Andreas Apostolopoulos
CEO of Triple Group of Companies remembered highly as a family man
was a Greek-Canadian business titan known for his ambitious projects here and abroad.
Greek-Canadian businessman Andreas Apostolopoulos began his storied career shortly after his family immigrated to Canada in 1969 from Kalamata, Greece.
Apostolopoulos, described by family members and friends as a kind and family-oriented man with a sharp business sense, passed away suddenly at his home on Monday, at 69 years old.
He was the chair and CEO of the Triple Group of Companies, having worked his way up from his first job in Canada as a labourer to the top of the real estate development game.
Along the way, he started an office-cleaning firm, followed by a plastic-bag manufacturing company, before building one of Canada’s largest privately held real estate corporations alongside his three sons, Jim, Peter and Steve.
Apostolopoulos leaves his wife, his sons, their spouses, and five grandchildren.
Jim Apostolopoulos described his father as someone who would always help out someone in need, who was careful with his money, and who worked hard to make his family happy. He always kept his word, Jim added, and taught his sons to treat everyone equally.
“The legacy he leaves is not just for the Greek-Canadian community, but for all immigrants coming to a new country,” he said.
“He measured success not by how much money someone made, but by how hard they worked to provide for their family.”
In 2009, Apostolopoulos made a splash when he bought the Pontiac Silverdome near Detroit. In an interview, he said he saw an ad for the stadium in the Toronto Star and decided to go for it, even though his company, 15 years old at the time, normally dealt in commercial and industrial real estate.
“It’s something different,” Apostolopoulos told the Star of the deal.
Jim Apostolopoulos said his father truly loved what he did, was always excited about “the deal,” and always seeing potential where others did not.
“He never lost this spark,” said Steve Apostolopoulos.
Apostolopoulos brought the stadium, which had been empty for eight years, back to life, spending millions on revitalizing it, hosting concerts and Monster Truck competitions. The site is now home to an Amazon fulfilment centre.
Three years after the purchase, the businessman was still betting on Detroit, buying the historic Penobscot building.
One of Apostolopoulos’ biggest projects is still in development: Durham Live, a casino and entertainment complex in Pickering, which was announced in 2015.
Steve Apostolopoulos said his father was also an avid game show fan, especially “Wheel of Fortune”: “Even though his English wasn’t perfect, we would often catch him yelling at the TV to ‘buy a vowel.’ ”
Richard Chilcott, an investment broker and principal with the Avison Young Capital Markets Group, first met Apostolopoulos in 2004, when his firm sold him an LCBO.
Apostolopoulos struck Chilcott right away as “incredibly humble.” Over the years, he said this only became more apparent — as did his sense of humour and keen business acumen.
What may have seemed like a lucky instinct to outsiders was actually a sharp intellect and a natural talent for sussing out the potential of a deal, said Chilcott: “He had this innate ability to see the woods for the trees.”
Jim Apostolopoulos described his father as “brilliant and street smart,” despite the fact he had only finished Grade 6 in Greece.
“He was like a human calculator. When we discussed the numbers, the three of us would start to work it out on our calculators, and he already had the answer,” said Peter Apostolopoulos.
And yet, despite his long, successful career, Chilcott said he felt like Apostolopoulos was “only just getting started.”