The Wise Guy

The Wise Guy is a Crossroads Italian-American tavern at 1924 Main Street, opened in April 2024 by Rockhill Restaurant Group co-owners Bret Springs and Zach Marten in the historic former Rieger Hotel building, serving Chicago-style thin-crust tavern pizza, pastas, Italian sandwiches, and salads.

Description

The Wise Guy is an Italian-American tavern in the Crossroads Arts District, designed to evoke the kind of old-school Italian taverns associated with New York and Chicago. The interior leans into a “Second City” atmosphere — dimly lit, with dark wood, red leather banquettes, and wall-mounted TVs that blend upscale-casual dining with sports-bar elements.

The menu centers on Chicago-style thin-and-crisp tavern pizza alongside Italian appetizers, pastas, chopped/Italian salads, and Italian sandwiches. Documented items include bruschetta, garlic knots, carbonara deviled eggs, chicken parmesan, spaghetti and meatballs, carbonara, and a fried-parmesan chicken sandwich.¹² A happy-hour program has been advertised with discounted pizzas, house cocktails, and beer.³

The restaurant occupies 1924 Main Street, the ground floor of the historic former Rieger Hotel building. The “Wise Guy” name is a nod to Prohibition-era gangsters — including Al Capone — said to have stayed at the Rieger Hotel; the owners deliberately preserved historic building details such as the original tile work and light fixtures.⁴²

Ownership and history

The Wise Guy is owned by Bret Springs and Zach Marten, the co-owners of Kansas City’s Rockhill Restaurant Group.¹⁴ The group also operates Rockhill Grille (two locations) and the owners hold additional Kansas City hospitality interests, including partnerships connected to Joe’s Kansas City Bar-B-Que and County Road Ice House in the Power & Light District, as well as the local license for the holiday-themed Miracle pop-up bar.¹²

Springs and Marten had reportedly wanted to open a pizza-and-pasta concept since closing Coal Vines on the Country Club Plaza in 2017, and The Wise Guy is the realization of that idea.²

The restaurant opened in April 2024 at 1924 Main Street, a space that had operated for roughly 16 years as a fine-dining establishment within the Rieger Hotel building before the hotel closed during the COVID-19 pandemic (in 2020) and the storefront sat vacant.¹²⁴

Menu

Last verified: 2026-06-23 · Source: The Wise Guy official online menu (via thewiseguykc.com → LingoEats menu host) and Toast pickup-ordering menu, corroborated by The Pitch and Kansas City Magazine dining coverage · Confidence: Medium (item/category structure and representative prices verified across multiple sources; the JavaScript-gated official menu host and Toast page could not be scraped in full, so the line-item list below is representative rather than exhaustive).

Pizza style: Chicago-style thin-and-crisp tavern pizza — confirmed across official listing copy and press coverage (not deep-dish; the round, cracker-thin tavern style).⁵¹⁶ House hot honey (Italian-leaning, with rosemary and thyme) is provided tableside in caddies alongside red pepper flakes and parmesan.⁶

Pizza

• Cheese Pizza — with choice of toppings ($16).⁵
• Spicy Italian Sausage & Housemade Giardiniera — a signature tavern pie ($20).⁵
• House Special — multi-meat pizza (signature).⁵
• Margherita and Pepperoni also offered.⁵ Pizzas generally run $16–$25.¹⁵

Appetizers

• Garlic Knots ($12).⁶
• Bruschetta ($14).⁶
• Housemade Mozzarella Sticks — parmesan and crispy-prosciutto crust, marinara, fig-marsala sauce ($11).⁵
• Carbonara Deviled Eggs.⁵
• Calamari — with shrimp, zucchini, mushrooms, broccolini, marinara ($16).⁵

Salads

• Caesar — baby romaine, focaccia croutons, parmesan ($12).⁵
• Burrata / Caprese and a chopped Italian salad round out three salads, $12–$16.⁵¹

Pasta (four options, $19–$25)

• Spicy Rigatoni alla Vodka.⁵
• Spaghetti & Meatballs, Carbonara, and Chicken Parmesan (breaded cutlet, marinara, mozzarella, choice of pasta — $23).⁵¹

