In August 2019, Leary became a Canadian citizen.[2][5]
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.[1]
York Regional Transit
In 2009, Leary moved to Canada to become the general manager of York Region Transit in Ontario.[6] Leary was praised as ridership grew by 4 million while customer complaints reduced and vehicle reliability increased.[7]
Toronto Transit Commission
In 2014, Leary was hired as the chief service officer of the Toronto Transit Commission (TTC) by then-CEO Andy Byford.[8][9] 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,[10] improving the quality of service.[11]
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.[12] In July 2018, Leary's interim position was made permanent, following an international search.[13][14]
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.[15][16]
On June 20, 2024, Leary announced that he would step down from his position as CEO of the TTC at the end of August.[15] 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.[15] 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.[17] Deputy CEO Bruce Macgregor acted as CEO until former Metrolinx executive Gregory W. Percy was named interim CEO while a replacement is sought.[18][19]
^"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.
^"Rick Leary". coupler.ttc.ca. TTC. Retrieved 9 November 2022.
^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.'
^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.
^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.
^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.
^"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.
