Winstead's

Winstead's is a regional hamburger restaurant chain associated with Kansas City, Missouri, and the broader Kansas City metropolitan area. Its roots reach back to 1936, when Kathryn Winstead established Winstead's Drive-In in Springfield, Illinois. The early format was a classic American drive-in: customers parked in designated stalls, signaled with their vehicle lights, and received service from carhops. Related Winstead family operations subsequently appeared in Jacksonville, Illinois, Fort Wayne, Indiana, and Sedalia, Missouri. The Sedalia operation, opened by members of the family in 1937, was described as the first drive-in restaurant west of the Mississippi River. The brand's defining Kansas City location opened in 1940 near the Country Club Plaza, at the intersection of 47th and Main streets. Kathryn Winstead and her sister Nellie Winstead moved ahead with the project despite the commercial and political complexities of developing property in Kansas City at the time. Unlike a purely car-oriented drive-in, the Kansas City restaurant accommodated indoor customers as well as motorists. Its Streamline Moderne, later commonly described as Art Deco-inspired, design became central to the brand's identity. Winstead's restaurants are recognizable for their prominent exterior towers and visual association with mid-century roadside dining. The business faced supply pressures during the Second World War, particularly because beef rationing affected its core menu. It expanded after the war and eventually acquired the property occupied by the original Kansas City restaurant. Under Nellie Winstead and her husband, Gordon Montgomery, the menu later broadened beyond burgers; french fries and milkshakes were added in 1957. Oversized “skyscraper” sodas and milkshakes, intended to serve several people, became among the chain's most distinctive offerings. Kathryn Winstead retired from the restaurant business in 1952, leaving operational control to the Montgomerys. After her death in 1967, the Montgomerys sold the restaurant two years later to Morris and Victor Lerner, Kansas City businessmen associated with King Louie International, a bowling-entertainment and apparel company. The Lerners expanded the chain with locations in Kansas City North and Overland Park, Kansas. In 1982, King Louie International was sold to an investment group, which considered closing or divesting the relatively small restaurant operation. Local restaurateur Nabil Haddad, described in reference material as a McDonald's franchisee and major McDonald's shareholder, ultimately became the operator associated with Winstead's. The brand is owned by Haddad Restaurant Group. Winstead's has remained a regional rather than national chain. At various points it operated several restaurants in the Kansas City area, although locations have been closed over time, including restaurants in Overland Park and Lenexa. Its reputation rests on continuity: griddled hamburgers and cheeseburgers, simple sides, shakes and large-format drinks, together with the architectural character of its original restaurant. Food Network Magazine recognized Winstead's as having the best hamburger in Kansas, while food critic Calvin Trillin has praised its cheeseburgers in especially strong terms. In 2020, the business filed for Chapter 11 bankruptcy protection and reported more than $1.5 million in debt. Available reference material continues to identify Winstead's as an operating brand under Haddad Restaurant Group, but a complete current store list and detailed post-bankruptcy corporate information are not established here.

Winstead's originated in the Winstead family's drive-in restaurant activities in the American Midwest. Kathryn Winstead founded Winstead's Drive-In in Springfield, Illinois, in 1936. The concept was among the early U.S. drive-in formats, with customers parking in stalls and signaling carhops by flashing their headlights. Around 1938, Kathryn's brother Jack opened another restaurant in Jacksonville, Illinois, while another sister established a location in Fort Wayne, Indiana. The family's Missouri connection was strengthened after Fannie Winstead Garst moved from Sedalia to Springfield following the death of her husband, Jesse D. Garst. Fannie assisted her sisters in operating the Springfield business, and the family later sought to return to Missouri. In July 1937, members of the family opened Garst's Drive-In in Sedalia. That restaurant has been characterized in the reference material as the first drive-in west of the Mississippi River. Kathryn and Nellie Winstead later pursued a Kansas City location near the Country Club Plaza. The Kansas City restaurant opened in 1940 near 47th and Main streets. Its design differed from a basic carhop stand by providing both indoor and outdoor service, and its Streamline Moderne appearance established the architectural style that would become inseparable from Winstead's identity. The restaurant struggled during World War II because rationing constrained access to beef, but business improved after the war. The family eventually purchased the property that had initially been leased. Nellie Winstead and her husband, Gordon Montgomery, assumed control after Kathryn retired in 1952. They expanded the menu in 1957 by adding french fries and milkshakes. Kathryn died in 1967, and in 1969 the Montgomerys sold the business to Morris and Victor Lerner. The Lerners were associated with King Louie International and expanded Winstead's with restaurants in Kansas City North and Overland Park, Kansas. A former location in Lee's Summit later housed another restaurant, and a separate Independence location operated until its owner retired in 1952. King Louie International was sold to an investment group in 1982. The group considered closing or divesting the small restaurant chain, but local restaurateur Nabil Haddad became the figure responsible for preserving and operating Winstead's. The brand subsequently became part of Haddad Restaurant Group. It continued as a regional Kansas-Missouri chain rather than pursuing broad national expansion. The later history has included contraction of the store base. The Overland Park location on Metcalf Avenue closed in August 2015 when its lease expired, and the Lenexa restaurant closed on April 15, 2019. In 2020, Winstead's filed for Chapter 11 bankruptcy protection with more than $1.5 million in reported debt. The brand remains associated with Kansas City hamburgers, cheeseburgers, large shared beverages and its distinctive roadside architecture, although current operating details require verification.

