Maxwell spurned multiple offers to turn professional and ultimately quit playing hockey when he learned some of his peers at the senior amateur level were getting paid.

[1] He began his senior career in 1909–10, appearing in one game with the Winnipeg Monarchs of the Manitoba Hockey League (MHL).

[4] Maxwell scored three goals and two assists for the Monarchs in the 1913–14 season as the team won the city and provincial championships.

[2] By virtue of the title, the team was granted possession of the Allan Cup, emblematic of Canada's national senior-amateur championship.

The team initially refused to defend the trophy against a challenge by the Kenora Thistles after the Cup's trustees ruled Dick Irvin ineligible.

[5] The game, held March 11, 1914, was ultimately played and Maxwell's speed and skating helped lead the Monarchs to a 6–2 victory.

[7] The Monarchs repeated as Manitoba provincial champions in 1914–15 as Maxwell again scored three goals and two assists during regular league play.

The victory also earned his team the right to represent Canada at the first Olympic ice hockey tournament at the Summer Games in Antwerp.

[3] The Toronto Maple Leafs attempted to sign him to coach their National Hockey League club in 1931, however team owner Conn Smythe chose to hire Dick Irvin instead after Maxwell insisted on a three-year contract.

[3] In the Memorial Cup final, Maxwell's squad lost to the eastern champion Sudbury Cub Wolves.

He frequently officiated matches in both Allan and Memorial Cup playoffs, as well as professional teams that traveled through Western Canada.

[2] He was known for his quick, and often barbed, wit; His friends often told a story of an Arenas baseball game where, after failing to convince the umpire that it was too dark to play, Maxwell sent his players onto the field with lighted candles.