Inside Chicago’s historic Board of Trade building, a century-old tobacconist preserves a remarkable history of financial traders, famous customers, and the man who started it all in 1921.
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In the 1990s, a Chicago trader walked into Jack Schwartz Importer after losing $800,000 in the financial markets.
He settled into the back office, lit a cigar, and checked on his trades. Within five minutes, his losses had narrowed to $200,000.
The remarkable encounter was recalled by then-owner Joe Howe in a November/December 1997 Cigar Aficionado feature titled Hedging Stress.
It was an extraordinary afternoon, but not an entirely unusual setting.
Just across the street from the Chicago Board of Trade, Jack Schwartz Importer had become a familiar gathering place for some of the city’s most successful financial traders. Fortunes could be won or lost in minutes on the exchange floor, and the little tobacco shop offered a place to escape the intensity of the markets.
Yet the story of Jack Schwartz Importer extends far beyond Chicago’s financial district.
Believed to be the youngest known photograph of Jack Schwartz inside his Chicago cigar shop. According to current owner Billy O’Hara, the exact year remains unknown, making this a rare glimpse into the early life of the man who founded Jack Schwartz Importer in 1921.
Founded in 1921, the business has survived more than a century of changing ownership, locations, and smoking culture. Its history includes an encounter with Winston Churchill, generations of Chicago businessmen, and a particularly interesting connection to the famous building it now occupies.
During my recent travels through Chicago, I had the opportunity to visit Jack Schwartz Importer myself, explore its historic interior, and learn more about the people and stories behind this remarkable establishment.
Founded in 1921: The Beginning of Jack Schwartz Importer
Jack Schwartz opened his tobacco business in Chicago in 1921, beginning what would become one of the city’s longest-running tobacconist traditions.
At the time, Chicago was already a major center of American commerce. Banks, trading houses, and commercial institutions dominated the downtown financial district, while traditional tobacco shops remained a familiar part of urban life.
These establishments were more than places to purchase tobacco. A neighborhood tobacconist could also serve as a social destination, where customers developed relationships with shopkeepers, exchanged news, and returned regularly to discuss business and everyday life.
Jack Schwartz built his business within this culture.
Although relatively little detailed biographical information about Schwartz’s earliest years has been preserved in widely available sources, the company he established in 1921 continued to grow into a recognized name among Chicago cigar enthusiasts.
One particularly fascinating aspect of the shop’s history is that it actually predates the building in which it currently operates.
The present Chicago Board of Trade Building, designed by the architectural firm Holabird & Root, officially opened in June 1930—nine years after Schwartz founded his business.
The famous 45-story Art Deco skyscraper stands at the southern end of LaSalle Street, crowned by a towering aluminum statue of Ceres, the Roman goddess of agriculture.
Today, Jack Schwartz Importer occupies a space within this architectural landmark. However, the business did not relocate into the building until 2000.
For much of its earlier history, the shop operated elsewhere in Chicago’s financial district, including a location directly across the street from the Board of Trade.
That proximity would become one of the defining characteristics of the business.
A Sanctuary for Chicago’s Financial Traders
By the 1990s, Jack Schwartz Importer had developed an extraordinary relationship with Chicago’s trading community.
The Chicago Board of Trade and neighboring financial exchanges were home to a famously intense world of open-outcry trading, where traders in colorful jackets shouted orders, signaled transactions by hand, and made enormous financial decisions in seconds.
Within this environment, a nearby cigar shop could provide a welcome change of pace.
In 1997, journalist Alejandro Benes documented this relationship in Cigar Aficionado, describing the remarkable personalities who frequented Jack Schwartz Importer.
Among them was Tom Baldwin, one of the most prominent traders in Chicago’s Treasury-bond market.
Baldwin was known for handling enormous positions and experiencing financial swings that most people could scarcely imagine.
It was Baldwin whom Joe Howe recalled arriving at the shop after suffering the $800,000 trading loss described earlier.
Other notable Chicago traders also maintained connections to the establishment. The shop offered an atmosphere where customers could talk about markets, exchange stories, and spend time among people who understood the extraordinary pressures of their profession.
The 1997 feature also documented a Jack Schwartz Cigar Club, with Chicago Board of Trade broker Paul R. T. Johnson Jr. serving as its vice president.
This relationship was an important part of the shop’s identity long before it occupied its present location.
The connection between cigars and Chicago’s trading floors was not simply a coincidence of geography. It grew from the people who worked in the district, their shared experiences, and the familiarity they developed with the establishment over many years.
For some customers, Jack Schwartz was a regular stop between trades. For others, it was a place to celebrate a successful day or recover from a particularly difficult one.
The shop had become part of the social history of Chicago’s financial community.
