Condon was a highly skilled player, a wiry and tenacious man of greater thanaverage height, with great speed, brilliant evasive skills, and an outstanding capacity for reading a game. He played mainly as a "follower". He is widely credited as the man who contributed the most to the development of the stab-kick which became the central feature of the Collingwood football team's pattern of play. An 18 August 1905 newspaper report, referring to him as "that fiery football genius Dick Condon", described his coaching style as a "combination of brimstone oratory and skilful tactics".
Physical skills
In physical terms he was an extremely flexible and well-balanced player. He was able to pick the ball up from the ground with either hand, he was able to kick place-kicks, punt-kicks, drop-kicks, and stab-kicks with either foot, and he could handball with either hand.
Abrasive nature
He was far from well-balanced in terms of his threshold for violence, his short temper with club officials and umpires, his view that things must always be seen from his own perspective, his intolerance of failure, and his propensity for continuously abusing umpires, all of which were continuously displayed throughout his long career.
Lifetime suspension
Halfway through the 1900 season, Condon was appointed captain of Collingwood. In his new role as captain, he gave the umpires an even harder time. 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. Two weeks later, whilst still under VFL suspension, he got into a fist-fight with teammate Arthur Robson in the middle of Collingwood's three-quarter time huddle; the pair had to be restrained by the umpires, teammates and Collingwood club officials. On 1 September 1900, during Collingwood's second round-robin finals match against Geelong at the Corio Oval, Condon became so upset with the umpiring of Dick Gibson during the last quarter of the match that he lost his temper and signalled for his teammates to follow him off the Corio Oval, demanding that the Collingwood match committee order the Collingwood players from the field. After umpire Gibson threatened to report the entire Collingwood team for bringing the game into disrepute, the Collingwood committee refused to do so, and instead ordered Condon and the team to either return to the field, or be expelled from the club. At that stage Collingwood was a point ahead of Geelong, but Condon's behaviour so unsettled his team that it did not score again, and lost to Geelong 6.8 to 4.7. It was the loss in this match that eliminated Collingwood from premiership calculations in that year. In the final match of the three round-robin match series the following week, Collingwood played against Melbourne Football Club at the Lake Oval. The field umpire for the match, Henry "Ivo" Crapp, was considered to be the most experienced umpire in the competition. 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. He was reported for his conduct, and the VFL Investigative Committee immediately suspended Condon for life. 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", provided additional details of the incident:
Appeal and reinstatement
Over an eighteen-month period, Condon appealed against his lifetime ban on three occasions. His last appeal was successful, and, having not played a single game in 1901, he played his first return game for Collingwood against Melbourne at the Melbourne Cricket Ground on 19 May 1902.
Senior football career
1894-1896, 1897-1900, 1902-1906: 194 games, 115 goals for Collingwood.
1899-1900: Was intermittently captain of Collingwood.
1905-1906: Captain-Coach of Collingwood
*His abrasive character caused so much discontent at Collingwood that he was asked to leave at the end of 1906.
1907: Spent season in Tasmania as a field umpire.
1908-1909: 32 games, 26 goals for Richmond.
1908-1909: Coach of Richmond in its first two years in the VFL competition.
*His abrasive character caused so much discontent at Richmond that he was asked to leave at the end of 1909.
He was the only Collingwood ten years/100 games played/Copeland Trophy winner not to be made a life member until the 2013 Collingwood Annual General Meeting, 107 years after his last match for Collingwood and 67 years after his death. The award was accepted by his great-nephew, Bob Condon, on behalf of the Condon family.