The 1950’s Windsor Castle (ultra rare Red & Natural) chess set by “Leo Gladstone?”.

What they did…

The Windsor Castle chessmen in red and natural plastic are an exceptionally rare find. This set, housed in its original mahogany hinge-top box, features a double-sided, felted, and slotted interior, preserving its historical integrity. The King stands at 3.8 inches tall with a 1.6-inch diameter base, and each piece is heavily weighted with green felt base pads.

Crafted from a brittle plastic, most surviving examples exhibit severe chipping around their bases. However, this particular set is in near-perfect condition—an extraordinary rarity. Originally available in black or red and natural, these chessmen could be purchased in both weighted and unweighted versions, with the weighted ones typically showing more wear over time. A later production run in the late 1960s introduced a different plastic composition and pure white pieces, often packaged in faux alligator leatherette snap cases.

Throughout the 1950s and 1960s, Windsor Castle chess sets were a mainstay in American chess clubs and tournaments, prominently featured on Chess Review covers and in photographs. Despite their widespread presence, they mysteriously vanished, and today, even the Continental Chess Association, which once owned hundreds, is unable to locate a single example.

Now nearly extinct, these chessmen are highly prized by collectors, with even damaged sets commanding high auction prices. Red and natural sets, like the one featured here, are particularly scarce, with only a handful known to exist. This specific set, remarkably well-preserved, is believed to be one of few, of the finest example in existence.

The earliest recorded appearance of Windsor Castle chessmen dates back to December 1948 at the Manhattan Chess Club. During the New York International Tournament (December 23, 1948 – January 2, 1949), which was won by Reuben Fine, these sets were used in at least some of the matches. Photographs from the January 1949 issue of Chess Review show Fine using a Windsor Castle set against Al Horowitz and Arthur Bisguier playing with the set against Miguel Najdorf.

Additional images from the February 1949 issue further confirm their presence, with Miguel Najdorf and Max Euwe both using Windsor Castle pieces. The April 1949 cover of Chess Review features a portrait of Arthur Bisguier playing with this set, further solidifying its association with elite players of the era.

By June 1949, Windsor Castle chessmen were being advertised commercially in Chess Review by Leo Gladstone, with an initial price of $15.65. The ad emphasized their authentic Staunton design, regulation club size (4-inch King), and durable felted bottoms. This advertisement reappeared in October 1949 and again in October 1950, with a slight price increase to $16.65.

The sets first emerged in the New York chess scene, likely sourced or produced in the United States through Gladstone’s business. Despite their widespread use—evidenced by their presence in photos of notable players like Bobby Fischer and their prominence in events like the 1958 U.S. Chess Championship—the origin of these sets, and their disappearance remains one of chess collecting’s great unsolved mysteries.

My opinion of this design…

I value this set’s accessibility within the world of collectibles. While some vintage chess sets come with low price tags, the Windsor Castle set is generally more expensive, making it a desirable and hard to obtain option for both seasoned collectors and enthusiasts seeking a quality, playable vintage item. This combination of style, historical appeal, and extreme rarity makes the Windsor Castle Tournament Chess Set a prized item for serious players and vintage lovers alike.​ I am honored to own and play with this set!