OscarsBy REBECA KUROPATWA The original Oscar’s Deli, which was started  by Oscar Berman in 1929, was nothing like what the restaurant looks and feels like today.

What used to be on the menu back then included corned beef, pastrami, and salami sandwiches, along with pickles and drinks. On the shelves behind the counter, there were a few groceries.
Berman owned the place until 1947, and the deli has changed hands three or four times before the Ludwig brothers (Asher, Sam, George, and Myer) bought it. “They ran it for a number of years until Myer decided it wasn’t enough for the four families,” said Oscar’s Deli’s current owner, Larry Brown. “So, he opened Myer’s Deli on Grant. The other three brothers stayed on Main Street.”
Changing of Hands: 1929 - 1991
In 1971, the Ludwigs sold the deli to their nephew, Jimmy Shukster, whose mother was a Ludwig. “Jimmy, at that time, called me and wanted to know if I wanted to join them,” said Brown. “I said ‘no,’ as I had been working with my father-in-law. Eventually, in 1979, I spoke with Jimmy to see if he was still interested in having a helper and he said, ‘yes.’ I worked there with him until 1982. Then, we opened this downtown location, at 175 Hargrave St.”
Between 1982 and 1997, Jimmy and his brother, Harold, ran both deli locations along with Brown. In 1991, Brown bought them out. The Main Street location closed in 1997.
Brown began upping Oscar’s menu offerings when he joined the Shukster brothers at the deli - starting small, with the addition of a turkey sandwich. “I don’t think we had ham until we moved to our Hargrave Stteet location,” said Brown. “Once we moved here, we started doing soups and salads, and they also started serving salads and soups at the Main Street location. I’d make the soups for them and they’d pick them up.”
Keeping family tradition
Brown’s daughter, Rachel, started spending time at the downtown location as soon as it opened. She was eight years old when she began clearing tables. In 1998, she joined her father at the deli full-time and has continued doing so ever since.
Of her experience working with her father, Rachel said she feels very fortunate for the opportunity, referring to it as, “irreplaceable.”
Rachel feels patience is the biggest trait she had to learn when working with her dad, adding, “I definitely surprised myself with baking. Who knew I could bake a carrot and chocolate cake that everyone loves? More than anything, it’s been a second home, second nature.”
New chef + downtown evolution =
revved up menu + hours
Until this past spring, when Chef Hari Haidau joined the Oscar’s team, the deli had gone without a deep fryer. “I’ve stayed clear of a deep fryer for 35 years,” said Brown. “Hari twisted my arm and we now have one. We now have fries, probably some of the best in the city.”
While the deli has been open for the morning and lunch crowd since its inception, Haidau saw an opportunity with the proximity to the MTS Centre to stretch the service into the dinner crowd.
“We’re basically looking to expand,” said Haidau. “Downtown is evolving. The Jets are back. The Moose are back. A new police headquarters is opening around the corner.
“I’m taking the menu through a mix of the deli and a lot of other things that I’ve either made up myself or learned along the way, and have cross-mixed Jewish cuisine with deli and Mediterranean cuisines. A lot of things on the dinner menu are ones I grew up with at home.
“A lot of the menu is made in mind with our Winnipeg winter. A lot of the menu was made in such a way to cater to  people like police who will be working around the clock in the cold, and hopefully we’ll see them as fixed staples, not just in the day time but evening-time too.
“With everything being made from scratch, everybody is adjusting to the new menu and the longer hours. I’m a little bit too ambitious still and have energy. We want to have a presence and compete, and be the best at it.”
On your next visit to Oscar’s, you might want to try their matzo ball poutine or their dirty burger.
Although the deli is not kosher, both Haidau and Brown are working to provide more service to the Jewish community, as they offer a wide variety of catering options for all occasions.
“We have a beautiful patio as well that we renovated this summer that can accommodate functions,” said Haidau. “We did a Christmas party here last night with a pop-up bar for the Park Theater.”
Oscar’s Deli is open from 7am-to-7pm, Monday to Friday, and before Jets games. “If dinner goes, who says we won’t be able to push it until 9:00 pm?” wondered Haidau. “But, I don’t think our intent is to be like a Boston Pizza lounge for after the game. I want to have kids and be able to be there for them somewhat too.”