Gruenebaum, who is Jewish, is an Overland Park, Kansas, native.[1] He was an All-American at Blue Valley North High School. He attended the University of Kentucky, where he recorded 21 shutouts in 66 collegiate games. Gruenebaum earned All-Conference honors and picked up the nickname "The Hebrew Hammer."[2]
Gruenebaum was selected by the Columbus Crew with the third overall pick in the 2006 MLS Supplemental Draft. He made his MLS debut in May 2006 when Jon Busch suffered a knee injury in a match against D.C. United and started the final two matches of the season.
He started ten matches in the 2007 season, earning his first two career shutouts in back-to-back matches in April. However, his playing time gradually decreased as Will Hesmer established himself as the starting goalkeeper. He made just one league start in 2008 as the Crew won the Supporters' Shield and MLS Cup.[4]
Playing time remained sporadic due to the presence of Hesmer and Gruenebaum's own injuries, but he finally enjoyed a breakout season in 2012, starting 33 matches (including eight shutouts) as Hesmer missed time with injuries. He continued to start in 2013 despite missing time due to injuries.
Following the 2013 season, Gruenenbaum was traded to his hometown club, Sporting Kansas City, in exchange for a second-round pick in the 2016 MLS SuperDraft.[3] After one season in Kansas City, Gruenenbaum's 2015 contract option was declined and he entered the 2014 MLS Re-Entry Draft. He was selected in stage one of the draft by San Jose Earthquakes.[5] However, Gruenenbaum instead opted to retire and take a role as a broadcaster with Sporting.[6]