He was rated by Jack Dyer as better than Haydn Bunton, Sr and equal to Dick Reynolds, making him one of the best players in the history of the game.
In September 2023 Skilton was elevated to Legend status in the Sport Australia Hall of Fame, only the 4th AFL player to achieve the honour.
It was his appearance on the front page of The Sun News-Pictorial in 1968 with two black eyes that earned him the Douglas Wilkie Medal.
The black eyes were a consequence of a severe facial injury, which included depressed fractures of his cheekbones, due to collisions in successive weeks from Footscray's Ken Greenwood, his own teammate John Rantall and Len Thompson.
He missed the entire 1969 VFL season after snapping an achilles tendon in a pre-season practice match against SANFL club Port Adelaide.
He often said that he would trade any of his three Brownlow Medals for a premiership or even the chance to play in a Grand Final, and felt the highest point of his career was the one occasion South Melbourne made the finals in 1970 (under the great Norm Smith), finishing fourth after losing the first semi-final against St Kilda.