Winton Smith

“Father of the Tennessee Squire Association”

In the early 1950s, the Jack Daniel Distillery was still a relatively small but growing operation that had not yet been purchased by Brown-Forman. At that time, it was still getting back on its unsteady feet after the “double-whammy” of Prohibition, which had lasted 13 years longer in Tennessee than any other state, followed by World War II, when all alcohol production had been diverted to making ethanol for the war effort.

The mellow Tennessee Whiskey had already acquired a glowing reputation among whiskey lovers, but at that time, it was far from being a household name. The four Motlow Brothers: Conner, Hap, Reagor, and Robert,  had recently inherited the distillery from their late father Lem, and the boys were working hard to spread the name and reputation of their locally beloved, but not yet nationally recognized product.

The distillery had also recently hired brilliant marketing whiz Art Hancock, and Hancock had interestingly begun advertising aggressively at a time when demand already exceeded supply. So, from the mid-1950s to the 1970s, the company sold its product solely on allocation. The sales representatives would literally go into an establishment and let them know how many cases, or even single bottles, they could have.

Hancock’s ads, conceived and fed to national magazines, were simply, ‘We’d rather ask for your patience than your forgiveness.’ The company was spending big money on ads telling people they couldn’t get any product! What the ads related was, essentially, ‘We’re not going to compromise the quality of the product. You might have to wait a while, but you’ll always get the original Jack Daniel’s, not some cheaper, lower-quality substitute.’ The ads were a tremendous success, and sales in Lynchburg began to explode. It seemed that people wanted even more of something if they realized they couldn’t have it.

Since it took a few years for Jack Daniel’s to mature, the distillery found its supplies running dangerously low. There were just more orders than there was whiskey to supply them. People who loved the taste of Jack Daniel’s began writing to the Distillery, and folks at the Distillery actually started writing back to customers, keeping in touch until production could meet demand. It was soon decided that something special ought to be done for the unfulfilled but faithful fans of Lynchburg’s favorite commodity.

With this in the mind of everyone at Jack Daniels, in 1956, Winton Smith, Jack Daniel’s then-President, who had been the company’s first National Sales Director, was on a business trip to Texas, and he saw a sign at an airport cigar stand, “Buy a Square Inch of Texas for One Dollar.” The ad sparked an idea in Smith, and he couldn’t wait to take the idea back to ad man Hancock. The two of them knew right away that they were on to something.

So Winton decided that loyal fans who had written the distillery saying they could not get any Jack Daniel’s whiskey would instead receive a “plot” of land, a single square inch of unrecorded property on the distillery’s grounds. This would make them part owners, or Squires, and these would be the first members inducted into the Tennessee Squire Association.

Some Squires have wondered if Lem Motlow or even Mr. Jack was the first member. But, actually, the Squire Association will be celebrating its 70th birthday in February of 2026. Ownership of a square inch of the Distillery land is generally unproblematic. From time to time, however, Squires request to graze their cattle on it, and occasionally, people call to report trouble with coyotes, skunks, or possums on their “land”. By and large, however, peace reigns.

Despite the lighthearted nature of its members, the Tennessee Squire Association is an exclusive club, with many prominent members from government, business, and entertainment, the most famous of whom is arguably Frank Sinatra. To become a Squire, one may only be nominated by an existing Squire, and by tradition, each Squire can then only nominate one member in his or her lifetime. There is also a secret room reserved for Squires at Lynchburg, and not even the tour guides are allowed to mention it.

The thing that ties all Squires together is their love for Jack Daniel’s Tennessee Whiskey and an appreciation for friendship. As Winton Smith originally wrote in the very first letter to Squires, “It is just our feeling that too little time is spent in this day and age enjoying the friendship of others. This is our attempt to help people change that.”

As for Winton Edward Smith, not much is known about his life pre-Jack Daniels. He rose from JD’s Sales Director to the position of President in 1953, at the age of 41. Winton married Irene B. Smith in the 1940s, and that marriage lasted until 1986. It was also in 1986 that Smith granted an ultra-rare, exclusive interview with the University of Louisville, discussing bourbon and Tennessee whiskey and specifically Brown-Forman’s takeover of Jack Daniels, production, competition, and the management of a distillery.

One of the most famous stories involving Winton Smith occurred in 1967, when Frank Sinatra, who, famously, had a near-infatuation with Jack Daniels (and was ultimately buried with a bottle of it), couldn’t find any of his beloved whiskey anywhere in Las Vegas. Sinatra reportedly called his longtime friend and then-President of Sales for Jack Daniel’s, Angelo Lucchesi, and said, “Angie, help me out here, one Italian to another!” So Luccesi called Hap Motlow, whom he told, ‘Get hold of Winton Smith.’ Smith told Motlow simply, “Hang on,” then, after a short pause, “It’s done,” then Smith simply hung up. Winton was later quoted as confiding to some of his friends that it was “No easy task” keeping Ol’ Blue Eyes awash in Jack Daniel’s.

Winton Smith retired from Jack Daniels in the early 1980s. Later, he married Mary Alice Kent Simpkins when he was 73 and she was 68. Winton enjoyed sharing her three children and his extended step-family up until he died in 2000 at the age of 88 in Nashville, where he was also buried.

Contributed by Tracy McLemore, Fairview, Tennessee