An Interview with Jack Winberg, CEO of Rockport Group

Fuller Landau team • June 22, 2018

Having recently celebrated its 60th anniversary, Rockport Group is a fully integrated real estate services provider that has played an integral role in the growth and development of the Greater Toronto Area. Handling all aspects of land acquisition, development, project and construction management, and income-producing property management, Rockport pioneered the condominium concept in Ontario, and has developed over 25,000 residential and retirement units. Recently, Rockport’s involvement in the Weston Common Development Project has shown the benefits of collaboration with the community.

Patricia Harris, Valuation and Litigation Partner at Fuller Landau, sat down with Jack Winberg, CEO of Rockport Group and son of the company’s original founder, for some insight on Rockport’s history, current projects, and the real estate industry in general. Here’s what he had to say:

Fuller Landau (FL): 60 years in business is a big milestone. How did Rockport Group get its start in the real estate industry?

Jack Winberg (JW): My father, Burt, started the company back in 1957, building single family homes in the then nascent Guildwood Village. Some of my earliest memories are of driving around construction sites with my father, meeting with project superintendents. My dad understood “affordability” in the old fashioned way.  He used to say, “There are more people who can afford Volkswagens than Cadillacs.” He always delivered the best quality at an affordable price, and the company has stayed true to that core value. In the late ‘60s, Ontario introduced Condominium Legislation, which prompted my father to sell all of the townhouses he was then building. That allowed him to deliver a less expensive home, turn money over faster, and build more. In the course of 15 years, my father built thousands of townhouse condominiums in Toronto.


FL: Did you join the company right out of school?

JW: After graduating from University, I went to law school while my father continued to grow the company and build out his legacy. I had the privilege of being mentored by some of the best legal minds in Canada.  I specialized for several years in land use and development, before joining Rockport Group in the late ‘80s. It was an interesting time – I started at Rockport at the peak of market before it dove into the deepest recession we have had in now two generations.


FL: How did the recession of the early 90’s affect the company, and your career in particular?

JW: I spent the first 5 or 6 years of my career at Rockport trying to hang on while sliding down a greased hill. It was a “trial by fire” experience for me. We survived, but I knew that we had to diversify our portfolio. We got into the self-storage business which experienced a huge demand as houses were getting smaller. We developed the land around one of our golf courses. We converted large vacant warehouses into industrial condominiums; we developed shopping centres; and we began to develop our interest in retirement homes. We made the strategic decision to get out of holding vacant land. From 1995 onward, there was nothing on our balance sheet that wasn’t either income-producing or work in progress.


FL: And you continued to branch out, after the recession?

JW: After the recession, we built our first high-rise condominium, which allowed me to put into practice my expertise as a developer. As time went on, we moved into more intense development – common element Townhome communities and midrise buildings. A lot of the traditional builders wouldn’t touch these projects because they were too complicated. Our next big move was to get into the retirement home business, which has since become a significant part of our portfolio. We currently partner with Amica.


FL: The Rockport Group has been involved in the Weston Common Project, which garnered a lot of attention in the press. Tell us more.

JW: This is a very exciting and interesting project for Rockport. A few years back, the City of Toronto developed a list of communities that need improvement and assistance. The Weston neighbourhood was at the top of the list with a higher unemployment rate than the city average, a scarcity of affordable housing, and a lack of access to services and amenities. It’s an area of Toronto that hasn’t had any sizable development for 40 years. There were hopes that the new UP Express and GO station would spur development; but that was just the start. A City-led charrette indicated  that an artist-based community hub would help with the revitalization of the neighbourhood. Our contribution includes  creative programming space, affordable live/work housing spaces for artists, a 370-unit condominium, and an outdoor area for the Weston Farmers Market and other public gatherings. We’ve worked closely with the City of Toronto; The Toronto Parking Authority, and Artscape to bring the plans to life. We’ve had all hands on deck for this project. It’s slated to open later this year and has taken a remarkable effort to get done. We’re proud of how it’s come together. In fact, the project has become a potential business model for the other in-need communities on the City’s list. We have to get better at producing affordable family housing in Toronto and making the most of our urban resources. This project is a huge leap in the right direction.


FL: To what do you attribute Rockport Group’s success? What is the company’s competitive advantage?

JW: I would definitely say that our size and nimbleness serve us well in the market. We have a great productive capacity with planners, builders, accountants, and property managers all on staff, making things work together. When we consider a property, we are able to bring to it a full range of development options, and we aren’t married to a particular type of development. We are flexible and always open to new challenges. As the markets shift, this gives us the ability to always stay busy.


FL: What’s in store for Rockport, going forward?

JW: As always, we continue to keep our eyes open for the changing landscape and any opportunities that may arise. We’ve never done the same thing twice and I don’t think it’s likely that we ever will. It’s important to me that we keep the work interesting – that’s key. Nobody in my office will ever tell me that they’re bored. We are always looking for interesting opportunities to build the City.

To learn more about Rockport Group, visit


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