Condon is widely credited as the man who contributed the most to the development of the stab kick, which—once the specially designed "blunter" Sherrin Match II football was introduced into the VFL—became the central feature of Collingwood's pattern of play.

An 18 August 1905 newspaper report, referring to Condon as "that fiery football genius", described his coaching style as a "combination of brimstone oratory and skilful tactics".

He abused field umpire Bill Freame on 7 July 1900 continuously throughout the match against South Melbourne at the Lake Oval after a number of decisions went against the Magpies, and he was suspended for three weeks by the VFL.

[6] After a decision went against the Magpies in the first quarter, Condon abused Crapp throughout the remainder of the match, culminating in his infamous barrage of insults involving the umpire's daughter.

A newspaper report of 17 September 1900 suggested that Condon would now be able to "spend the rest of his days thinking about the joy and glory of his lost future in the game", observed that "Collingwood has turned away from him", and noted that "club discipline has outweighed any sympathy for a fallen hero".

[7] The report provided additional details of the incident: [The third match of the round-robin series against Melbourne was] umpired by an experienced man in H. "Ivo" Crapp.

For more than a century, Condon was the only Collingwood player to have played for ten years across 100-plus games, win a Copeland Trophy and yet not be made a life member.