Jon Dimick III is the lord of Overtheway, a 7,200-square-foot shingled mansion with one of the best views of Mahone Bay in this seaside village on Nova Scotia's south shore.
The five-bedroom, seven-bathroom home, painted green with an elegant "French" elevator (to move heavy luggage) and covered verandah, has been in Mr. Dimick's family since his great-grandfather, Andrew Anderson, a doctor, philanthropist and former mayor of St. Augustine, Fla., built it in 1905, employing more than 200 craftsmen, including local shipwrights. It got its name because it was just was just over the way from a friend's property.
In late August, before the "gin and Jaguar" set – as the wealthy Haligonians, Torontonians and Americans who summer in Chester are affectionately called – prepare to decamp, Overtheway will be the venue for a major political fundraiser.
Federal Liberal Leader Justin Trudeau will be at the house for a $500-a-ticket meet-and-greet. About 150 people are expected. The next day, Mr. Trudeau will be in the suburban Halifax home of local business mogul Mickey MacDonald for a smaller but more intimate event: 75 to 80 guests, each paying $1,000.
In Atlantic Canada, Liberals are riding high in the polls, and Mr. Trudeau is attracting money, supporters and new people to run for his team. And in Chester, the Grits, who have traditionally been as scarce as Chevrolets on the village streets, see an opportunity to improve their fortunes in the next election.
Chester, renowned for its spectacular sailing, reliable winds on Mahone Bay and its August race week, which attracts hundreds of yachters and revellers from across North America, is part of the federal riding of South Shore-St. Margaret's. It is not known for electing Liberals.
"We've had a hard time recruiting candidates there, we've had a hard time raising money there, and this summer, we have the leader doing one of our biggest fundraisers of the year … in that riding," says Kirk Cox, the co-chair of the federal Liberal campaign in Nova Scotia.
They hope the largesse they plan to tap from some of the most powerful people in the well-heeled enclave can help deliver votes the riding in 2015.
Since 1968, only one Liberal has been elected there, and that was for one term – from 1993 to 1997 – in the Chrétien sweep. The rest of the time, Tories have ruled. In fact, in the 2011 federal election, the Liberal candidate was a distant third, earning less than 18 per cent of the vote.
But the popular incumbent, Conservative MP Gerald Keddy, is retiring, leaving the riding wide open for 2015 – and creating new possibilities for the Liberals.
Usually, Mr. Cox says, the Liberals are "lucky" to find one person, or maybe, two, to run for the nomination. But he believes people are seeing the party rebounding, getting organized and "they know if they decide to throw their hat in the ring it's not a long shot and there will be support for them, too."
Nova Scotia has 11 ridings – the NDP represents three; the Liberals and Conservatives each have four. One other Conservative incumbent MP, Greg Kerr in West Nova, is also not running again – another opportunity for the Liberals to gain a seat. The Liberals and Tories have each won seven elections since 1968 in that riding.
So consistently have the Trudeau Liberals been ahead in the public opinion polls in the province, however, that Don Mills, president of Corporate Research Associates, the regional polling firm, says: "The numbers suggest that no seats are safe for the Conservatives …"
In South Shore-St. Margaret's, one candidate, Jennifer Naugler, a young mother and school board chair, has already been "green-lit" by the national campaign team (after background checks and interviews) to seek the nomination. More are expected with the nomination meeting to be held in the fall, showing the increased level of interest in the riding.
The Harper Conservatives say they have "plenty" of serious potential candidates, but the nomination has not yet been opened.
Having a Trudeau in Chester, meanwhile, is not a new thing. Mr. Dimick says Mr. Trudeau's father, former prime minister Pierre Trudeau, came to the village for the summer to enjoy its scenery and hospitality. Even now, Chester is still full of famous faces, including a former bank president, a seafood billionaire and a magnate who made his fortune in moving and storage.
Mr. Dimick is a real estate developer, and plans to sell Overtheway soon. Playing host there to a party leader, and a Liberal one at that, is something new. His father, John Dimick II, was a dyed-in-the-wool Tory. Mr. Dimick says he votes for the candidate and not the party. But, he adds, "I'm not sure Harper is the guy."