Greek-Canadian businessman saw opportunity in undervalued Detroit real estate

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Andreas Apostolopoulos arrived in Canada as a 17-year-old on a Friday in 1969 and started work at a Kentucky Fried Chicken factory the following Monday. All his life he remembered the nine parts of a chicken that had to be rendered before they could be shipped off to a KFC outlet to be fried and dumped into a bucket.

A man who only went as far as Grade 5 or 6 in Greece, he was worth billions when he died on Feb. 15 at home in Richmond Hill, Ont., at the age of 68.

One of his biggest coups was in 2009 when he bought the 80,311-seat Pontiac Silverdome for US$583,000, about 1 per cent of the US$55.7-million cost of building the domed stadium in 1975.

Pontiac, Mich., is a separate city northwest of Detroit, but part of the Metro Detroit area. General Motors once built its Pontiac cars there, but like much of the Detroit area, it fell on hard times. The city of Pontiac built the stadium, home to the Detroit Lions of the National Football League, who played there until 2002, when they moved to the Ford Field in downtown Detroit.

That left Pontiac on the ropes. There was an offer on the stadium but the buyer reneged on the $250,000 deposit. There was an auction. The city was expecting US$17-million for its giant stadium sitting on 127 acres of land. Mr. Apostolopoulos was on vacation in Greece when one of his sons called him about the stadium sale. He made a stink bid of US$500,000. To his surprise he discovered he was one of the top three bidders. There was another auction and the auctioneer opened the bidding, over the phone, at US$20-million dollars. No one said a peep. Mr. Apostolopoulos won it for US$583,000.

For several years he and his three sons ran the Silverdome for everything from monster truck rallies to boxing matches. But a stadium that is one third larger than the Rogers Centre in Toronto can look a little empty with just 12,000 people in it. Then parts of the roof fell off, a problem with domed stadiums of the era.

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Finally, the stadium was demolished in December, 2017, and in 2019 the Apostolopoulos family came to an agreement with Amazon over the property – a confidentiality agreement prevents them from saying whether it was an outright sale or a lease. The end result is that the 127-acre property, at the junction of major highways, including the Interstate I-75, is home to an Amazon distribution and fulfilment centre. Amazon spent upwards of US$250-million to build the facility.

“My father turned down a lot of offers for the Silverdome, including a waste transfer station, until he found one that was good for the community. The Amazon site will provide 2,500 jobs better than minimum wage,” Peter Apostolopoulos said.

In 2017, Canadian Business magazine listed the Apostolopoulos family as the 22nd-richest in Canada, with assets of $3.9-billion.

Andreas Apostolopoulos, was born on Sept. 25, 1952, in Messini, Greece, where his father, Dimitri, ran a small café. His sister, Anna, moved to Toronto and then he followed. A couple of years after he arrived, the siblings sent for their father and mother, Dimitra.

Mr. Apostolopoulos, known as Andy in Canada, worked pulling chickens apart for a couple of years, so long that he met KFC’s Colonel Sanders on two occasions when the face of the company visited Toronto. In later life it was a bit of party trick that he could recite all the parts of the dismembered chicken.

He married Joanna Argiropoulos when he was 22. Her father, Peter, was a Toronto taxi driver and for a while Mr. Apostolopoulos drove cabs to the airport. He took on as many jobs as he could.

“He worked in his uncle’s fish and chips shop, he was an electrical apprentice and spent nights and weekends as an usher at the Titania theatre on the Danforth – which showed Greek movies – along with sweeping and mopping floors. He did it all,” his son Peter said.

Cleaning offices morphed into his first company when he landed his own contracts. His wife, Joanna, whose English was better than his, worked the phones lining up cleaning work.

“But he was the closer,” Jim said. “Our father was a very outgoing, friendly person.”

The links from one business to another seem obvious when looking back on his progress, but his first move up came when he thought he was paying too much for garbage bags. He decided to make them himself. Soon he was selling garbage bags to hospitals and other customers. He sold his cleaning contracts and started producing garbage bags full time.

