Flags were at half mast at Westmount city hall Friday to mark the passing of May Cutler, the city's first female mayor.

Cutler was hospitalized last month and passed away Thursday at her Westmount home. She was 87.

Cutler served as the city's mayor for just one term from 1987-91, but Montreal city councilor Marvin Rotrand said her arrival changed the political culture in Westmount.

"Westmount was noted for having a chummy political inclass that had run the town since it had been founded at the end of the 19th century," Rotrand said. "For a woman and outsider to win seemed a bit unusual, and I know some feathers were ruffled in Westmount."

Current Westmount Mayor Peter Trent says Cutler had exactly what it took to clear that gender hurdle with ease.

"She proved the adage that to be a woman and succeed you have to be twice as smart as a man," Trent said. "And boy, she was twice as smart as any man I've met."

Trent credits Cutler for bringing him back from England to get back into politics.

"She phoned me and said, ‘Peter I want you to come back on council, and when I step down as mayor I want you to run for mayor,'" Trent recalled. "I said, ‘May that's two years from now, and I supported the person who ran against you!'"

But Cutler didn't care, Trent said, she wanted him on her council regardless.

One of the last times he saw Cutler was at a public event last spring, and Trent said it typified what kind of woman she was.

"She was back from a trip to Antarctica," Trent said. "That's May. She doesn't go to France, she goes to Antarctica. At the age of 86."

Cutler was also a trailblazer in the publishing world, becoming the first female publisher of children's books in Canada when she founded Tundra Books and ran it for nearly 30 years. Among the countless authors and titles published under the Tundra name, perhaps none are as well known or as iconic as Roch Carrier's classic tale The Hockey Sweater.

Gazette culture critic Pat Donnelly remembers her good friend as a fearless woman.

"I remember calling her in New York right after 9/11 because she was there," Donnelly remembers. "She was very upset about the whole thing, but there was no question of her leaving the city or getting into a panic because of some mere terrorists."

No, it took more than that, or a seemingly well-entrenched old boys' club mentality, to scare off May Cutler.