Mount Royal riding includes the two municipalities with the highest density of Jews in Canada, a group the Tories have fought hard to court since taking power in 2006.
With the federal election looming in October, no fewer than four cabinet ministers have visited Mount Royal since August, while Prime Minister Stephen Harper lit a candle at a Hanukkah ceremony there in December.
Another major election issue in the riding stems from the fact Mount Royal is home to some of the largest pockets of Quebec anglophones, who for years have complained about their linguistic rights being ignored.
The riding, which last elected a Tory in 1935, is the only place in Montreal where the Conservatives finished better than third place in 2011.
Popular Liberal MP Irwin Cotler, who has represented Mount Royal since 1999, is not running again.
He won by fewer than 2,300 votes in 2011 against Conservative candidate Saulie Zajdel, who has since been arrested on fraud charges related to his work on municipal council.
Mount Royal is at the geographic heart of Montreal and abuts Liberal Leader Justin Trudeau's Papineau riding as well as NDP Leader Tom Mulcair's Outremont.
Trudeau, whose father represented the riding between 1965 and 1984, could well see his foreign policy tested with the Tories hoping to capitalize on the perception among some voters that the Liberals don't sufficiently support Israel and are weak on terrorism.
The man tasked with holding down the shaky Liberal fortress is Anthony Housefather, who for the past nine years has been the mayor of Cote Saint-Luc, a Jewish-majority municipality in the riding.
He rejected the idea that the Conservatives' pro-Israel public stance has provided them with any advantage since 2011.
"In 2011 the Jewish community was very well aware that (Foreign Affairs Minister) John Baird, Harper and Jason Kenney were 100 per cent for Israel and that Kenney showed up at every Jewish event everywhere in the country," he said.
"There is nothing different since 2011 that didn't exist before."
Trudeau's popularity will bring out more Liberal voters to the ballot box, Housefather said, adding the NDP vote that more than doubled in the riding in 2011 will likely bleed to the Liberals.
"(The NDP) will never achieve (its 2011 Mount Royal result) in this election and that vote will almost certainly go Liberal, not Conservative," he told The Canadian Press.
The Conservatives have yet to choose their candidate.
Two well-known anglophones have publicly declared their intention to run for the ticket, while Montreal La Presse has reported that former TVA journalist Pascale Dery is also set to announce her candidacy.
Dery did not return calls.
Robert Libman, the mayor of Cote Saint-Luc for eight years before Housefather, already has Conservative-blue bumper stickers printed with his name.
He said the main reason the riding stayed Liberal in 2011 was Cotler's popularity.
"Irwin Cotler garnered a number of votes because he was Irwin Cotler — and Anthony is certainly no Irwin Cotler," Libman said in a tone that belied a strained relationship with his would-be opponent.
Housefather added to the perception that a tilt between himself and Libman wouldn't be the most congenial.
"On the day I was nominated (my two opponents) had two different things they did," Housefather said. "One called to congratulate me and the other called for me to resign (my mayoralty)."
The man doing the congratulating was Beryl Wajsman, who is also in the mix to run for the Tories.
Wajsman is the well-known editor-in-chief of The Suburban, an activist-style, staunchly pro-Israel weekly popular in the city's anglophone neighbourhoods.
Trudeau's opposition to Canada's current military role in Iraq, coupled with the perception among some Jewish voters that the Liberal support for Israel is tepid, will help the Tories win the riding, Wajsman said.
"Harper continued a policy of making clear to the world that this country stands with a democratic ally," said Wajsman.
"When Harper says that extreme Jihadism, as he puts it, that we are all facing, is something Israel has faced with every breath of its existence for 65 years — that matters. This guy gets it."
Housefather admits that past Liberal governments — particularly with their stance at the United Nations — have given the perception Canada has not stood strongly enough with Israel.
But the Liberals have changed their approach to the Israel-Palestine conflict, Housefather said, adding that Jewish voters in Mount Royal will come to understand that Trudeau is "very supportive" of Israel.
Israel isn't the only issue of the campaign.
The riding's majority of non-Jewish voters, particularly in its poorer parts, include large percentages of black and Filipino voters.
The issue of minority language rights ties the five disparate neighbourhoods in Mount Royal together.
While Housefather and Wajsman have histories of championing anglophone rights in Quebec, Libman stands out.
Libman created the provincial Equality party in the late '80s and led it to success in four anglophone-heavy ridings in the 1989 election.
He is known in Mount Royal as the man who fought the Liberal government's decision to invoke the notwithstanding clause to overrule a Supreme Court judgment aimed at invalidating part of Quebec's language laws.
"There is a large mosaic of cultural communities (in Mount Royal) that feel powerless sometimes at provincial and federal level and I feel I can deliver that representation that has been sorely lacking," he said.
Both Libman and Wajsman welcomed reports that Dery will enter the race and neither said they thought the Conservatives will favour any one candidate.
A spokesman for the Tories' Quebec wing told The Canadian Press the Mount Royal nomination process will be open and fair.
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