Ossie grew up in Skem and joined the Everton Youth Academy where he was part of the victorious 1998 FA Youth Cup winning side.
He was loaned to Carlisle United in October 2002 where he was a big success being voted Player of the Year. In 2003 he was loaned to Derby County where he helped them avoid relegation, Derby tried to sign Leon.
He got his first chance for Everton away at Wolves in 2004 where he scored after just 3 minutes, he went on to become a first team regular usually playing wide midfield in 2004.
Ossie has his detractors but is Everton through and through and whilst small in stature he has a big blue heart.