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Richard J. Leary is an American-Canadian transportation executive who was chief executive officer (CEO) of the Toronto Transit Commission (TTC) between 2017 and 2024. Leary became interim CEO in 2017 and took over the role permanently in 2018; he resigned in August 2024. Leary was previously general manager of York Region Transit and held senior roles with the Massachusetts Bay Transportation Authority (MBTA).

Personal life and education

Richard J. Leary was born in Boston, Massachusetts. His father was a streetcar operator for the Massachusetts Bay Transportation Authority (MBTA). He graduated from Northeastern University with a BBA and an MPA. As well, he completed a graduate program from Harvard University in Administration and Management.

In August 2019, Leary became a Canadian citizen.

Transportation career

Massachusetts Bay Transportation Authority

Following his father, Leary began working for the Massachusetts Bay Transportation Authority as a subway attendant in 1984. He then moved through various manager and director roles, becoming the chief operating officer of the MBTA in 2005. He retired from the role in November 2009 after failing to appear at a board meeting to address a damning federal safety report.

York Regional Transit

In 2009, Leary moved to Canada to become the general manager of York Region Transit in Ontario. Leary was praised as ridership grew by 4 million while customer complaints reduced and vehicle reliability increased.

Toronto Transit Commission

In 2014, Leary was hired as the chief service officer of the Toronto Transit Commission (TTC) by then-CEO Andy Byford. This role involved management of the TTC's bus and streetcar systems, as well as management of the various Toronto subway stations. Leary's achievements included a large reduction in the number of short turns, improving the quality of service.

In December 2017, Leary was made the interim CEO of the TTC, when his predecessor, Andy Byford left to head the New York City Transit Authority. In July 2018, Leary's interim position was made permanent, following an international search.

In late 2023, TTC Chair Jamaal Myers attempted to have Leary suspended while an investigation into allegations of workplace misconduct took place. The board of the TTC agreed to launch an investigation, but did not suspend Leary.

On June 20, 2024, Leary announced that he would step down from his position as CEO of the TTC at the end of August. Leary noted that it was his decision to leave, having waited to announce his resignation until contract negotiations with Amalgamated Transit Union Local 113 had been agreed. Upon his departure, Leary noted that he had a contract until 2026, with the new mayor, Olivia Chow, and TTC Chair indicating a change in direction for the organization – however Leary reiterated it was his decision to leave the job. Deputy CEO Bruce Macgregor acted as CEO until former Metrolinx executive Gregory W. Percy was named interim CEO while a replacement is sought.

References

1. ^ Bierman, Noah (2009-10-10). "Top operating officer to retire, T confirms". Boston.com. Retrieved 2021-02-16.
2. ^ "TTC chief Rick Leary talks fighting racial bias, hiking fares and the future of Toronto's transit network". Toronto Star. 2019-12-29. Retrieved 2021-02-16. In what the CEO described as a "touching" ceremony in Scarborough on Aug. 13, the 55-year-old Boston native took the oath of Canadian citizenship.
3. "Rick Leary confirmed as TTC CEO". The Coupler. 2018-08-24. Retrieved 2018-11-04. Leary graduated from Northeastern University with a Bachelor's of Business Administration as well as a Master's Degree in Public Administration. Leary later graduated from Harvard University, completing the graduate program in Administration and Management. He is married with three children, the youngest of whom was born here in Ontario in 2013.
4. "Rick Leary". coupler.ttc.ca. TTC. Retrieved 9 November 2022.
5. Thompson, John (2018-11-03). "A Bostonian tackles Toronto". Railway Age. Retrieved 2018-11-04. On the personal front, Leary and his wife will soon be house hunting in Toronto, to end his lengthy commute from the outlying town of Aurora. 'We even have a little Canadian in our home; our five-year-old son was born after our move to Canada.' 
6. Kalinowski, Tess (2014-04-03). "TTC recruits York Region Transit head to help improve service". Toronto Star. Retrieved 2018-11-04. Leary joined York Region as general manager in 2009, after retiring from the Massachusetts Bay Transportation Authority. York contracts out about 20 per cent of its service to the TTC, said Leary.
7. "TTC recruits York Region Transit head to help improve service". Toronto Star. 2014-04-03. Retrieved 2021-02-16.
8. Spurr, Ben (2018-01-04). "TTC prepares 'Plan B' after delays to Bombardier streetcar order". Toronto Star. Retrieved 2018-11-04. In a wide-ranging interview in the seventh-floor corner office at TTC headquarters recently vacated by former chief executive officer Andy Byford, acting CEO Rick Leary said he was 'putting a Plan B together' in the event the streetcar order is not completed as scheduled.
9. Spurr, Ben (2018-07-09). "TTC board confirms Rick Leary for top job at Toronto transit agency". Toronto Star. Retrieved 2018-11-04. As the Star reported Monday, the hiring panel struck to find the next chief executive unanimously endorsed Leary about two weeks ago. The Boston native has been serving as acting CEO since December, after Andy Byford left to take a job as president of the New York City Transit Authority.
10. "Hate 'short-turns'? Here's how 'fresh eyes' at the TTC are putting an end to them". thestar.com. 2014-12-08. Retrieved 2021-02-16.
11. "Who is interim TTC CEO Rick Leary? - CityNews Toronto". CityNews. Retrieved 2021-02-16.
12. "Statement by TTC Chair Josh Colle". Toronto Transit Commission. 21 November 2017. Retrieved 2021-02-16. Finally, at our Board Meeting on Nov. 28 to discuss the budget, I will ask the Board to affirm our Deputy CEO Rick Leary as Acting CEO, effective Dec. 22.
13. Fox, Chris (2018-07-10). "TTC board appoints Rick Leary as CEO". CTV News. Retrieved 2021-02-16.
14. "Rick Leary to be next TTC CEO, city's transit chair confirms". CBC News. 2018-07-10. Retrieved 2018-11-04.
15. ^ Spurr, Ben (2024-06-20). "TTC CEO Rick Leary resigns". Toronto Star. Retrieved 2024-06-20.
16. Harvey, Lex; Spurr, Ben; Rider, David (2024-06-20). "Inside Rick Leary's TTC: Allegations of bullying and a secret meeting about the CEO's future". Toronto Star. Retrieved 2024-06-20.
17. Johnson, Natalie (2024-08-31). "TTC CEO departs top job two years early, amid 'new direction' at City Hall". CTV News Toronto. Retrieved 2024-08-31.
18. Callan, Isaac (28 Aug 2024). "Toronto transit agency names temporary new boss". Global News. Retrieved 2024-08-31.
19. Habibinia, Ben Spurr, Mahdis (2024-09-25). "Former Metrolinx executive appointed interim TTC CEO. 'It is an audition'". Toronto Star. Retrieved 2024-10-07.{{cite web}}: CS1 maint: multiple names: authors list (link)

• American urban planners
• People from Boston
• 1963 births
• Living people
• Northeastern University alumni
• Harvard University alumni
• American chief executives
• Toronto Transit Commission general managers
• American emigrants to Canada