Taken on at Tottenham as a youngster, Michael Kightly dropped out of the club's academy to go back to playing at a lower level, before making his way up through the leagues.
Kightly left the Spurs Academy at the age of 14 and went to play for his local team, Basildon Town, where he was in the first team at the age of 15. Spotted by local Football League club Southend United, he was offered a professional contract at 17, but found that he was not a regular in the team under Steve Tilson, so turned to non-league Grays Athletic to play his football.
Under Andy King, he starred for the club as they pushed up the Vauxhall Conference and when Wolverhampton Wanderers took him on loan, he decided to stay with them on a permanent basis rather than take up the offer of a move to Manchester United, with Alex Ferguson making a personal phone call to the Essex club about his availability.
With Wolves, he played consistently well and earned a call-up to the England Under-21 side in November 2008, which was a result of helping his club side up the Championship and towards the Premier League.
Ironically, during his time at both Grays and Wolverhampton, he was linked with an interest from Tottenham.