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About Us.

Tough Luck is the third bar from the folks behind The Old Gold, the long-running North Portland bar with a well-received whiskey problem, and Paydirt, the dedicated drinking establishment in the Zipper Building on NE 28th and Sandy Blvd.

Situated in the Woodlawn neighborhood and housed in a mid-century building (formerly the 18th St. Market) that is still to this day owned by the family of famed African-American developer Arthur Palmer. Tough Luck was slowly rebuilt while maintaining the integrity of the ’60s-era structure. But long before shovel hit dirt, Tough Luck’s local lineage was already established: Co-owner and bar manager Andrew Finkelman is the grandson of Portland natives, and his home sits on the very tree-lined block where his mother was born, a few blocks away from where Tough Luck sits today.

With that established foundation, Tough Luck aims to provide Woodlawn with a bastion of booze and creative food. Long before chef Lauren Miller cut her teeth in the kitchen of Imperial alongside Doug Adams and Vitaly Paley, she learned under the tutelage of a far more demanding chef: her grandmother. Raised in a small Kentucky town, Miller’s grandmother passed along a treasure trove of deep-rooted Southern recipes, all of which used a chipped teacup for a measuring spoon. Miller’s modern influences pull from the Far East, which gives Tough Luck’s menu a unique balance of food from both Korea and Kentucky. Diners can look forward to dishes like Korean Fried Chicken (with rice, avocado, banchan, and tom kha sauce) and a house burger (with crispy double patty, pimento, kimchi ketchup, shaved iceberg, soy pickles, and Pearl Bakery bun).

The roots of Tough Luck’s bar program run just as deep. Finkelman stirred his first Old Fashioned in 1973. He was nine years old. Cocktails at Tough Luck will be playful and informal, including mix-and-match whiskey/beer pairings, a dedicated menu of Old Fashioneds, a line of house-made shrubs, and ten constantly rotating beers on draft. In addition, a wrap-around exterior patio, and a restored 1940s 22-foot shuffleboard table, complete with a custom-made electric 16-foot scoreboard, will keep indoor patrons entertained.

And that is Tough Luck. 

Why the name "Tough Luck"? It took well over a year of demolition, plus many more additional months, to open our doors. There were setbacks, mishaps, construction disasters both large and small, and when it came time to decide a name, it only seemed fitting.

We opened in May of 2017. Please come by and say hello. We’re happy to be where we belong.