Italian sandwiches (four, with a side, $14–$18)

• Pesto Chicken Panini — grilled chicken breast, fresh mozzarella, arugula, preserved tomato, pistachio-basil pesto, Balsamela on focaccia ($15); served with Calabrian-chili aioli and house-made potato chips.⁶
• Additional subs/sandwiches offered on focaccia or Rustic Italian baguette.⁶

Entrees & desserts

• Three specialty entrees, $23–$34 (including shrimp scampi).¹⁵
• Desserts: Limoncello-Pistachio Cake, Tiramisu Cannolis.⁶

Lunch (Fri–Sun): a quarter pizza paired with choice of pasta salad, caprese, or Caesar for $15.¹ Prices are representative and subject to change; verified 2026-06-23.

Links

• Website: https://www.thewiseguykc.com
• Instagram: https://www.instagram.com/thewiseguykc/
• Phone: (816) 326-7300

See also

• crossroads-arts-district
• Registry

Sources

Footnotes

1. Kansas City Magazine, “There’s A New Italian Spot In Town.” https://kansascitymag.com/theres-a-new-italian-spot-in-town/ — accessed 2026-05-30. ↩ ↩² ↩³ ↩⁴ ↩⁵ ↩⁶ ↩⁷ ↩⁸ ↩⁹ ↩¹⁰

2. FOX4 KC, “New restaurant moving into Rieger Hotel building in Kansas City.” https://fox4kc.com/business/new-restaurant-moving-into-rieger-hotel-building-in-kansas-city/ — accessed 2026-05-30. ↩ ↩² ↩³ ↩⁴ ↩⁵

3. IN Kansas City Magazine, dining-guide listing — The Wise Guy. https://www.inkansascity.com/eat-drink/dining-guide/the-wise-guy/ — accessed 2026-05-30 (page returned HTTP 403 on direct fetch; details corroborated via search excerpt). ↩

4. KC Daily, “Who’s The Wise Guy?” https://www.kcdaily.com/p/whos-wise-guy — accessed 2026-05-30. ↩ ↩² ↩³

5. The Wise Guy — official online menu (thewiseguykc.com/menus redirects to LingoEats menu host) and Toast pickup-ordering menu. https://www.thewiseguykc.com/menus → https://lingoeats.com/m/675d4d3f-f47c-4b6c-a259-d055d2587be6; https://www.toasttab.com/local/order/the-wise-guy/r-c3e74e8c-7fd3-4b60-90aa-7d0b3793a41b — accessed 2026-06-23. Asserts: Chicago-style thin-and-crisp tavern pizza style; cheese pizza ($16), spicy sausage & giardiniera pizza ($20), house special, margherita, pepperoni; mozzarella sticks ($11), carbonara deviled eggs, calamari ($16); Caesar salad ($12) and chopped/burrata salads ($12–$16); spicy rigatoni alla vodka, chicken parmesan ($23) and four pastas ($19–$25); shrimp scampi and entrees ($23–$34). (Official menu host and Toast page are JavaScript-gated/HTTP 403 on direct fetch; line items corroborated via search excerpts and the press sources below.) ↩ ↩² ↩³ ↩⁴ ↩⁵ ↩⁶ ↩⁷ ↩⁸ ↩⁹ ↩¹⁰ ↩¹¹ ↩¹² ↩¹³ ↩¹⁴

6. The Pitch, “Dish & Drink KC: Unexpected versatility at The Wise Guy and Kate Smith Soirée.” https://www.thepitchkc.com/dish-drink-kc-unexpected-versatility-at-the-wise-guy-and-kate-smith-soiree/ — accessed 2026-06-23. Asserts: garlic knots ($12), bruschetta ($14), pesto chicken panini ($15) with Calabrian-chili aioli and house chips, focaccia/Rustic Italian baguette breads, house Italian hot honey (rosemary/thyme) in table caddies, desserts (Limoncello-Pistachio Cake, Tiramisu Cannolis). ↩ ↩² ↩³ ↩⁴ ↩⁵ ↩⁶ ↩⁷