Michael Russell | The Oregonian/OregonLive

Back in 1974, when Jim Sassalos bought the restaurant that would become the Overlook, it was a shambles, with cracked dishes, one bathroom and 35 mismatched seats.





And it was just what he was looking for.





On Sunday, the 81-year-old Greek immigrant will close the restaurant he has run for more than half his life at the corner of North Maryland Avenue and Skidmore Street. And when it goes, it will take with it one of Portland’s last true diners, a place where neighbors gather for all-day breakfast and never have to wait long for someone to refill their coffee.





Portland is home to lunch counters, hotcake houses, dives, breakfast chains and an endless stream of brunch spots, but few classic diners. Among those, the Overlook came closest to replicating the East Coast diner ideal immortalized by Edward Hopper and “Seinfeld” -- busy, inexpensive, often Greek-owned restaurants where customers sit at booths or long counters eating gyros, burgers and breakfast all day (or through the night).

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Michael Russell | The Oregonian/OregonLive

Four decades ago, Sassalos was working at the old Thunderbird Motel next to the Memorial Coliseum, not far from where he first docked in Portland as a radio operator with the Greek merchant marines. Six years earlier, after being sponsored for a United States visa, he landed in Portland and talked his way into a job at the hotel’s restaurant. There he soaked up the finer points of service and restaurant management. He was ready to be his own boss.







A friend told him that the old Devlin's Cafe on North Interstate Avenue was for sale. The asking price: $48,500. Sassalos had about $3,500, not enough for the down payment.



“I went to ask Boyd’s (Coffee) for financial help,” Sassalos says. “I knocked on the door. Two people came out, big tall men, Norwegians or Swedes, I think. I told them my story, and one of them looked down at me like this, because he was big, tall, and he said, ‘We don't do that here, but I'm going to help you.’ He gave me $1,500 of his own money.”



Sunshine Dairy chipped in $2,000, again with no questions asked, no paperwork and no timetable for repayment, Sassalos said.





Sassalos has served Boyd’s coffee and Sunshine milk ever since.

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Michael Russell | The Oregonian/OregonLive

At the time, the Devlin’s Cafe menu had about 15 items, including live and onions. The restaurant earned about $350 a day. Not bad, considering coffee cost 10 cents a cup. Within the year, Sassalos had sales up to $1,200 a day.



The dining room soon became so packed that Sassalos had to seat strangers together.



“If there were a table with two people, two empty chairs, I’d say, ‘Here's a new neighbor you've never seen before, but you know them now,’” Jim Sassalos says.



It was a practice that charmed his future wife.



“I was working across the street,” says Jane Sassalos, 69, who was born in Amity and grew up in the Valsetz logging camp. “I came over for lunch, a single woman, and I'd get soup to go. I was too shy to sit in. But soon, Jimmy started seating me with people. He was good at figuring out who should sit with who.



“That was 1979. By the spring of 1980 we were married.”

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Michael Russell | The Oregonian/OregonLive

All the while, Jim Sassalos was planning for the future, quietly buying up houses on all sides of the restaurant.



“We didn't want a McDonald's,” Jane Sassalos says.



By the 1980s, he was able to begin expanding the restaurant, adding more seats in the dining room and a neighboring lounge with two gas fireplaces. A neon sign was added in the early 1990s.



After the Overlook closes, the lot will make way for a pair of five-story apartment buildings, in line with the changing character of the neighborhood.



“All that development you see down on Mississippi there happend after the MAX line was established, it improved the whole area,” Jim Sassalos says.



Jane Sassalos plans to spend her retirement working on her art and raising money for charity. Jim Sassalos might garden at their North Portland home, or dabble in the stock market. The couple have three children together and one grandchild.



“Not full speed,” Jim Sassalos says. “I have enough reading done. I'm going to do that slowly, carefully, not because I want to make big money, I just want to keep my mind busy.”

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Michael Russell | The Oregonian/OregonLive

On Wednesday, Jim Sassalos walked the floor, as he often still does, talking with customers, running pancakes and waffles to tables and clearing dishes. Every seat in the restaurant was full.



“He’s that way every day,” says Doug Englund, sipping iced tea at the bar. “He’s got his finger on the pulse. He’s not an absentee owner. He’s right here and everything that happens he knows about.”



Englund says he’s been coming to the restaurant since the Devlin’s Cafe days.



“This is a place where all sorts of people can come, people in suits, people from the shipyards, people of all sorts of political persuasions. You’ve got the smart ones, and then you’ve got the ones who support Donald Trump,” he says, nudging friend and fellow regular George Buckley, who’s been eating at the Overlook for 25 years.

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Michael Russell | The Oregonian/OregonLive

Looking back on his own life, Jim Sassalos says he wants young people to know that there is still opportunity available for anyone, as long as they’re willing to work hard.



“I heard people talking about there is no American dream,” he says. “My experience is the American dream still exists. It’s still here, everywhere. And the people who don't see it are people who wanted to start at the top.”





The Overlook Restaurant will close its doors for good after service Sunday, January 21 at 1332 N. Skidmore St.



-- Michael Russell

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Over the past two weeks, crowds have gathered for final meals to the Overlook. Below, find some of their farewell photos.

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Read more

We collected 15 of our favorite remaining diners and diner-ish restaurants in the Portland area. Some might be better classified as hotcake houses or lunch counters, but all offer a slice of diner-style menu or decor.

Portland's 15 best (remaining) diners