A hard-hitting infielder, Raymond signed with the Cleveland Indians in 1984. He played minor league baseball in Batavia, New York and Waterloo, Iowa. Howard has coach high school baseball for 24 years, and is presently the head baseball coach at Francis Howell Central High. Four of his teams have made it to the finals in the Missouri State Tournament.

In 2011, Howard was named Coach of the year by GSLAU. He has worked at baseball camps around Missouri for over 24 years and has been a little league coach for 14 years. Ray also played for the St. Louis Union Printers.