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 started his professional basketball career in 2005 playing for Gymnastikos S. Larissas, a team 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.

[3] In January 2010, his contract with Real Madrid was terminated by the club under mutual consent,[4] and in February 2010, Massey signed for Obradoiro CAB, to replace Marc Jackson after his retirement.

[23][24] Massey played internationally for the senior Macedonia national basketball team, after acquiring Macedonian citizenship in 2008.

[25] 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.