This profile is in active compilation — some details are awaiting a cited source.

Winstead’s Steakburgers is Kansas City’s Streamline Moderne steakburger diner. Kathryn Winstead’s family opened the Plaza room in 1940 (the fifth Winstead’s, after Springfield, Illinois, 1936). Two rooms remain: the Plaza flagship at 101 Emanuel Cleaver II Blvd and Winstead’s Row at 10711 Roe Ave, Overland Park. Known for steakburgers, a 50/50 onion-ring-and-fries side, Skyscraper shakes, and a Plaza drive-thru that still runs around the clock. Tier 1 — KC-operated heritage brand under the Haddad family since 1988 (contracted from a regional chain to these two rooms after a 2020 bankruptcy).123

Description

The Plaza Winstead’s is the Streamline Moderne building just east of the Country Club Plaza — originally a drive-in and sit-down room, the first of the chain built that way. Carhops once took headlight signals in the lot; the interior still reads 1950s diner (mint booths, neon, a jukebox), even as the physical room has worn. Kansas City Magazine’s February 2026 visit found the Plaza packed on a Friday night, with general manager Sarah Hibbert crediting location, price, field trips, lunch professionals, and late wedding catering.2

The signature is the steakburger — thin, beefy, “with the works” (ketchup, mustard, pickles, a whole onion slice). Sides include the house 50/50 (onion rings and fries). Shakes and the Skyscraper remain the dessert identity; a cherry limeade with green sherbet is still on the Plaza floor. Calvin Trillin, in the 1970s, called the steakburger an exercise in “monumental purity.”2

Ownership and history

Kathryn Winstead opened the first drive-in in Springfield, Illinois, in 1936. Sisters expanded to Jacksonville, Fort Wayne, and Sedalia before the 1940 Plaza room — the first designed as Streamline Moderne sit-down plus carhop. The family later bought the Plaza parcel from J.C. Nichols. Fries and frosty malts were added in 1957. Mid-century growth put rooms in Independence, Lee’s Summit, North Kansas City, Lenexa, Overland Park, and Olathe; nine metro locations still existed about a decade before 2026.2

Nabil Haddad (Baghdad-born, longtime KC McDonald’s franchisee) bought the brand in 1988 when it still had about a dozen rooms in the metro plus Illinois and Indiana. The Haddad Restaurant Group later also ran Plaza III and Fred P. Ott’s. Over-expansion reversed: rooms closed through the 2010s; the Leawood Winstead’s closed in 2020. Haddad Restaurant Group and The Winstead’s Company filed Chapter 11 that year. A confirmed subchapter V plan for Winstead’s was reported to run through March 2028; a 2022 Kansas bankruptcy opinion still listed the Haddads owning 93.45% of The Winstead’s Company (personal stock plus revocable trust; children holding the rest), with David Haddad as president drawing a salary under the plan. The first-party site still lists a Haddad contact email. Two rooms remain: Plaza and Roe / “Winstead’s Row.”3421

Last verified: 2026-08-12 · Source: official site (item photos / section cues) + KC Mag floor visit · menu_status: partial (first-party menu page exists; prices not transcribed this pass)

  • Steakburger — thin steakburger; “the works” = ketchup, mustard, pickles, whole onion slice; bacon available2
  • 50/50 — onion rings and fries (the house split side)2
  • Skyscraper shake — the brand’s oversized shake2
  • Cherry limeade — fresh lime, scoop of green sherbet (Plaza visit)2
  • Also on the official photo menu: bacon cheeseburger, chili cheese dog, BLT, crispy chicken salad, banana split, cheesecake1

Sources

Footnotes

  1. Winstead’s Steakburgers first-party site (accessed 2026-08-12). Asserts: Plaza 101 Emanuel Cleaver II Blvd, Kansas City, MO 64112; Winstead’s Row 10711 Roe Ave, Overland Park, KS 66211 (homepage also prints 66207 — ZIP conflict flagged, 66211 used as the Roe/Leawood-corridor listing on the same page’s Row block); contact david.haddad62@gmail.com; photo menu of burgers, rings, shakes, desserts. ↩ ↩2 ↩3

  2. Tyler Shane, “Let’s Talk About Winstead’s: The beloved institution where nostalgia reigns supreme,” Kansas City Magazine, Feb 21, 2026 — asserts: 1936 Springfield founding; 1940 Plaza Streamline Moderne (fifth location); fries/malts 1957; Trillin “monumental purity”; Haddad buy 1988; 2020 bankruptcy and Leawood close; two rooms left (Plaza + I-435/Roe); Plaza 24/7, drive-thru, cheap menu; GM Sarah Hibbert (~four years); steakburger-with-works, 50/50, cherry limeade with green sherbet; Skyscraper shakes. ↩ ↩2 ↩3 ↩4 ↩5 ↩6 ↩7 ↩8 ↩9

  3. Laura Spencer, “Kansas City’s Iconic Winstead’s Steakburgers Files For Chapter 11 Bankruptcy,” KCUR, Mar 10, 2020 — asserts: 2020 filing; Haddad Restaurant Group also filed Feb 2020; Nabil Haddad purchased 1988 (~dozen metro + IL/IN); three rooms at filing (Leawood 4971 W 135th, OP 10711 Roe, Plaza 101 Emanuel Cleaver II Blvd); Fred P. Ott’s already closed. ↩ ↩2

  4. Fox4 KC, “Winstead’s files plan to pay off debt, continue operating after bankruptcy,” Nov 25, 2020 — asserts: Nabil and Peggy Haddad majority 96%, David Haddad 3%, Samia Haddad 1% at plan time. Ownership later restated in In re Haddad, Bankr. D. Kan. No. 21-20961 (Sept 13, 2022 opinion) as Haddads 93.45% of The Winstead’s Company (29.5% personal + 63.95% revocable trust; children the rest); David president; Winstead’s own 2020 Ch. 11 plan through March 2028; two restaurants Plaza + Overland Park. PDF: ksb.uscourts.gov ↩

See also

Categories

On the record — ks.city/registry/winsteads-steakburgers · record updated 2026-08-12