Winky Dinky Dogs opens in Oakland's former Original Kasper's triangle

""It's been a long process, but we're finally open, and the community has embraced us," Allen said. "We've been pushing a thousand hot dogs a day, even right now as we speak." Allen is known in the community as being part of the legendary hip-hop group The Digital Underground. His second career as a restaurateur appears to be taking off. Aside from his Winkies, in late 2025 he also opened the Bread Winners sandwich shop in Oakland's Swan's Market."

"The eatery has moved into a building that fittingly has a tubular past. Since the 1940s, it was home to Original Kasper's Hot Dogs, a local institution that moved out in 2003. The triangle-shaped structure, which viewed from above looks like a pizza slice, attracted graffiti and even an art show devoted to its ever-changing facade before Allen bought it in 2025."

Winky Dinky Dogs opened Jan. 24 at Telegraph Avenue and 46th Street in Oakland's Temescal neighborhood, occupying a triangle-shaped building once home to Original Kasper's Hot Dogs. Owner Tyranny Allen, a former member of The Digital Underground and local entrepreneur, operates multiple Oakland businesses including Bread Winners. Winky Dinky's menu includes beef, chicken, pork and vegan dogs, a chili dog and specialty items, plus fried ribs, gumbo and "wangs." The location sells high volumes—about a thousand hot dogs daily—and continues Allen's roots in street-cart hot-dog vending.

Read at The Mercury News