Determination, dedication and drive keep Dale Orlando at the top of his game

Dale Orlando’s mentor, John McLeish, had some advice for his protege at the beginning of his career: “As a young lawyer, your life is going to be a little bit miserable. You’re going to put your head down, be at the office for long hours and it's going to put a strain on your personal and family life — but when you pop your head up after a decade you’ll be amazed at how much you've accomplished and how far you’ve come.”

“I took that advice,” says Orlando. “For the first decade, I did everything I possibly could."

Orlando joined the Canadian Bar Association, the Advocates’ Society and the Ontario Trial Lawyers Association and began speaking at conferences, joining hearing committees, participating in lunch and learn dialogues and researching and writing papers. While it didn’t bring him much glory in the early days he took every opportunity to raise his profile within the bar and enhance his skills, eventually running for the board of directors at the OTLA and ultimately became president.

“I’ve dedicated myself to personal injury law essentially from the middle of articling,” says Orlando, principal partner at McLeish Orlando LLP. “And as a 10 year lawyer, I was ahead of many of my peers because I had done that. But the process continues — you can’t ever stop learning in this business.”

By the end of his articling year, spent with McLeish at the firm he was then a part of, the two “made fast friends” and saw eye-to-eye on most things. McLeish was known for his work in the personal injury field, and Orlando was mentored by him for three years, taking “a page out of John’s book” as he charted the course of his early career.

Eventually they decided to create a solely plaintiff-side personal injury firm where they could practice how they wanted, without any financial restraints put on them by other partners. Chasing payments, particularly from people who don’t have money but do have a need for representation and access to justice, was something Orlando found difficult, and he was drawn to “the beauty of the contingency fee system.”

“The firm finances the case — even if I need to spend $100,000 or more for engineering analysis, medical legal experts, life care plans, actuaries, accountants, you name it, I simply do it,” Orlando says. “We’re never placing an additional financial burden on our clients.”

In 1999 McLeish Orlando was founded with one other lawyer and seven staff, and the duo began building the type of firm they envisioned. There were times they were figuring out their systems as they went, Orlando recalls, adding he spent a lot of time learning about the business side of the firm which “helped make our operation efficient and productive.”

“It was such a unique time, such a small firm and everything was brand new — but it was exciting to be a part of it,” he says. 

The firm established itself as a forerunner in the field, with a laser focus on clients who come to Orlando and his team at a time when their lives have been shattered and they're extremely uncertain about what lies ahead. Acting as a calming influence and offering peace of mind when they need help the most is a point of pride, he says, and it forges a connection on a personal level that “extends well beyond the conclusion of the lawsuit.”

“I’ve made some good friends over the years by representing people — you’re involved in every aspect of their lives for a period of years as the case works its way through the system,” Orlando says. “You really become part of the family. I have clients whose cases resolved over a decade ago that still reach out.”

One case that sticks out for Orlando is Deering v. Scugog, where teenage sisters suffered spinal cord injuries in a vehicle rollover and were paraplegics. There was a motor vehicle insurance policy that would pay $1M, but given the severity of the injuries that wasn’t adequate. Representing one of the sisters, McLeish Orlando pursued the municipality of Oshawa Scugog, which was ultimately found to be significantly responsible for the cause of the accident because the road was in a condition of non-repair. The sisters then had access to the municipal insurance policy, which is essentially unlimited. Though it was hard fought over several years — it was appealed to the Court of Appeal and there was a leave application to the Supreme Court — the firm prevailed, and the sisters were able to access the care they needed and live with dignity.

Over two decades since its inception, McLeish Orlando remains a small but mighty firm with a family feel, and Orlando says he’s still learning — and doesn’t intend to ease off the throttle anytime soon. He predicts he has “at least another decade left in me, and a group of younger partners who are excellent lawyers and embody what’s important and what our firm stands for: dedicating yourself to excellence and doing everything you can to improve the lives of clients.”

While both the firm and the legal landscape have gone through some changes — McLeish is now semi-retired, and culturally there’s been a shift away from seven day a week, 12 hour a day work weeks — the foundation upon which McLeish Orlando was built still stands.

“You have to make sacrifices if you want to excel in this business — it’s a super competitive field, and there are a lot of good lawyers and firms competing for the same pool of clients,” Orlando says. “You have to have a reputation to be retained, and be able to do the job. It all goes back to putting your head down and dedicating yourself to obtaining the skillset required to represent people who are looking to you as a lifeboat. You don’t want to let them down.”

This article was produced in partnership with McLeish Orlando LLP.