It’s easier to get a hold of Jerry’s Pizza these days than it used to be. That doesn’t mean it’s raining pies, though.

Jerry Benedetto—who developed an 18-month waiting list for his thin-crust Chicago tavern style pizza while making them in his home kitchen while in quarantine—is now operating out of the tiny kitchen at the Bear Paw Inn, near the Aladdin Theater. But it’s still a one-man operation. And don’t expect to roll up and order at the bar: Jerry’s holds a ticketed sale once a week. On a recent drop, 30,000 hopefuls crashed his restaurant’s website, all hoping to get one of the 25-30 pizzas Benedetto is able to put out each of the four nights he’s open.

“I just laughed,” Benedetto says. “I honestly felt bad, like I wasted their time.”

The scarcity isn’t to build hype. Rather, Benedetto says he’s taking it slow. The Chicago native doesn’t have a background in the restaurant industry—he taught himself to make what he calls “the real pizza” of the Windy City at the start of the pandemic because it didn’t exist in Portland.

The pizzas struck a nerve, and what started as a passion project expanded into online sales via Instagram, initially to friends, then strangers. Benedetto spent a few months figuring out how to recreate the square cut pies in a commercial kitchen, and opened at the Bear Paw Inn in mid-May.

“It’s still just Jerry,” he says, smiling underneath what’s become his signature thick mustache and ubiquitous Chicago sports- team wear (In this case, Bears hat and White Sox jacket.) “I’ve got a pizza in the oven as I’m making a pizza, while delivering a pizza to a table. It’s definitely not sustainable.”

The draw for many of his customers is the taste of home, but even those who didn’t eat Chicago pizza growing up still find something nostalgic about it: The thin crust, the slightly sweet sauce, the salty pepperoni and fennel-tinged sausage evoke a powerful pizza memory even for this native Oregonian. I’m about to tell Benedetto what his pizza tastes like to me, but before I even get the chance, he says it himself: “It’s a quality Totinos.”

Sometime soon, Benedetto says he plans to hire help, and when he’s ready, he’ll open a spot of his own. But while Benedetto is the first to joke that “it’s just pizza,” know that he’s also deadly serious about making sure the pies stay perfect as he scales up, and he refuses to go faster just to capitalize on the buzz. As a newcomer to the food world, starting at the Bear Paw provides little to no risk and a chance to make mistakes, before spending the hundreds of thousands of dollars it can take to open a restaurant, he says.

Benedetto’s goal is to have a place “like fuckin’ Cheers,” where families can come after kids’ sports games, drinks are served in those red plastic cups every pizza joint had in the ’90s, and there’s pizza and buckets of spaghetti and meatballs on demand.

“My ultimate goal is pizza, but it’s so much more than pizza,” Benedetto says. “I love watching strangers talk. I see people share pizzas. I want to bring people from all different backgrounds together into a space.”

So what, exactly, goes into the upscaled Totino’s? We had Benedetto breakdown the audience favorite: the Jerry’s Special.


Breakdown: The Jerry’s Special ($26)

The cornmeal: Under each pizza is what Benedetto calls a “fuck ton” of cornmeal. While it’s usually used in a lesser amount to slide the pizza off the peel into the oven, Benedetto says he uses more, as it adds flavor and texture. He also says it’s fun—he’s watched patrons draw doodles in the yellow grains and then lick their fingers.

The dough: It’s a two-day process to get the thin crust just right. Handmade with all purpose flour, it rests overnight, rises for an hour at room temperature, and then goes into the cooler for one night. “Ratios are critical, especially when you’re making a thin crust,” Benedetto says. “It’s a vehicle to get sauce, cheese and toppings to your pie hole. It has to hold them.”

The sauce: It’s the sauce that really ties a Jerry’s pizza together. Bright and fresh with a touch of sweetness, it’s a riff on his Grandma Pat’s pasta sauce recipe. Canned whole tomatoes and romano and parmesan cheeses are involved, and that’s all he’ll say.

The cheese: Wisconsin mozzarella and a touch of parmesan at the end. ‘Nough said.\

The pepperoni: 51 mm old-world slices (not cups) from Ezzo Sausage Company in Columbus, Ohio.

The sausage: Benedetto makes it by hand, using ground pork, fennel and oregano, and he uses a method of pinching and pulling the sausage with one hand to get just the right amount on each pie. Benedetto also pushes each piece into the crust, so as the pizza bakes, the fat renders into the crust and sauce for even more flavor.

The mushrooms: They’re canned, and Benedetto is proud of it. He says they add a spongy texture while fresh mushrooms tend to dry out.

The bag: If you order to go, Jerry’s pies are sent away in a paper bag instead of a pizza box, which he says is the more traditional and authentic way these tavern style pizzas are served.

EAT: Jerry’s Pizza at Bear Paw Inn, 3237 SE Milwaukie Ave., 4-9 pm Monday-Thursday, preorder only.