Nailon was a graduate of South Bend Clay High School where, along with sophomore and former Purdue player, Jaraan Cornell, the two led the Colonials to capture the 1994 Indiana State Championship title, scoring a combined 46 points.

He has played for the Hornets (in separate stints for both Charlotte and New Orleans franchises in 2000 to 2002 and 2004–05 respectively), the New York Knicks (2002–03), Atlanta Hawks (2003–04), Orlando Magic (2003–04), Cleveland Cavaliers (2003–04) and Philadelphia 76ers (2005–06).

Nailon feuded with coach Paul Silas while at Charlotte over minutes played which led to him being released and leaving for the Knicks.

[1] Nailon was recommended to play for the Knicks in a phone call then coach Don Chaney made to Silas.

His international experience includes playing for Adecco Milano in Italy (1999-00), Bnei HaSharon in Israel (2006–07; 2010–11), Lokomotiv Novosibirsk in Russia (2007–08), Al-Riyadi in Lebanon, Leones de Ponce (2009) and Piratas de Quebradillas in Puerto Rico (2010).