Holland is an AFL Rising Star Award winner, a best and fairest and leading goal kicker at Hawthorn and represented Australia in International Rules.
Originally from South Australian National Football League (SANFL) club North Adelaide, Holland was recruited by Hawthorn at the 1992 AFL Draft.
Holland was Hawthorn's leading goalkicker in 1997 and 2000, when he also won the club best and fairest award in a tie with Daniel Chick.
[2] At the end of 2001, Holland signed a contract, worth millions of dollars, to play for Hawthorn for four more years.
He began working for the Labor Party lawyers, Holding Redlich followed by the Australian Sports Commission in Canberra.