Career
Standing at 6 ft 7 ½ in (202 m), he plays at the power forward position. He then transferred to play college basketball at Kansas State University, where he earned the Big 12 Conference newcomer of the year honor in 2004. He was named to the 3rd and 2nd All Big 12 teams in 2004 and 2005 respectively.
He was selected 5th overall in the 2005 USBL draft.
He started his professional basketball career in 2005 playing for Gymnastikos South. Larissas, a team in the Greek League. In the 2005-2006 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 2006-2007 season. He was declared the most spectacular basketball player of the Euroleague 2006-2007 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 Civil Aeronautics Board, 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 2013-2014 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.
In November 2014, he signed with Sporting First Rate (at Lloyd's) Riyadi Beirut.
Massey played internationally for the Macedonian national basketball team, after acquiring Macedonian citizenship in 2008. He has played for Macedonia in the EuroBasket 2009 qualification in September 2008, helping the team to reach the final tournament for the first time since 1999.