Born in Fort Meade, Florida, Andrew Stefan McCutchen was a star athlete for the Fort Meade High School baseball, football and track teams. Back in 2005, Baseball America offered this scouting report for McCutchen heading into the MLB Draft: "McCutchen has quick hands and a compact swing, producing surprising raw power for his size and giving him the bat speed to lash line drives to all fields. His athletic ability, speed and frame earn comparisons to Mets prospect Lastings Milledge, but he's more polished at the plate, earning 60 and 70 grades from scouts (on the 20-80 scouting scale) with 50 raw power.