The Face of the Bayside: Remembering Smilen Bob MacDonald

Door County has lost one of its worst bartenders. Well, maybe worst isn’t right. For sure Bob MacDonald wasn’t the fastest drink slinger in town, nor was he always great at remembering your order, but for years he was the guy you went to see at the Bayside Tavern in Fish Creek.

“He wasn’t the best bartender in the world because he loved to talk to his customers so much,” said his daughter Christie Weber. “The joke back then was that you had to go to the payphone and call the Bayside so he would have to answer. Then you could order your drink.”

MacDonald died March 29 at age 90.

His children said they didn’t know the gregarious, social side of their father until he bought the Bayside with his wife, Elaine, in 1975. That’s when he stepped behind the bar and became the man known simply as Smilen Bob.

MacDonald was born Sept. 29, 1928, in Sturgeon Bay, and in 1951, he eloped with Elaine Sellissen. The young couple made their home on the west side of Green Bay, where they raised six children he was fiercely proud of: Pat, Christie, Bob, Ron, Billy and Karen. Shortly before their annual summer camping vacation at Peninsula State Park in 1975, MacDonald lost his job at Procter & Gamble, but the timing proved fortuitous.

On that vacation, they stumbled into a conversation with Ray and Millie Wolter, then the owners of the Bayside – a shot and beer bar they were looking to sell. By mid-August, Bob and Elaine were the new owners, but there were a couple of problems with their new plan: Elaine and Bob weren’t tavern-goers, and they had never worked in the service industry.

“His first day, a customer ordered a rum and Coke, and my Dad turned to me and asked, ‘How do you make a rum and Coke?’” recalled Weber, who was 19 at the time and already enlisted in the family business.

But Bob’s newly unleashed personality made up for his lack of bartending skills. He took to being the face of the bar while Elaine took care of the business and the cottages. Smilen loved his regulars who talked about cars, education and the rumor mill, and he wasn’t afraid to break tavern norms by striking up a political conversation.

Smilen Bob MacDonald

“He didn’t care about your background,” Bob Jr. said. “He treated everybody the same – if you were the guy with the big yacht in the harbor or the deck hand.”

“Smilen was the main attraction,” said longtime friend Digger DeGroot. “He was a character, like the Kramer – the character from Seinfeld – of Fish Creek because you never knew what goofy thing he was going to do.”

His favorite phrase was simple and sounded a lot like “dippy spit.” Everyone who knew him was called it at one point or another. And when the sun went down, he was famous for his dance, called “The Smilen”: chin and elbows up, butt and chest out.

But bar life wasn’t easy on the family. At one point, the entire clan lived in the tight quarters of the bar, and by 1980, after 29 years of marriage, Smilen and Elaine divorced. In most tales, this would be where the story ends – another short-lived tavern flame-out – but the Bayside and the MacDonalds weren’t like most stories.

Smilen Bob MacDonald bought the Bayside Tavern with his then-wife Elaine in 1975. The couple turned it into a Door County institution. Submitted.

“We argued less after the divorce than when we were married,” Elaine said. “When we were getting the divorce, we’d go to lunch before seeing the lawyers. When it was final, Bob was sad and asked, ‘Does this mean we don’t get to have lunch anymore?’ I guess we were just always friends.”

So they continued to run the tavern together – Smilen out front as the ambassador, and Elaine running the books and managing the cottages that later became shops. “My mom was the boss, the brains behind the operation, and they didn’t question each other,” Bob Jr. said. In the afternoons, they’d both be at the bar – Elaine in her seat in the corner, and Smilen three stools down around the corner.

“People always thought we had such a great marriage,” Elaine said. “Some of our customers came here for years before they knew we were divorced.”

Eventually they’d each take a boyfriend or girlfriend to the bar, all four of them hanging out a few seats from each other at the Bayside happy hour – one of the few places where such an arrangement could be normal.

They were married for 29 years and divorced business partners for 39. “We still had a lot of love for each other,” Elaine said. “And we both loved this place. It has a lot of soul.”

Oh, and where’d that nickname come from? That’s credited to Rick Hollister, an old friend who once said, “Every time the till opened, he had a big smile on his face.”

The MacDonald clan at the 25th-anniversary party for the Bayside Tavern. (From left) Bob Jr., Christie, Karen, Elaine, Bob Sr., Pat and Ron. The late Billy MacDonald is not pictured. Submitted.