him $2,000. He issued an apology - and an autographed bat - to Block. In addition, later that year, Mandy Block received a complimentary trip to Curaçao, Simon's home island, for two persons from the Curaçao Tourism Board. When he returned to Miller Park later that year as a member of the Chicago Cubs, he purchased Italian Sausages for an entire section, and during the race, his teammates playfully held him back until all the sausages passed the dugout, while manager Dusty Baker guarded the bat rack.It was later said that Simon may have been more fond of the pierogie races at PNC Park,the home of the Pittsburgh Pirates.It was also stated that he may have felt that all of the MLB "mascot" races may have been infringing on the rights of the pierogies,Sauerkraut Saul,Cheese Chester,Jalapeno Hannah and Oliver Onion.
