Massey spent the majority of his playing career with the Castleford Tigers in the Super League after progressing through the club's academy.

Massey played junior rugby league for Wakefield-based side Walton Warriors before being signed to the Castleford Tigers academy at the age of 15.

[14][15] Despite making an impressive debut, he suffered a severe shoulder injury against the Sheffield Eagles in his first game for the club, ending his season prematurely.

[20] In June, the Knights decided against renewing Massey's temporary deal to free up salary cap space and instead develop their own players;[21][22] he scored 2 tries against Rochdale in the Challenge Cup on his return to Castleford.

[31][32] He had originally agreed terms while Featherstone were anticipating promotion to the Super League, but said he "wanted to commit to the project even though we're still in the Championship".

[33] On 4 November 2007, Massey was named as one of ten interchanges for the United States in a 70–0 warm-up game defeat by Cumbria at Barrow's stadium, Craven Park.