Still Smiling on the Inside: Remembering Delmar “Pickle” Olson

There are few things that get under a restaurant server’s craw more than the customer who walks in five minutes before you’re supposed to open. You may have been banking on those last five minutes to finish your setup for service, but you can’t just push those early birds out the door, and you can’t ignore them. You have to – grudgingly – take care of them. 

An early, demanding customer might set you back – and set the tone – for the entire day. It did for Delmar “Pickle” Olson at Husby’s back in 2000, when we had one customer who made a habit of coming in a few minutes before the opening bell every week. I’d be prepping in the kitchen, and the legendary duo of Pickle and Kim Tank would be rushing to set up the bar (OK, Kim would be rushing, and Pickle would be… Pickling). Then this older gentleman and his wife would come in the back door, mosey into the dining room and squeeze themselves into a booth. 

One day, this led to the greatest customer interaction I’ve ever heard. 

Pickle slid an ashtray onto the table as he waddled by and asked, “How are you today?”

The older man replied with gusto, “Well, I’m still alive!”

Pickle, without missing a beat or breaking “stride” in his waddle, replied, “Well, that’s too bad.”

He wasn’t joking, he didn’t wink and he didn’t smile. He just walked on to toss the next ashtray onto the next table. Pickle, who died April 5 at age 77, was dry like that – deadpan – and hilarious if you got to know him. Once asked why he didn’t smile more, he replied, “I’m smiling on the inside.”

By the time I met him Pickle was approaching his 25th year behind the bar at Husby’s. He spent almost 13 of those as the owner, from 1978 to 1991, back when Husby’s was a dive – about half the size of the current incarnation, and when part of the gig was fielding phone calls from wives tracking down their husbands whose “stop for a beer” became several. He didn’t have the looks or the charm of Sam Malone, but he did love his sports, his baseball and shooting the breeze through a happy hour.

By the time I got there, Pickle had long since become a daytime guy, in at 10 am and out at 6 pm, well before things got rowdy. When he arrived for work I was, often, hungover. Some days I was more so, and he could spot the bad ones coming from across the parking lot. Few people could say so much with so few words. 

Pickle would walk in the back door and up the ramp, turn the corner – where he could see me pouring my fourth cup of crappy coffee into the brown mugs that populated half the restaurants in America at that time – and stop dead in his tracks (not hard for Pickle – he was never moving all that fast). 

He’d make a sound – “Pfft” – and shake his head slowly. “I guess there ain’t gonna be a special today?”

Pickle had been there. You don’t own a dive bar like the old Husby’s without plenty of mornings like that. 

You also don’t own a bar like that without knowing the history of the people there, the deep-set animosities, the grudges, the backstories. The good and the bad. Pickle knew where all the bodies were buried, and he made sure only the tight-lipped learned the secrets. 

He was born in Chicagoland, and though his family migrated north before he was two and he would graduate from Gibraltar High School, he remained a White Sox and Bears fan behind the corner bar in Packers country. He got a few years in the ’80s to stick it to his patrons, but he spent most of his time in the misery of Bears fandom and he took it in stride. 

Pickle did embrace three Wisconsin teams: the Badgers, the Gibraltar Vikings and the Sister Bay Bays of Door County League baseball. For the Bays he played 15 years well enough to be inducted into the league’s Hall of Fame in 2004. 

In a stroke of irony, he and his wife, Terry, whom he met when she was a waitress across the street at the Sister Bay Bowl, bought a home built in the 1930s that was once owned by another legend, Emma Husby: the woman who gave his bar its name. 

Pickle’s nickname was formulated in the way so many classic small-town nicknames catch on. It started with his first name, Delmar. That got shortened to Del, which sounds like Dill, which of course leads to Dill Pickle. Which becomes, simply, Pickle, shortened by his friends to Pik. And once it was slapped on, it was hard to call him anything else. 

Like Weasel, and Two-beer, and Psycho, and Juice. Tugboat. Johnny G. Torch. Jikes. Little Eddie. Big Eddie. Big Mike. 

People you know for years without ever knowing their real names. And don’t need to. 

Pickle was a one-name man. Sort of like Madonna, or Pelé. Maybe more like Ditka. 

But he was better. He was part of the soul of a place, whether he was smiling inside or out.