Herbie Kent’s career as the VFL’s most prolific boundary umpire began at the Lake Oval on 3 May 1941. During the next four seasons he combined his umpiring with a serious athletic career and war work. It was at the end of the 1944 season that he experienced finals action for the first time when he was appointed to the Second- Semi Final. The following year he was in the finals again and ran the Preliminary Final which many claim was more of a bloodbath than the following weeks 1945 Grand Final. There were open brawls, with liberal use of the fist and boots, and, in a screaming finish Carlton kicked seven goals three in nineteen minutes to steal victory from five goals behind. It was a violent time in football and Kent was one of the umpiring who had to be protected by police with batons as they left Princes Park following an unlikely North Melbourne victory in 1948. Consistent performances and finals in five of the next six seasons took Kent’s tally of VFL matches to 170 but his 171st was to be a watershed as he finally broke through with his first Grand Final. In 1952 Geelong took it’s second successive flag and Herb was on the boundary.
In 1956 Kent was appointed to Grand Final number two – Melbourne v. Collingwood – and three seasons later his third, another Demon victory, this time over Essendon. Successful in home and away, finals and also in interstate fixtures (four) Kent became the first boundary umpire to officiate in 300 when he took the field late in 1961. He would cap that year with this fourth and last Grand Final. Herbert Kent retired from the VFL at the end of the 1963, 23 seasons and 330 matches after he began. He became a life member of the VFLUA in 1954, and was a nominee for the AFLUA Team of the Century.