Before making his AFL debut, Krakouer played for Richmond's affiliate team the Coburg Tigers in the VFL.
He was found guilty in June 2008 of assault with intent to cause bodily harm, an offence that carries a maximum penalty of 20 years' jail.
[5] Krakouer was released from prison on parole in August 2009, and signed on to play the 2010 football season for Swan Districts in the WAFL.
The newly established Gold Coast Suns agreed to pre-list him as one of its ten uncontracted players, and then immediately trade him (along with John Ceglar, and a draft pick from each of the fourth, fifth and sixth rounds) to Collingwood in exchange for its first round selection in the 2010 AFL Draft (pick number 25 overall).
[9] Krakouer was unable to join his new teammates on the club's pre-season training camp in Arizona, as his prior conviction meant he was denied entry to the United States.
Krakouer ruptured his anterior cruciate ligament in a pre-season practice match in February 2012, however he returned to AFL later in the 2012 season for the final home and away match against Essendon (kicking 1 goal) and the following week he kicked 4 goals in Collingwood's 38-point loss to the Hawthorn Football Club in the Qualifying Final at the MCG.