Massey was selected 5th overall in the 2005
USBL draft. He started his professional basketball career in 2005 playing for
Gymnastikos S. Larissas, a team in the
Greek League. In the 2005–06 season he was the leading rebounder in the Greek League. This was the main reason why he was acquired by
Aris, one of the top 3 teams in the Greek League, prior to the 2006–07 season. Massey signed a two-year contract extension through the year 2009 with his club Aris in the summer of 2007, but Aris sold him to
Real Madrid in 2008, where he signed a three-year contract. In January 2010, his contract with Real Madrid was terminated by the club under mutual consent, and in February 2010, Massey signed for
Obradoiro CAB, to replace
Marc Jackson after his retirement. On May 14, 2010, he parted ways with Obradoiro. In August 2010, he signed a one-year contract with the Russian team
PBC Lokomotiv-Kuban. On July 28, 2011, he re-signed with Lokomotiv for one more season. He was named to the
All-EuroCup Second Team in 2012. In the summer of 2012, after club decided not to extend his contract, he became a free agent. In November 2012, Massey signed a six-week contract with
Krasnye Krylia of the
PBL. Later, in December 2012, he signed for
Brose Baskets Bamberg of Germany. Massey was suspended for being undisciplined the last few weeks while he was still with Brose Baskets. In early May 2013, he signed with
Champville of Lebanon for the rest of the season. In December 2013, he signed with
Amchit Club for the 2013–14 season. He helped them to make it to the semifinals. In 23 games he averaged 21 points, 8.6 rebounds, 5.5 assists and 2.9 steals per game. After a short stint in Qatar with
Al-Gharafa, on April 22, 2016, he signed in Argentina with
Libertad de Sunchales of the
Liga Nacional de Básquet. On August 10, 2016, Massey signed with Macedonian club
MZT Skopje for the 2016–17 season. On October 10, 2016, he parted ways with MZT after appearing in only three ABA league games. On October 25, 2016, he returned to Libertad de Sunchales for the rest of the season. On October 27, 2017, Massey signed with
Quimsa for the 2017–18 season. ==National team career==