Herbie Matthews

The son of legendary South Melbourne Brownlow Medallist Herb Matthews, Herbie Matthews faced a delayed start to his family destiny due to the era's rigid residential zoning laws, which initially bound him to Melbourne. After debuting for the Demons as a teenager in 1961 and managing 20 appearances, he secured a mid-season clearance to South Melbourne in 1964, finally allowing him to don the famous red and white chevron at the Lakeside Oval.

Matthews settled into the Swans' lineup primarily as a wingman, offering consistent service over five and a half seasons at his father's old club. While he did not emulate the superstar status of his parent, he carved out a respectable VFL tenure that saw him surpass the 100-game milestone across his two clubs. His career notably cemented a rare three-generation dynasty, serving as the bridge between his father and his own son, Ben Matthews, who would later become a premiership player for the relocated Sydney Swans.