Next he aimed to reduce the amount of rent he was paying for warehouse and manufacturing space for his garbage bags. He bought his first warehouse in East York, an old industrial area other companies had abandoned for Mexico, Vietnam or China. Right away he realized he had too much space for the garbage-bag business so he sub-divided the warehouse into units and rented them out.

The industrial rental business was much more lucrative than the garbage bag business, so he sold out and started Triple Properties, managing and developing industrial, commercial and retail space. He bought and sold one building after another. Because he used to rent warehouse space, he had a good idea what tenants wanted.

Like many immigrants, Mr. Apostolopoulos valued land and buildings more than other investments. Part of the reason was that in Greece, land was owned by the type of rich person he never thought he could aspire to be. “Buy bricks, not paper,” he told his three sons, who worked with him.

Though he had little formal education, he could work out a deal in his head in a hurry. “My father was very good with numbers. He was like a human calculator,” his son Peter said

The numbers on Detroit real estate looked good. In the early 2000s Mr. Apostolopoulos started looking at investing there. The city had been in a slump since the race riots of the summer of 1967 and again in April 1968, following the assassination of Martin Luther King Jr.

While buying a warehouse in Toronto gave him a 5-per-cent return on his money, buying an industrial property in the Detroit area produced a 20-per-cent return, since many developers avoided the area.

In 2012 Mr. Apostolopoulos bought the Penobscot office tower, a massive Empire State building lookalike in downtown Detroit for just US$5-million. Right away the annual rent brought in more than the purchase price. The 47-storey Art Deco Penobscot building has 1.25 million square feet of office space. By comparison, Scotia Plaza in downtown Toronto, at two million square feet, was valued at $1.5-billion in a sale in 2017.

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“A lot of people were afraid to invest. My father wasn’t afraid. Also part of the time he was buying when the Canadian dollar was at par with the U.S. dollar. At one point the Canadian was worth a bit more than the U.S. and that made buying in the United States even better,” Peter said. He added that there was negative press in the United States, critical of Canadians snapping up undervalued properties in the Detroit area.

One condescending article noted that Andreas Apostolopoulos spoke English with a Greek accent.

Mr. Apostolopoulos’s Triple Properties has faced criticism over the Penobscot’s state of disrepair. An article in the Detroit Free Press as recently as Feb. 8 noted the tenants in the building complained about a lack of water and elevator stoppages.

The City of Detroit issued 177 blight violation tickets and fines to Triple Properties for the Penobscot last year, according to the Free Press. Curbed Detroit magazine in a recent article, called Mr. Apostolopoulos “a controversial figure in Detroit real estate.”

The three brothers answered that the recent incident was caused by a power outage and failed water pump, which the brothers said was repaired within a day.

“The building is almost 100 years old and the previous owner neglected it,” Peter Apostolopoulos said. “We have spent millions updating the building.”

His father was always looking for new business opportunities. When he bought the Pontiac Silverdome, he noticed a small cheque came in that he and his sons couldn’t place. He learned it was a payment for a billboard on the site. From then on he was always on the lookout for properties with billboards.

One of his latest deals was building a huge casino, called Durham Live, in Pickering, a Toronto suburb. Its opening has been stalled by the pandemic lockdown.

“Our father was smart, sharp, quick-witted and a caring man, even more so as he got older,” his son Steve said. From the start Andreas Apostolopoulos was a frugal man, always a saver. “He was not flashy, did not care for name brands or look at what people had or what they were wearing as a marker for their character or worth as a human being, He had no biases, and couldn’t care less about your skin colour, social status, net worth or religion.”

He had no outside interests, apart from work and family, and no bad habits – didn’t smoke and was a light drinker – though he occasionally liked to play cards with Greek friends on the Danforth in Toronto. He was proud of his success and had one piece of advice: “You can’t get to the top without starting from the bottom.”

Mr. Apostolopoulos leaves his wife, Joanna; three sons, Jim, Peter and Steve; and five grandchildren.

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