Sheila Kussner just raised another $7-million for charity. Her secret? She’s really good at asking Montreal’s elite to donate

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For a certain kind of well-heeled Montrealer, a lunch invitation from Sheila Kussner is a mixed blessing.

On the one hand, it means you are somebody in this town – you have made the fabled Kussner Rolodex, so valuable it is in her will.

On the other hand, if you pick up the phone – some people pretend to be out of the country when she calls – you are about to part ways with a very large sum of money.

At 90, Ms. Kussner is the city’s premier fundraiser. She has made an art of putting her hand in rich people’s pockets for a worthy cause.

“I’m a socialist,” she says with a grin. “Robin Hood.”

The cause is unimpeachable: Hope & Cope, a charity that provides cancer patients with counselling from cancer survivors and professional staff, inspired by Ms. Kussner’s own experience of losing a leg to the disease when she was 14. The concept of peer support was ahead of its time when she launched the organization more than 40 years ago, and that work is still what motivates her.

But dollars, not just good intentions, are what make her effective, and she is quite candid about the best way to amass them. Not for nothing did she just score a record haul: $7.34-million and counting after a campaign to fund the charity’s endowment. She estimates that over the course of her career she has raised approximately $100-million.

Her approach, which involves equal parts charm, chutzpah and a private table at Milos, can make her seem like a cross between Mother Teresa and Hollywood superagent Ari Emanuel.

In fact, Ms. Kussner is neither a saint nor a tycoon, but a much more down-to-earth figure. The daughter of a Montreal insurance salesman, she simply has a knack for selling. “I’m selling a good cause,” she said.

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Her husband, Marvyn, was in the box business, making corrugated cardboard products. He financed his wife’s operation for decades, with only occasional gripes about expensive wine, before his death in 2013 at 83. Ms. Kussner keeps a candle lit for him near the front door of their suburban Town of Mount Royal home.

When it comes to fundraising, Ms. Kussner insists, “there’s no technique – you just have to know the donor.” But there is a technique, and she has it down cold.

First, the donors. In Montreal, Ms. Kussner knows them all. Her Rolodex – actually a series of small cardboard boxes full of flash cards lined up neatly on her desk – bursts with the private phone numbers of local tycoons. The letters B (as in Bronfman and Birks), M (for Molson) and S (for Saputo) are especially thick.

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“I think the CIA would like that Rolodex,” said Suzanne O’Brien, the chair of the charity’s board – and the person who actually gets it in the will, so she can continue fundraising.

The city’s good and great are not big fish to Ms. Kussner but often friends, and she takes delight in discussing them. “I’m not name-dropping,” she said during a recent interview. “Okay, I am.”

The cookies she was serving? Those are the favourites of Aldo Bensadoun of Aldo shoes. Former governor-general David Johnston would be calling later in the afternoon as well. He and Ms. Kussner became close when he was principal of McGill University and she was raising $30-million to found the school’s oncology department.

When she talks about Pierre, she means Pierre Trudeau. They had a standing lunch date at the Ritz-Carlton. She always paid the bill. “He was cheap!” Ms. Kussner said. “But I loved him, he was a great man.”

Being well connected is half the battle – but only half. A skillful fundraiser also has to do their homework, Ms. Kussner said. What information provides that decisive edge? She put her hand to her mouth, mock-confidentially: “How rich they are!”

That doesn’t just mean how rich in general, but how rich that week. If she knows a prospective donor is heavily invested in a particular stock, she will make sure it hasn’t just taken a nosedive. She considers other personal details, too, in case the timing is bad for a big pitch – a death in the family, say.

“She has a fine sense,” Ms. O’Brien said. “We’ll make our little hit list, but she’ll say, ‘No, I don’t think it’s the right time. Let’s let them walk a base.’ … She’s not out to fleece you.”

The ask – as it’s known – finally happens after an elaborately choreographed courtship. For years, Ms. Kussner did her asking at the Ritz-Carlton. She knew the doorman, the maître d’, the sommelier. (After a good day, she tipped them double.) Before even sitting down, she learned if her donor liked red or white wine and wasn’t afraid to order a particularly nice bottle of Meursault if she thought it would help seal the deal.

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Now she does her asks at Milos, a white tablecloth Greek place in the city’s Mile End neighbourhood with valet parking. Ms. Kussner enters through the back and makes her royal progress to a choice table that is, according to a recent biography, reserved for just three prominent Montrealers.

This is when she lays on the charm and chutzpah, asking about your grandchildren, your business and, if she’s feeling especially brash, more intimate areas of your life. A photo in her office shows her and Pierre Trudeau together at a gala, laughing wickedly. She had just made a joke about circumcision.

Ms. Kussner’s gift for human connection keeps the city’s elite not just willing but eager to give her money. One wealthy Montrealer recently sold his business for a cool $17-million and was downright disappointed that he didn’t get an immediate fundraising appeal.

“He called me – he said, ‘Sheila, where were you?’” she recounted with glee.

“It’s a magical touch that I haven’t seen in too many big fundraisers,” Ms. O’Brien said. “A lot of these donors could just send her the cheque from their office. ‘What do you want, Sheila, 50,000, 100,000?’ But they line up for dinner because it’s the best dinner you’ll have.”

Ms. Kussner pays for the dinners out of pocket. The Kussners were not philanthropy rich, just comfortably upper-middle-class, thanks to her husband’s business success.

Marvyn also inspired the substance of her work. Although Ms. Kussner’s left leg was amputated during her teenage battle with bone cancer, it was her husband’s cancer diagnosis in his 40s that prompted her to launch Hope & Cope, after realizing how little emotional and logistical support was available to cancer patients at the time.

“Cancer treatment was slash, poison and burn – there was this very medical lens,” Ms. O’Brien said. “A doctor’s not going to tell you where to buy a wig – that’s just not in their ballpark – but for a woman who’s losing her hair, that can be life-changing.”

The charity has now helped more than 40,000 patients through the Jewish General Hospital in Montreal and a nearby wellness centre opened in 2007.

Despite her age, Ms. Kussner has hardly slowed down. She may now use a wheelchair after a lifetime of walking with a prosthetic, but she keeps Herculean hours, often working until 6 or 7 in the morning. Her time is filled with fundraising work, such as sending carefully personalized thank-you notes on expensive Crane & Co. stationery (she is an “addict,” Ms. O’Brien said, often writing “thank-you notes to thank-you notes to thank-you notes”), but also volunteering for the charity herself as a peer mentor. One patient calls her to chat at five every morning.

Although the foundation is now, naturally, planning for a “post-Sheila future,” she feels she’s just hitting her stride. Breaking $7-million during her latest campaign was an unexpected coup.

“I’m raising big money now,” she said proudly.

There’s nothing wrong with small money either, Ms. Kussner maintains. She is plenty grateful for any donation, if it’s what the person can afford. On a recent afternoon, an envelope came through her mail slot with an encouraging thunk: a card and cheque from a donor. But was it a good one?

“Two-fifty,” she exclaimed. “You better believe it’s a good one!”