• 2020

  Chapter 11 bankruptcy filing

  [1]Winstead'sen.wikipedia.org

  Winstead's sought Chapter 11 bankruptcy protection while owing more than $1.5 million, according to the cited reference.

• 2019

  Lenexa location closes

  [1]Winstead'sen.wikipedia.org

  The restaurant on West 95th Street in Lenexa closed on April 15.

• 2015

  Overland Park location closes

  [1]Winstead'sen.wikipedia.org

  The Metcalf Avenue restaurant in Overland Park closed when its lease expired.

• 1982

  Haddad assumes control

  [1]Winstead'sen.wikipedia.org

  After King Louie International was sold, Nabil Haddad became associated with operating and preserving the Winstead's chain.

• 1969

  Ownership passes to the Lerner brothers

  [1]Winstead'sen.wikipedia.org

  Morris and Victor Lerner acquired Winstead's from the Montgomerys and later expanded the chain.

• 1957

  Fries and milkshakes added

  [1]Winstead'sen.wikipedia.org

  The operators expanded the previously limited menu with french fries and milkshakes.

• 1952

  Kathryn Winstead retires

  [1]Winstead'sen.wikipedia.org

  Kathryn Winstead retired from restaurant operations and transferred control to Nellie Winstead and Gordon Montgomery.

• 1940

  Kansas City Winstead's opens

  [1]Winstead'sen.wikipedia.org

  The landmark restaurant near Kansas City's Country Club Plaza opened with indoor and outdoor service and a Streamline Moderne design.

• 1937

  Garst's Drive-In opens in Sedalia

  [1]Winstead'sen.wikipedia.org

  Winstead family members opened Garst's Drive-In in Sedalia, Missouri, as part of the family's move back toward its Missouri roots.

• 1936

  Kathryn Winstead establishes Winstead's Drive-In

  [1]Winstead'sen.wikipedia.org

  Kathryn Winstead founded the original Winstead's Drive-In in Springfield, Illinois, using an early carhop-service format.

A heritage Kansas City drive-in and hamburger brand combining classic American fast food with recognizable Streamline Moderne architecture and oversized shared drinks.

• Hamburgers · 1936

  Hamburgers and cheeseburgers

  Winstead's core offering is the classic griddled hamburger, particularly its cheeseburger. The burgers form the center of the brand's regional identity and have received favorable attention from food publications and critics.

• Side dishes · 1957

  French fries

  French fries were added to the historically limited menu in 1957 and became a standard accompaniment to the chain's burgers.

• Beverages · 1957

  Milkshakes

  Milkshakes were introduced in 1957 and remain part of the brand's traditional American drive-in menu. Winstead's is especially associated with oversized 'skyscraper' versions designed to serve several people.

• Beverages

  Skyscraper sodas

  The chain's unusually large sodas are known as skyscraper drinks. Their size and presentation are part of Winstead's distinctive legacy and help differentiate the brand from an ordinary hamburger counter.

• 2020

  Chapter 11 restructuringOther

  Background

  The regional chain faced reported debt exceeding $1.5 million amid a reduced restaurant footprint.

  Action taken

  Winstead's filed for protection under Chapter 11 of the U.S. Bankruptcy Code.

  Aftermath

  The filing placed the business in a court-supervised restructuring process. Detailed restructuring outcomes are not established in the supplied reference material.

  Reported debt. more than $1.5 million (2020 bankruptcy filing)

  Source

1. 1Winstead'sen.wikipedia.org