The groundbreaking of the Trump International Hotel & Tower took place on a brisk day last October, at the southeast corner of Bay and Adelaide. It started with Donald Trump, six foot two including his hair, emerging from his limousine, then gamely posing with the cere­monial shovel. Standing beside Trump were several less imposing people. One of them was a youngish, compact, un-mogul-esque guy with a round, close-cropped head of hair and a manner both courteous and slightly sheepish; this was Alex Shnaider. The ceremony concluded, Shnaider politely shook hands with Trump and, as The Donald swept away, blended back into the scene, looking briefly like Woody Allen’s Zelig.

What Alex Shnaider didn’t look like was a man who had paid for the plot of land he was standing on, and had majority control of the $500-million, 60-storey tower. Nor did he look like someone who had purchased in advance the project’s uppermost 7,800-square-foot penthouse, valued at $20 million, making it the most expensive condo ever sold in the city. For the record, Shnaider’s other notable assets include a 15,000-square-foot Bridle Path mansion, a 250-acre King City estate and a $50-million private jet. Through his company the Midland Group (along with his partner Eduard Shyfrin), he runs a network of steel plants across eastern Europe, as well as seven trading houses, a shipping fleet, two retail chains and several business centres and malls.

Alex Shnaider may not look the part, but he is all these things. At 39, with assets estimated at more than $2 billion, he is Toronto’s youngest billionaire. That he could be that rich and remain anonymous isn’t the only contradiction he embodies. He is a mensch and a shark, a common man with an uncommon touch. He’s a stylish dresser who can look like a schlepper, a reflexively trusting man who is capable of pure implacability when he feels that trust has been violated. He is a quietly ironic man who can sound as pompous as anyone you’ve ever met. And he succeeds in pulling off these sleights of hand with a remarkable lack of phoniness. “Alex,” says his good friend Tie Domi, is just “a very, very, very down-to-earth guy.”

What Shnaider wasn’t counting on—and what has brought him unwanted scrutiny—is a scandal involving a Russian oil venture. His partners in the company have launched a number of civil suits citing him for breach of contract and claiming damages of more than $750 million. Shnaider is alleged to have bribed Russian police and hired armed thugs to intimidate a business associate—claims he states are “outrageous fabrications, without any semblance of truth whatsoever.” More pointedly, the charges have raised the spectre of a stereotype he’s spent much of his career trying to shake.

By the time people in this city realize who Alex Shnaider is, it may be for what he would consider all the wrong reasons.

When you’re a billionaire, the billion is the elephant in the room. How rich is rich? This year, Forbes magazine ranked Alex Shnaider the 553rd richest person in the world, but of the billionaires ahead of him, the vast majority are appreciably older. In Canada, Shnaider is in 15th place overall, and moving up fast.

Just as novel as his quantitative rich-person credentials, though, are Shnaider’s stylistic differences from the traditional template of extreme wealth in this city. A Russian émigré who arrived here with his parents at age 13, he’s a marked departure from the classic moneyed WASP dynasties: the Thomsons, Eatons and Rogerses. Old money in Canada has always had a staid Fifth Business quality, impressive but never exciting. In the past, for the Canadian rich to be daring or flamboyant with their money, they had to go elsewhere; witness Montreal’s Bronfman family. Shnaider may not be Donald Trump, but he’s not averse to asking the showy developer for advice (something he reportedly did before investing in a luxury resort property in the Dominican Republic), or to leading a jet-set lifestyle that may surpass even Trump’s in the details (until recently, Shnaider owned his own Formula One racing team, and this past winter he purchased the most famous soccer club in Israel). William Thorsell, the ROM’s CEO, likes to tout the fact that close to half of the museum’s New Century Founders—contributors of $5 million or more—weren’t born here: people like Michael Lee-Chin, originally from Jamaica; Shreyas and Mina Ajmera, from India; Jack Cockwell, from South Africa. And Alex Shnaider. Like his peers, Shnaider seems less concerned with breaking into the upper echelons of Canadian society than with raising his own status on the global stage. This is not your father’s rich guy.

The head offices of the Mid­land Group, where I met Shnaider, aren’t located in a predictably choice downtown tower, but in a medium-rise commercial building on Yorkland Road, in a suburban warren of industrial parks near Sheppard and the DVP. The decor is open and airy, but far from ornate. Shnaider fits right in. Thorsell calls Shnaider and his wife, Simona, “a very stylish couple,” citing Shnaider’s “great shoes and great suits.” But at our interview, wearing a blue sweater vest, with a five o’clock shadow, fresh from one European trip and about to depart on another, the billionaire looked like a small, weary, boyish guy who’s comfortable with his hands in his pockets, and maybe wearing slippers.

His route to Toronto was circuitous. Born in St. Petersburg in 1968, Shnaider emigrated as a toddler with his parents to Israel, and then to Canada with them 10 years later. His parents, professionals by trade (his mother, Sieva, was a dentist, his father, Fella, an electrical engineer), were both over-educated and under-experienced for the Toronto job market and ended up buying a small delicatessen in the burgeoning Russian Jewish neighbourhood near Steeles and Bathurst. The teenaged Alex worked in the deli, slicing meat and lugging cases of pop while he attended high school in North York and then nearby York University. He suffered the usual slings and arrows of being a new kid with an accent, but his surprising prowess in basketball (he tops out at five foot seven), along with his understated sense of humour, solidified his popularity. Ron Fine, a close high school friend, remembers speculating with Alex and another buddy of theirs, Danny Tilis, about where they’d be in 20 years. “As the verbose one, it was generally accepted that I’d end up in broadcasting or the media,” Fine says. “Danny was a details guy, and we assumed he’d end up in accounting. Alex was always so quiet about things. He had a terrific memory, and he was great with figures. We knew he was special. We just didn’t know what he was going to do.” (Today Tilis is the COO of the Midland Group, and Fine is the company’s head of communications.)