Perhaps the best way is that despite spending only 15 years living in Bendigo, on the day of his funeral in June 1952, the city virtually came to a standstill in a sign of respect.

When it comes to football in Bendigo there are no names bigger than that of McCaskill – the man who led Sandhurst to nine premierships between 1926 and 1940 as captain-coach.

Reporting his death in its June 24, 1952, edition, the Bendigo Advertiser described McCaskill as: “recognised as the best football coach in Bendigo’s history and one of the greatest tacticians in Australian Rules.

“McCaskill did much for Bendigo football in the mid-20s when it was languishing and in one season in co-operation with other leading stars of the time lifted the game to such an extent that Bendigo football was considered second only to the VFL in state football circles,” the Bendigo Advertiser wrote.

“A brilliant exponent of the game himself and a clever leader who could impart the finer points of the game and infuse them with enthusiasm, he built Sandhurst into a formidable combination.”

McCaskill’s stunning legacy will once again be relived tonight at the All Seasons Quality Resort when Sandhurst holds its 150th Gala Dinner.

As part of the function, Sandhurst will induct 20 members into its inaugural Hall of Fame.

While the Hall of Fame inductees won’t be revealed until tonight, you can safely assume that when the selection committee first met to discuss the candidates, McCaskill – who played 249 games for the Dragons – was the first name written down.

Here’s why:

In 15 years as Sandhurst’s captain-coach between 1926 and 1940, McCaskill led Sandhurst into 12 grand finals for nine premiership wins and three losses.

Those nine flags included a remarkable six in a row between 1929 and 1934. It’s a BFL record that is unlikely to be ever surpassed.

He also coached premierships in 1927, ’37 and ’40.

The only time the Dragons missed the finals during McCaskill’s reign in charge was in 1939 when Sandhurst finished sixth.

“Bob McCaskill didn’t just influence Sandhurst, it was much broader than that... he came to Bendigo and changed football as we know it,” local football historian Darren Lewis said this week.

“When he came here in 1926 Bendigo football was basically just sides having a kick on a Saturday.

“But he brought a professional approach to fitness and recruiting. He used to drive all over the countryside to recruit players.

“What he did was transform a footy club into a machine. In 15 years at Sandhurst he won nine premierships and was runner-up three times, and the only thing that really stopped them was the war.

“He changed footy in Bendigo and it’s called the McCaskill era for a reason. A big feature of footy at that time was full-forwards kicking 100 goals.

“There were probably more 100-goal forwards in that era than we’ve probably had before or since... it was a very open brand of footy.”

While he was renowned as a master tactician and innovator who was well before his time, it seems McCaskill’s philosophy on the game was also very simple.

In a 1934 newspaper interview under the headline “Old Fox Of Country Football”, when asked for his thoughts on the game, McCaskill answered: “Players don’t always look where they are kicking the ball. Position play is everything. A bit of pace, team work and clever position play will beat any side in the game.”

Later in 1946 in the Sporting Globe Football Book, McCaskill spoke of what would these days be known as his non-negotiables – desire, opportunity, application and experience.

“In sport these things are equally essential. In sport, opportunity generally stimulates the desire, whereas in other matters desire usually finds the opportunity,” he said.

“By desire I mean strength of desire, and in sport that means love of the game strengthened by the determination to succeed.

“Very many elements are necessary in the make-up of a top-line footballer, but these are the three fundamentals: to get the ball, to protect oneself, and to dispose of it constructively.”

After making his coaching name in Bendigo, McCaskill went on to coach VFL clubs North Melbourne and Hawthorn.

He coached North Melbourne in 1941-42, and from 1944-47.

He led North Melbourne into its first finals series in 1945 when the Kangaroos finished fourth, losing to Carlton by 26 points in the first semi-final.

McCaskill’s tenure at North Melbourne came to a controversial end when he was sacked before the 1948 season after earlier being reappointed for a further three years during 1946.

After the Roos finished 10th in 1947, McCaskill was replaced by Wally Cater, with a newspaper article stating: “Several present North officials claim they should not be bound by the decisions of a previous committee.”

McCaskill was later appointed coach of Hawthorn in 1950.

He spent two years coaching the Hawks. Among those he coached was John Kennedy, who would go on to become one of the all-time great VFL-AFL coaches.

