But in 2006, it all fell apart.
During a routine drug test for the Waratahs, he tested positive for cocaine and was banned from the game for two years. And those years away would prove to the toughest challenge of his life. The self-confessed party boy who constantly sought the public spotlight was now forced to do some soul-searching, and most of it wasn't pretty.
But Sailor fought back hard and worked through the shame, throwing himself into charity work and mentoring young people in alcohol and drug awareness programs. With the help of his family and old coach and mentor, Wayne Bennett, he began his path to redemption.
When the ban was up, Sailor made a triumphant return to the code that had first discovered him at age 18, and the St George Illawarra Dragons had a new winger - and a player determined to prove what he was capable of until his final game in 2010. But Crossing the Line isn't just Sailor's story as the comeback king. Written with Jimmy Thomson, Wendell reveals a dark secret that has haunted him since childhood. He tells us what it's like to be a black man in a white man's world and the toll racism takes on elite sport. He shows us how good friends and mentors are so important to our national heroes. And he also demonstrates how crucial the bonds of family - and the love and trust of good people - are for anyone, hero or not.