Welcome to Jerry's, the Midwest bar in the heart of Ducks country

The man known for his pizza has built something better.

Tyson Alger/I-5 Corridor

PORTLAND — I’ve known Jerry Benedetto for about two minutes and I’ve already messed up.

I came down to Jerry’s Tavern here in Portland’s Northwest industrial district on Tuesday to write a story for this weekend’s Ducks game. Oregon is playing Wisconsin in Madison and I’ve been waiting the entire year to pull out the Jerry’s card: The bar has been one of my favorites to visit since its opening earlier this year, largely due to its Midwestern hospitality and really good chicken wings.

Memorabilia from the Bears, Bucks, Badgers, Packers, Brewers, Cubs and Blackhawks blanket the walls. An ‘Old Style’ sign adorns the entrance on N.W. Nicolai St., just down the hill from the Montgomery Park building. Beers are cheap. The food is good (and cheap). And its mustachioed namesake makes his presence felt everywhere, whether he’s greeting regulars at the door, grabbing Miller High Lifes or providing tableside Malort shots.

It’s 2:02 p.m., the bar opens at 3 and I just explained to Jerry my outline: It’s the Ducks. It’s the Badgers. The Big Ten move had to be great for business for a Midwest-themed bar in Oregon.

He winced.

“Don’t take this the wrong way,” he says, “but this is where I’m from. It’s not schtick or a theme, it’s just, this is all my shit. This is just what a bar is like from where I’m from.”

Jerry, 37, is from Northwest Illinois. He’s married to Lauren, who is from Wisconsin. The two moved to Portland from Milwaukee in 2019 when Lauren got a job at Nike, and for the last few years Jerry has alternatively longed for the tavern-style bars that littered corners of blocks where he grew up in Freeport, while also planning his life-long dream of creating his own place.

Jerry’s opened its doors in May. And while he’s not technically open now, a couple of men just walked in, took a seat at the bar and started watching SportsCenter. Jerry tells them the kitchen doesn’t open for another 45 minutes, but he can grab them a beer.

“Friendly. Friendly. Friendly,” Jerry tells me is the chief principle of the bar. “Acknowledge. Acknowledge. Acknowledge. Why do people come here? Because we say hello and we know your drink.”

So, we should probably talk about the pizza thing. If you haven’t been to Jerry’s, but for some reason his name — or face — looks familiar, it’s because there was a spell here in Portland where he accidentally built himself a bit of a pizza empire. Long story short, Jerry started making thin-crust pizzas at home to cure boredom during the pandemic. He made some pizzas for friends, who told their friends, who told their friends and, before he knew it, Jerry had himself an 18-month waiting list and was being hailed by The Oregonian as a “pizza king” as he transitioned his business from his kitchen to a pop-up in the back of Bear Paw Inn.

He amassed quite an Instagram following, too. And when his pop-up ended in 2022 and he transitioned all his effort into opening Jerry’s, the masses grew impatient waiting for their next slice.

But here’s the thing: Jerry’s has been open for nearly seven months and pizza remains off the menu. At first, it was a hardware issue: Jerry needed a new pizza oven. But then it became something else. See, Jerry’s isn’t big. Fire Code has the bar around 50 people, which creates a cozy and social atmosphere. He gets neighborhood regulars who finish their shifts and saddle up. It gets crowded when the Bears are on. It gets crowded when the Packers are on. It becomes downright mayhem when the Bears and the Packers are on.

While he hasn’t been in Portland for long, he did get a good taste of what becoming the pizza du jour in this city can do to a business. And, frankly, Jerry tells me he just doesn’t think he can pull it off.

“The thing about being a small bar is you’re almost forced to not being an asshole,” he says. “When it gets crowded you’re so close to everyone else that you can’t be an asshole. It wasn’t by design, but it’s small enough that you get a lot of, ‘Oh wait you’re from Mukwonago? Holy smokes, I grew up in wherever.’ You get that a lot with a lot of the Midwesterners that come through here.

“I have this fear that if I start doing pizza it’ll start pushing out some of those people that have kept the lights on. Like, Don over here can’t get a seat anymore because now there’s pizza. If I could have done this all over again I would have gone a little bigger. I would have gotten help. But at the same time, the reason why we’re doing ok right now is we’re small.”

Jerry says it doesn’t help, either, that he’s dealing with a fair amount of imposter syndrome. Jerry’s never owned a tavern — he’s got a background in sales — and repeatedly says he doesn’t know what he’s doing. He tells me the pizza was never all that great, and the wings, the ones that drew me in and have recently garnered their own share of accolades, are just “fried for a really long time so they get a little crispy and then we toss them with Frank’s and butter. That’s it.”

“Turns out, I don’t think I’m very good at this,” Jerry says. “And to do the volume that we would need to do for pizza, I’d need help. And I think it’s more than the pizza. It’s about making people feel a certain way.

“Truly, the pizza is just OK.”

He dreams of being bigger. He’s talked with a friend about potentially opening a separate pizza place. But he’s also frightened of messing up what he has, which now, 15 minutes before opening, is a tavern where every barstool is occupied after the guys at the bar slid down to make room for a group at a table that wanted to chat.

He says he’s not packed every night. And while he also says he’s not a sports bar¹, he says football season coming around has been a big boost. Jerry’s is the official watch party destination of the Wisconsin Alumni Portland Chapter, and Saturday’s 4:30 p.m. kickoff will feature a bar packed full of Badger Red.

But there will also be a handful of Oregon Ducks jerseys. And that’s OK, Jerry says, because that’s a part of who he is now, too.

“It’s [easy to put Oregon games on], and I live here now,” he says. “But if there’s 60 people here all wearing Ducks jerseys, yeah, it might get a little uncomfortable.”

— Tyson Alger, The I-5 Corridor

1. “Portland doesn’t do sports bars well. This wasn’t even supposed to be a sports bar. I opened this as a small bar that has TVs, but apparently, if you have TVs in this town you’re a sports bar.”