“All young players, even now, are very impressed by their first coach at that level, and for me that was Bob McCaskill,” Kennedy, now 83, told the Bendigo Advertiser this week.

“Bob made a big impression on me. He was such an outstanding personality that you just couldn’t help but be affected by his life in general.

“He was way ahead of his time with his ideas on football. ‘Kick it to the open spaces’ he would always say.

“He was always wonderful in his talks to us because he really inspired his players with the way he put things.

“However, the results didn’t give a great image of Bob because we didn’t win a game in his first year at Hawthorn.

“But he had that great ability to have me and my team-mates thinking we were going to win every week. Even after we had lost 17 games and came to play Melbourne in the last match in 1950, he had us convinced we were going to beat Melbourne.

“We didn’t win, but such was his personality, he had us all believing we would.”

Kennedy said that while McCaskill may not have been “universally popular” during his two years at Hawthorn, he was “universally respected”.

“He was a very hard taskmaster. We would have match practice that was sometimes tougher than the games we played,” Kennedy said.

“He had various drills out on the training track where we learned to go in hard and protect ourselves.”

Kennedy played 164 games for Hawthorn and later coached the Hawks to premierships in 1961, ’71 and ’76.

Despite only spending two years playing under McCaskill, the influence of McCaskill carried all through Kennedy’s 412-game coaching career.

And like McCaskill, Kennedy also coached North Melbourne.

“I used to quote Bob a lot because he said a lot of things that stayed in my mind,” Kennedy said.

“I guess it was a combination of what he said, as well as being the person he was.

“He was a very big influence on me, and I can still remember when he died and the funeral was held in Bendigo that the streets were all lined.

“I knew that all the people lining the streets wouldn’t have been pals of his, but they were all respectful of him because he was such a wonderful person.”

Among those Kennedy coached while he was in charge at at Hawthorn was Graham Arthur, who played with Sandhurst before joining the Hawks in 1955.

“When John took over as coach in 1960, he was forever quoting Bob McCaskill,” said Arthur, who is the captain of Hawthorn’s Team of the Century.

While McCaskill died almost 60 years ago to the day, his family name remains strong in Bendigo.

Among the descendants of McCaskill still living in Bendigo is his grandson, Paul McCaskill.

Paul was only two-years-old when McCaskill died, but he has heard no shortage of stories of the legend told by his father and McCaskill’s son, Bob Jnr.

“Dad has told me stories of him being a strong disciplinarian, but had a wonderful personality and could get people to run through brick walls,” Paul said.

“He would train his players extremely hard, but it paid off with their success.

“He was also a great humanitarian.

“There’s a story that he came home one day with a new pair of shoes because he had given his other pair to someone who needed them.

“That’s the sort of person he was. He would give his last cent away if needed.”

While McCaskill – who also served in the Military as a Warrant Officer and Lieutenant – is most well-known for his footballing feats, his other great love was music, in particular the cornet.

In his first season at North Melbourne in 1941, he combined the coaching role with that as the bandmaster of the Royal Park Military Band.

“He used to take bands right throughout Victoria,” said Paul, whose son Sam continued the McCaskill name at Sandhurst, playing with the club during the late ’90s and 2000s.

“He’d go to places like Korong Vale, Charlton and Shepparton. That’s how he earned part of his living, as a bandmaster.

“There was one occasion where he took a band to Sydney and they won the A-grade championship.”

McCaskill was married to Vera and the couple had four children – Bob, Heather, Nancy and Ian, the latter two who are still alive.

McCaskill died on June 23, 1952, aged 56 after a battle with Bright’s disease.

“I have heard the story of when he died, all the shops in Bendigo closed on the day of his funeral,” Paul said.

“That shows the impact he had on Bendigo, even though he was only here for a short time.”

As well as his coaching record, McCaskill played 36 VFL games for Richmond between 1923 and 1925 as a centreman before moving to Bendigo and embarking on the greatest coaching career this city has seen.

However, his memorable career in footy could easily have been over before it had started.

“Just as I was about to give the game up I was persuaded by Dan Minogue to come to town and play with Richmond. I came good and I have carried on since,” McCaskill said in 1941.