Outgoing TTC CEO Rick Leary reflects on successes, regrets and the pressing need for more funding

TTC CEO Rick Leary for years has appeared before cameras to address major service-related issues often, but with just days to go until he leaves the Toronto institution it has become a time for reflection.

“I’m 61 years old and you start thinking about what you want to do next in life and you start thinking it’s about time personal change,” Leary told CityNews during a conversation outside his office at the Toronto Transit Commission‘s headquarters.

“I was about getting into the nitty gritty and making sure that we do the right thing.”

As government bureaucrats in Toronto go, the CEO at Canada’s biggest municipal transit agency is arguably one of the most prominent ones. After nearly seven years, Rick Leary will be stepping down on Friday.

Leary, who worked as a Boston transit executive and for the Region of York, joined the TTC more than 10 years ago after being recruited by former CEO Andy Byford.

“One of the things Andy did was bring me in to help fix the business, fix the operations — I’m very operational — and I love getting into that anytime there was a major event,” he said.

However, Byford and Leary both had different styles while occupying the top job at the TTC. Byford was known for being in front of the cameras and interacting with passengers while Leary seemingly leaned more into immersing himself behind the scenes.

“I’m not the one out there loading buses, right, saying hi to people. I’m the one in the subway tunnel making sure that we determine what the cause was so we can never have it happen again. That’s what I like to do and that’s what I was hired to do,” Leary said.

“I’ve let others do a lot of the media unless it required me to be out there. I was never shy.”

Questions have surrounded Leary’s departure from the TTC. In October, the TTC’s board launched an investigation into workplace misconduct allegations involving Leary. Any potential findings haven’t been released.

When Leary announced his resignation, Councillor and Chair Jamaal Myers was asked if the board forced him out.

“I can confirm that is not the case. Rick resigned to pursue new opportunities. You know, to break board confidentiality, we were all sad to see him go,” Myers said at the time.

CityNews asked Leary if he wanted to address any of the reporting surrounding his departure.

“As I said on June 20, when I announced I’m leaving on my own terms I feel real good about that,” he said.

“It took a few months of thinking, talking to my wife and family, you know, my parents, but I’m really happy.”

There haven’t been a shortage of issues facing Leary: Recent contract negotiations, the derailment of a Line 3 Scarborough RT train, cybersecurity issues, maintenance and state-of-good-repair problems.

However, he said one of the most major issues was the COVID-19 pandemic. The TTC had to keep operating to ensure frontline workers could get to their jobs.

“Nobody knew what was going to happen. We were no different,” Leary said.

He said it underscored how precarious the TTC’s revenue stream was.

“I used to talk a lot about, before COVID happened, about the reliance on the fare box and always warned people that having a 70 per cent farebox recovery. To me, that wasn’t a good thing,” Leary said.

“It just told me there was a lack of investment from other levels of government in the transit system.”

Another priority area for Leary revolved around a lack of diversity among the thousands of employees who work for the transit agency.

“This organization was 13 per cent women when I took over and I used to tell people that’s not statistically possible,” he said.

Leary said he and his managers worked to change policies, such as working to ensure at least four out of 10 new transit operators are women. He said a large majority of recent hires are racialized.

“This organization looks a lot different from when I got here. Now that I’m leaving, not everybody looks like me,” Leary said.

During the June 20 news conference announcing Leary’s departure, Myers said these efforts were appreciated by staff members.

“I heard from employees throughout the ranks that Rick was the most committed CEO the TTC has ever had to really improving diversity in the ranks, and that is a proud legacy,” Myers said.

When asked if he had regrets about things he wasn’t able to get done, Leary was quick to respond.

“You always want to do things faster. You want to make culture change faster. You want to get things done, things cleaner, customers’ experience. You want to change the training. I can tell you I’m very happy with what I’ve put in place,” he said, adding he was asked why he didn’t stay to help keep pushing for funding to replace Line 2 Bloor-Danforth trains.

“There’s always that one more thing you want to do, but you know, after seven years I think it’s time to turn it over to somebody else.”

Major funding needed to upgrade TTC infrastructure, maintain system: Leary

Outside the seventh-floor suite of executive offices where Leary has worked sits a lone plant with a small “money tree” sign, but it will take a lot more than that to realize the spending commitments needed to overhaul the TTC network. The top priority Leary alluded to was dealing with all the upgrades Line 2 needs.

“Line 1 is a little better shape with the [10-year-old subway trains},  the new signal system again which is five or six years old, but Line 2, you know, it makes me nervous,” Leary said.

“In 2026, [Line 2 subway trains] start turning 30 years old … we get incredible crews and talented staff here that will maintain them, but then it’s the signal system needs to be replaced. At the same time, the track. We still have asbestos in subways that we have to remove, a power systems upgrade. So there’s a lot of other things that have to do.”

Leary praised more recent investments and commitments from the City of Toronto and the Ontario government coming out of COVID-19, but the federal government hasn’t put forward the money needed to buy Line 2 replacement trains.

“I was excited when the prime minister came to Greenwood shops last month and we had a good discussion about the opening of the permanent transit funding that the federal government’s going to start preparing and distributing in 2026,” he said.

Advocates of the train replacement project have said the procurement process needs to start as soon as possible given the turnaround time involved with awarding contracts and building.

However, the needs extend beyond that one project. There have been several maintenance issues in recent years, such as the Line 3 train derailment, a hydraulic fuel leak on a TTC rail vehicle that caused a major temporary shutdown of Line 2, and a litany of restricted speed zones due to specification issues of various track segments.

When asked who is responsible for that and what needs to be done, Leary said it fell to him.

“I think ultimately, you know, it’s the organization that lies with me. I just call it what it is,” he said.

“We have to start getting to the core of what the problems are, and the lack of capital funding for state-of-good-repair.”

Standing alongside Myers and Toronto Mayor Olivia Chow on Tuesday, the trio announced another wave of enhancements to bus services across the city. CityNews asked about how continual bus crowding might be affecting TTC ridership recovery efforts.

Leary said he would like to see more dedicated “rapidways,” or dedicated lanes for bus travel, noting two have been put in place over the past five years. One of those installed was because the sudden closure of Line 3 required dozens of shuttle buses to keep up with passenger demand.

“I’d like to see more of those in that’ll provide better, more reliable service, less need for buses or better spread of buses, would also be very helpful,” he said.

Meanwhile, Leary had this advice for his successor.

“I’m trying to make sure that whoever comes in next understands the playbook that’s been put in front of them, and have them have the ability to move it on,” he said.

“It is about relationships at all levels of government. It’s about working with the unions, working with frontline employees. Enjoy the job, because you can make a difference here.”

Members of the TTC board are set to appoint an acting CEO on Wednesday while recruitment to fill the role on a permanent basis continues.