In this series, we’ll be hiking the burger trail to find the latest, greatest and most delicious burgers in Milwaukee. Click here for an explanation of the criteria used to rate each burger. Where have we been? Check out the complete catalog of burger reviews here.
Oscar’s Winner’s Circle
3800 W. Burnham St.
(414) 249-5701
facebook.com/oscarswinnerscircle
Oscar’s Winner’s Circle, the sister restaurant to Oscar’s on Pierce, opened last spring. Despite its former life as a corner tavern, the new location is bright and cheerful with plenty of windows, comfortable seating and a warm wood-filled interior that’s modern, yet cozy.
While the menu is thematically similar to the Pierce Street location, the signature burger offerings are quite different. A few are inspired by classic Mexican flavors (The Gordo features chicharrons, salsa verde and chihuahua cheese), while others are more internationally focused (take the banh mi burger, for instance).
On my latest visit, I ordered up a Winner’s Burger which features a laundry list of toppings including ham, bacon, chorizo, peppers, fried onions, chipotle jack, and a mix of fresh onions and cilantro. It comes with a side of guacamole and hand-cut fries ($8.25).
Presentation: 8
This burger is impressive. It looks huge on the plate with its big, majestic bun. There’s not a ton of color at play with this one, though in my case you could see the peppers and fried onions gliding right over the edge of the burger along with bits of melted cheese. There was a certain greasy charm about it, and the small wafting up from the plate was pretty fantastic.
Bread/bun: 8
Like the buns at Oscar’s on Pierce, these are light and airy with just a bit of chew. And, despite the bun’s appearance as being far too overwhelming for the burger, it’s that airiness that redeems it. The bun, which was also nicely toasted, has capacity for soaking up a good bit of the juices from the burger. And that’s a very good thing. After all, in this burger’s case, the juices are mingled with the flavors of bacon and chorizo, and you don’t want to lose a single bit of them.
Burger: 8
I didn’t really distinguish a difference between the burger at this location and the original Oscar’s. In fact, the kitchen seems to be prepping them in an identical fashion. After all, when I ordered mine mid-rare, it came closer to medium and that’s very consistent with my experience at both spots. Even so, the loosely packed burger was still juicy, with just enough fat to give it a nice unctuousness. It was also well seasoned, with a nice beefy flavor.
Toppings: 8
Combined, the toppings on this burger offer a nice spectrum of flavor: salty, pickled, fresh and spicy. Both the ham and bacon are chopped, so their presence doesn’t overwhelm the burger, but there’s a little bit of porky flavor in every bite. Raw onions supply a bit of texture, and the chorizo enriches the burger with a bit of its greasy, spicy goodness. It’s not overly cheesy, but there’s enough chipotle jack to supply that fatty, gooey umami you want on any burger. Definitely add the guacamole to the burger; it’s a nice fresh element on a burger that’s otherwise pretty meat-forward.
Value: 10
If Oscar’s has one thing in the bag, it’s value. You get a hefty burger with big flavor and a healthy portion of hand-cut fries for just over $8. No arguments here.
Total: 42/50
If you like the burgers from Oscar’s on Pierce, you’ll likely find another happy place at Oscar’s Winner’s Circle.
Oscar’s Winner’s Circle is open daily from 11 a.m. to 11 p.m.
As a passionate champion of the local dining scene, Lori has reimagined the restaurant critic's role into that of a trusted dining concierge, guiding food lovers to delightful culinary discoveries and memorable experiences.
Lori is an avid cook whose accrual of condiments and spices is rivaled only by her cookbook collection. Her passion for the culinary industry was birthed while balancing A&W root beer mugs as a teenage carhop, fed by insatiable curiosity and fueled by the people whose stories entwine with every dish. Lori is the author of two books: the "Wisconsin Field to Fork" cookbook and "Milwaukee Food". Her work has garnered journalism awards from entities including the Milwaukee Press Club. In 2024, Lori was honored with a "Top 20 Women in Hospitality to Watch" award by the Wisconsin Restaurant Association.
When she’s not eating, photographing food, writing or planning for TV and radio spots, you’ll find Lori seeking out adventures with her husband Paul, traveling, cooking, reading, learning, snuggling with her cats and looking for ways to make a difference.