Alan Slobodsky was a soft-spoken guy who never lost his cool. Slobodsky, who passed away in July at age 54, may not have been a household name, yet he was one of Toronto’s most effective city builders.

As ex-chief of staff to former Toronto Mayor Mel Lastman, and as a development industry consultant and advisor, Slobodsky developed a reputation as a master consensus builder.

"Alan was the fixer who quietly worked behind the scenes to get approvals and make projects work,” recalls Toronto Deputy Mayor Denzil Minnan-Wong. “Alan was the bridge between public servants, politicians, the Mayor’s office and developers. He brought people together to build the city."

Slobodsky, who had a degree in urban planning, was hired as an aide to Lastman while Lastman was mayor of North York, prior to its amalgamation with the City of Toronto in 1997. When Lastman became mayor of Toronto, Slobodsky followed him, and from 2000 to 2003, served as Lastman’s chief of staff.

“He always kept his word and was committed to the job,” Lastman says. “We met every Sunday to go through the whole agenda for the week.”

Lastman says one of Slobodsky’s gifts was being able to explain complex issues in a way everyone could understand.

“He did all the lobbying with members of council. He would meet with each one of them to discuss an item I was interested in and thought would be in the best interest of the people. If he didn’t get their vote, he’d just say thank you. He was always respectful, never nasty. Everyone liked him.”

Lastman says Slobodsky played a key role in helping bring the vision of a vibrant downtown to North York.

“That plan was done with Alan, myself and the ratepayers,” says Lastman. “It was amazing. We were putting a downtown in their backyards and not one person opposed it.”

After leaving city hall in 2003, Slobodsky opened his practice as a consultant to developers.

Jack Winberg, CEO of the Rockport Group, sought out his services after Rockport bought an old Art Deco post office in Toronto as a site for a mixed-use development, Montgomery Square. It was a politically charged project, as local residents considered the post office a neighbourhood gem. Winberg hired Slobodsky to help navigate the politics at city hall.

True to form, Slodbodsky was effective in coming up with solutions and achieving consensus. He was able to get the ratepayers on side with Montgomery Square (the old post office and a parkette were preserved and incorporated into the development), and by doing that, managed to convince the local councillor to support the project.

“He was a first-class advisor and, because of the way he did things, he had the confidence of everyone at city hall,” says Winberg. “He became a trusted advisor, and it was a relationship I treasured. He had great political insight, and great insight into people. His phone calls would get answered. When I needed advice or to move a file forward and could get nowhere, he had that touch. He had a wonderful feel for the city.”


Even after Lastman left the mayor’s office, they remained close, talking on the phone twice a week and meeting for lunch once a month. Lastman says as dedicated as Slobodsky was to his work, he was also devoted to his wife Rochelle, and their children Jonathan, Alyssa and Tara.

In his typical, quiet fashion, Slobodsky never let on how serious his situation was after being diagnosed with pancreatic cancer.

“When he got ill, I was on the phone with him every night,” says Lastman. “I still can’t believe he’s gone. He was my best friend.”