Gruenebaum, nicknamed "the Hebrew Hammer," played college soccer at University of Kentucky from 2001 to 2005, and was also was part of the 2005 Des Moines Menace USL Premier Development League Championship team. He also led the Menace to the fourth round of the US Open Cup. There, he played against his hometown Major League Soccer side Wizards.
He was drafted in the first round, 3rd overall, by the Columbus Crew in the 2006 MLS Supplemental Draft.