When Fred Goldsmith was a kid, his best mate was one of the best footy players he’d ever seen.

Bill Gunn, who lived around the corner from Goldsmith in Williamstown, was a star at football and cricket, both of which the pair played together for most of their lives.

As teenagers, they played footy in the Footscray District Football League, and Goldsmith can still remember when his best friend Billy tied for the Best and Fairest with the great Ted Whitten on a total of 33 votes.

In 1950, Gunn famously told the South Melbourne Football Club secretary that “I’ll sign if my mate signs” - and that mate was Goldsmith.

This weekend marks the 21st anniversary of former South Melbourne captain Gunn's passing, and coincidently it falls on another special day for the Gunn family.

Tomorrow night, Gunn’s grandson Callan Ward, will line up as captain of GWS, taking on his grandfather’s old team at ANZ Stadium.

“It’s Billy Gunn’s anniversary on the weekend - and it’s 21 years since he died,” Goldsmith told sydneyswans.com.au.

“It’s a coincidence that it’s happening this weekend so it’s going to be a big weekend for Callan.

“To see Callan toss the coin this weekend will be lovely.”

Goldsmith, who played 119 games for South Melbourne and is the oldest living Brownlow Medallist, has been closely following Ward’s career.

While Goldsmith is excited about seeing Ward lead GWS in their inaugural game, he said he is most looking forward to seeing Ward wear his grandfather’s number on his back.

“I’ve been watching Callan’s progress over the last few years,” he said.

“I’ve taken a big interest in young Callan and I keep in touch with Callan’s mother Kerry, who is Gunny’s daughter.

“It’s going to be history now that he’s playing his first game with the new Sydney mob and he’s asked especially for his grandfather’s number, number eight.

“Gunny wore number eight and he was captain of the Swans the year I won the Brownlow in 1955.”

Goldsmith said it was clear where Ward got his football talent, saying Gunn was one of the top players he ever took the field with.

“His grandfather was one of the best players that ever played with South Melbourne - he was in the top three,” he said.

“He made the Victorian side after six games on a half forward flank, and then was made All-Australian and played in the 1952 carnival in Brisbane.

“He beat everyone and made the All-Australian team and would have to be the third best player to play for South Melbourne behind Ron Clegg, then Bobby Skilton, then Gunn.

“That’s where Callan gets his football ability from I’d say.”

Ward said he was proud to wear the number eight and follow in the footsteps of his talented grandfather.

"He always wore the number eight and my dad also wore it in the VFA when he was playing for Yarraville and even playing local football at Spotswood," Ward told the Daily Telegraph this week.

"I wore it all the way up from doing Auskick to junior footy at Spotswood and under-18 at the Western Jets."

While Goldsmith would be thrilled to see his mate’s grandson do well this weekend, the former Bloods full back said he would still be barracking hard for the red and white this weekend.

“I’m really looking forward to seeing young Callan running out and wearing number eight, it brings back memories,” he said.

“Of course I’ll be going for Sydney, but I really hope Callan plays a good game.”