One of Orillia, Ontario’s notable teams is the 1914-15 Orillia intermediate hockey team, which captured the intermediate crown and, with it, the John Ross Robertson Trophy.

In the article, “Famed 1914-15 hockey team’s experiences during First World War part of Doors Open Orillia”, Orillia Packet and Times, the article mentions the players on that 1914-15 team, some of which would be players on the famous 40th Battery of the Royal Canadian Artillery hockey team:

The team consisted of Ted Corbould and Norm Cooke in goal, defencemen Norman Harvie, Ken MacNab and Morley Carter. Lovering Jupp was the rover, centres were George Ross and Andy Tudhope, while Vic Draper and Gordon MacDonald were on the wings. They put Orillia on the map, with some of the players being recognized as the best in the game.

“Speedy” Jupp was revered as possibly the best rover in Canada. The First World War had begun in 1914, and their win gave Orillia something to celebrate amid the stories of horror emerging from the battlefields of Europe.

The team was ready to build a hockey dynasty, but it was not to be. The Great War was not going to be over in a few months, as many had hoped. Hockey players from all over Canada were signing up. So it was for Orillia’s championship team, its hockey hopes and dreams interrupted by the First World War.

The athletes enlisted in September 1915, with some of the boys becoming players on the 40th Battery Artillery’s hockey team. The leader of this team and an officer of the battery was hockey legend Conn Smythe.

He is best known as the principal owner of the Toronto Maple Leafs from 1927 to 1961 and was behind the building of Maple Leaf Gardens.

Fifteen years after Smythe’s Maple Leafs won the Stanley Cup, he said, “Of all the forwards that had ever been my good fortune to have play on my team, Orillia’s Love Jupp was the greatest.” He also remarked Jupp would have made his Leafs’ first line that Stanley Cup season.

While in basic training, the 40th Battery hockey team entered the Ontario Hockey Association senior league and was well on its way to capturing the senior championship when the unit was ordered overseas to fight in the trenches.

Conn Smythe was at university in Toronto studying and playing hockey for the university varsity hockey team, winning the Ontario championship.

A week after winning the OHA championship in March 1915, Smythe and his eight teammates enlisted. Smythe recalled in his memoirs that he and several classmates tried to enlist at the beginning of the 1914–15 season, but were told to come back when they had beards. After securing a provisional rank of lieutenant with the 2nd (Ottawa) Battery, 8th Brigade, on July 17, he headed to the Royal School of Artillery in Kingston, Ontario, in August for five weeks of training. He made full lieutenant on September 11, and was able to get himself transferred to the 40th (Sportsmen’s) Battery of Hamilton, organized by publishing figure Gordon Southam, son of William Southam. (Source: Military Wiki)

University hockey players were especially keen. Four days after the University of Toronto’s varsity hockey team won the Ontario Junior Championship, and in the spirit of a ‘pals’ battalion’, the entire team enlisted.[50] Captain Conn Smythe of the varsity hockey team became Gunner Conn Smythe of the 25th Battalion of the Canadian Field Artillery.[51] For Smythe, there was a sense of urgency of playing a part in the ‘big game’ that was the Great War: ‘Somebody asked me once whether soldiers talked much about fear of being wounded or killed. I never heard that during the First World War. It was always fear that we wouldn’t get there.’ [52] In February of the following year, Gordon Southam organized a sportsmen’s battery to serve in the CEF.[53] Southam, who was later killed at the front, asked Smythe to organize the battery’s hockey team. By now a member of the 40th Battery of the Royal Canadian Artillery, Lieutenant Smythe led a military team that happened to include ten of Ontario’s finest hockey players.[54]

Source: Skating to Armageddon: Canada, Hockey and the First World War JJ Wilson

The Ontario Hockey Association was in a tough situation with the World War taking player’s from member teams, the quality of hockey being diminished, and revenues impacted.

The unit, with Smythe as team manager, organized a team to compete in the Ontario Hockey Association’s senior league; they were one of four Toronto-based teams in the league in 1916. He played one game at centre, and then decided to replace himself with a better player. The team did not complete the season, as the 40th Battery went overseas in February 1916.

The Ontario Hockey Association (OHA) found it increasingly difficult to continue operations during the First World War when players enlisted in the CEF and were taken overseas. However, the OHA soon realized the benefits of including in their league teams comprised of soldiers not yet called to Europe. Conn Smythe’s 40th Battery competed in the Toronto division of the OHA and the soldier team was loved by ‘patriotic Toronto’.[55]

According to J.J. Wilson:

The 40th Battery did eventually head overseas and saw action on the Somme in the fall of 1916. Over 24,000 Canadians were killed at the Somme in the space of five months. Every senior officer in Smythe’s battery was either killed or badly wounded. For Smythe, however, the biggest fear was being called ‘yellow’ –as he remembered, ‘I couldn’t have stood that. The two qualities I admire most are guts and loyalty.’ [56] In Smythe’s mind hockey had given him the ‘guts’ to persevere in dire circumstances: ‘There was some argument that maybe we’d get lost. I wasn’t worried about that. My men, Hamilton and Orillia fellows, were used to playing hockey. … I knew what I was going to do.’ [57] In February of 1917, Smythe charged a German trench with a revolver, shot a couple of Germans and brought two prisoners back to the Canadian lines. He was awarded the Military Cross. In the spring of 1917, Smythe joined the Royal Flying Corps (RFC) as an ‘Artillery Observer’, and on 14 October, he became a prisoner of war when his plane crashed into a shell-hole behind enemy lines. He remained a prisoner until the war’s end in 1918.[58]