A tax-law dream, ethical practice, and delivering justice in Canada's fraud-heavy landscape
This article was produced in partnership with Milosevic & Associates.
From the four walls of his bedroom poring over the works of philosopher Ludwig Wittgenstein, to the hallowed classrooms of McGill University’s Faculty of Law, to building a practice that aligned with his ethos, David Milosevic’s career journey has been anything but a straight shot.
Forgoing high school in favour of self-teaching literature and philosophy, Milosevic identified as “a very creative thinker who lacked discipline.” He attended law school to address that perceived shortcoming and was drawn to the rigorous area of tax law. But when the firm he articled with didn’t offer him a spot in its tax group, he decided he’d focus on travelling — it was tax law or nothing.
“Specifically, corporate tax law attracted me because it tested my thinking: it was an intellectual mountain to climb,” Milosevic explains, adding he climbed real mountains instead when he spent a year at a monastery in Nepal, meditating on his life course. Eventually, he returned to Toronto dead broke and, always one to relish a challenge, turned down an offer to join Scotia’s inhouse team in favour of hanging out his own shingle.
“I got a small basement office, and it was just me and my dog going in every day,” he recalls. “I took everything from Immigration and Refugee Board hearings to a criminal trial for $500 — you name it, I did it. But I gravitated towards financially complex fraud cases. They present a puzzle I enjoy solving.”
Eventually Milosevic landed a large securities litigation file two weeks before trial against the Ontario Securities Commission, kicking his evolution as a litigator into high gear. Now situated on the 36th floor of Scotia Plaza — a far cry from its humble basement beginnings — Milosevic & Associates is a new player in the litigation environment of downtown Toronto that’s already making a name for itself. It boasts nine lawyers, four assistants, and a stellar reputation as the emphasis remains on delivering tight and focused service.
“I see myself as in the same situation as before, just with more files and the support of a dedicated and talented team. It’s not just me and my dog anymore,” Milosevic quips. “We’re at an accelerated growth point right now, things are going well, and we’ve just got to maintain what we've done that's got us here so far.”
Milosevic & Associates are comfortable handling complex, high-stake cases like multi-party investor loss claims, civil fraud disputes, and oppression remedies. The firm is able to maintain its niche focus in large part because there are an increasing number of these types of files.
“Canada is an epicentre of fraud,” Milosevic says. “Unfortunately, our population is targeted by fraudsters worldwide because the penalties here — and the ability of the police to arrest and Crown to prosecute — aren’t what they could be. Authorities are overwhelmed.”
This area often leads to large group actions and the firm currently handles claims that range from a few dozen people to 434 people. Managing that many people involves town halls, where the lawyers must instill confidence in the group and keep them moving towards the same target — no simple feat. In fact, the cohesiveness of the group is the biggest challenge.
“When I do initial consults, I tell the people that in my experience the ones that work are groups that are motivated to come together quickly — there’s an energy to them,” Milosevic explains, adding that unity is key because if some stand to get more compensation than others, for example, it’s easy for things to fall apart.
“If that happens, then for defendants, it's easier. They can pick off parts of the claim and suddenly the strength of the case and the threat that it poses changes.”
Milosevic & Associates has achieved excellent results for plaintiff groups and its competitive advantage is simple: everyone is a straightshooter. In those town halls, the aim is never just to land the file, it’s to ensure the group sees that this firm will deliver information about the case “whether they like it or not.”
“People will retain you if they know they’ll get the facts, both good and bad, and can trust what you tell them,” Milosevic says. “That’s why I believe these cases are working for us — it's the way we approach them.”
Milosevic is also big on ethics, harkening back to the philosophical learnings he carries with him to this day. Calling himself a broken record, he tells his juniors “if you’re ever wondering what to do — should I disclose this to the court or opposing counsel, should I share this bad news with the client, is this bill fair — the answer is always the same: ethics.”
In his recruiting, Milosevic seeks out others who enjoy the demanding work and are also driven by the same code of professional ethics, because that’s the reputation he’s keen on perpetuating — especially given the kind of work the firm takes on.
“We do a lot of injunctions ex parte, where the judge is relying solely on us to stand in front of them and tell them what we’re doing,” Milosevic says. “We successfully obtained over a dozen Mareva injunctions last year and our reputation for delivering straight facts was no doubt crucial in those results. Litigation is local, and how you conduct yourself can open doors or close them in this profession.”
In that first big case Milosevic took on, he was quite literally relying on it to pay the rent. He remembers standing in a windowless room shoulder-to-shoulder with his new client, sorting documents into either a disclose pile or a do not disclose pile. One document could hurt the case badly, but it was clearly relevant, so Milosevic added it to the disclose pile. Wordlessly, the client reached out, moved it to do not disclose, and moved onto the next document.
For Milosevic, it was a fork in the road. He knew he risked losing the file, but he recognized even at that early stage that he wanted to be known for his ethics. He reached out, without a word, and moved the document back to the disclose pile, and kept going. Ultimately, Milosevic believes it gave the client more trust in him.
“Maybe under different pressure or on another day, I would have chosen differently and become a different kind of lawyer,” Milosevic says. “But I didn’t. It built that ethical practice, and that foundation became secure. My advice to young lawyers is always the same: don’t take shortcuts with your reputation.”
With a lot of files on the go currently, the goal in 2025 is to ensure everything is functioning as tight as possible and then focus on expansion. The future holds more lawyers, more services, and, if the Milosevic & Associates team has anything to say about it, more justice for victims.
“The drive of what I do is mostly intellectual, but over the last few years the cases have become more personal for me,” Milosevic says. “If I don’t get our clients their money back, they’re not getting it back — I’m often their last chance. There are so many victims who deserve compensation, and my focus is on serving them well and getting them some degree of justice that can be hard to get in these cases.”