Winston Churchill and Jack Schwartz: A Remarkable Encounter
An original photograph of Winston Churchill examining cigars, with the Montecristo brand name clearly visible on the box in the foreground. Interestingly, the branding was later removed from subsequent versions of this historic image, making this an especially fascinating piece of cigar history.
Among the most fascinating stories associated with Jack Schwartz Importer is the founder’s connection to British Prime Minister Winston Churchill.
Churchill remains one of history’s most recognizable cigar smokers. His public image became so closely associated with cigars that photographs of him holding or smoking one are among the most enduring images of the twentieth century.
According to Jack Schwartz Importer’s published company history, Schwartz met Churchill during the 1940s.
During my visit, current owner Billy O’Hara shared an additional detail with me: Jack Schwartz personally sold Winston Churchill a cigar when the two men met.
It’s a remarkable piece of the establishment’s history, particularly considering Churchill’s reputation as one of the world’s most famous cigar enthusiasts.
The story also provides an interesting glimpse into the clientele that a respected tobacconist could encounter during the mid-twentieth century.
While the exact circumstances of their meeting remain less thoroughly documented than other chapters of the business’s history, the encounter continues to be remembered as part of the Jack Schwartz story.
Inside the shop today, historic photographs help preserve these connections to the past, including images of the founder and earlier chapters of the business.
Seeing these photographs in person was one of the particularly interesting parts of my visit.
Billy O’Hara: From Chicago’s Trading Floors to a Historic Tobacconist
The story of Jack Schwartz Importer took another important turn in the late 1990s.
Billy O’Hara, who had spent much of his professional life in Chicago’s financial markets, became the owner of Jack Schwartz Importer in 1998.
His connection to the establishment had begun several years earlier.
According to the 1997 Cigar Aficionado article, O’Hara had previously spent approximately seventeen years trading at the Chicago Board Options Exchange before joining the shop as its manager.
His background made him particularly familiar with the clientele and culture that surrounded the business.
Unlike an owner arriving from an unrelated industry, Billy already understood the financial community that had helped make Jack Schwartz an institution.
In 2000, he oversaw a significant new chapter in the shop’s history when the business relocated into the Chicago Board of Trade Building at 141 West Jackson Boulevard.
For a tobacconist that had spent years serving Chicago’s financial traders from across the street, moving into one of the city’s most recognizable financial landmarks was a fitting development.
The relocation also placed the historic business within one of Chicago’s finest examples of Art Deco architecture.
More than two decades later, Billy continues to carry forward the business founded by Jack Schwartz.
The shop remains associated with traditional cigars and tobacconist culture while maintaining a substantial modern inventory.
Its longevity is particularly impressive considering how dramatically American tobacco retailing has changed since the business first opened.
Inside Jack Schwartz Importer Today
Stepping inside Jack Schwartz Importer, I was immediately drawn to its warm wooden interior, glass cigar displays, and intimate seating areas. Historical photographs line the walls, including portraits of Jack Schwartz himself and images of the shop’s earlier location, offering a fascinating glimpse into its past.
One of the highlights of my visit was opening a fresh box of Westminster cigars, Jack Schwartz’s longstanding house brand. I documented the process, from carefully cutting the seal to sliding open the box and revealing the cigars inside. It was particularly interesting to experience a cigar line that remains part of the establishment’s legacy more than a century after its founding.
Between the original photographs, traditional furnishings, and Westminster cigars still produced today, Jack Schwartz Importer offers something increasingly uncommon: a historic tobacconist where the past isn’t simply remembered, but remains part of the experience.
Preserving More Than a Century of Chicago Cigar History
Chicago has changed tremendously since Jack Schwartz opened his tobacco shop in 1921. Financial markets have evolved, historic businesses have disappeared, and traditional tobacconists have become increasingly uncommon. Yet through more than a century of change, Jack Schwartz Importer has endured.
Its longevity is remarkable, but what makes the establishment especially interesting is the history it has accumulated along the way. From its connections to Chicago’s financial community to the personalities who passed through its doors, the shop has become part of the city’s cultural heritage.
Visiting Jack Schwartz Importer reminded me how much history can exist inside a place that thousands of people might walk past without a second thought. These establishments preserve more than merchandise; they carry the stories, relationships, and traditions of generations past.
More than a hundred years after its founding, Jack Schwartz Importer remains a living piece of Chicago history, fittingly housed within one of the city’s most iconic buildings.
Jack Schwartz Importer is located inside the Chicago Board of Trade Building at 141 West Jackson Boulevard, Chicago, Illinois. Learn more about the establishment at JackSchwartz.com.
Historical research draws upon the shop’s official history, Alejandro Benes’s 1997 Cigar Aficionado feature Hedging Stress, and architectural histories of the Chicago Board of Trade. The account of Winston Churchill’s cigar purchase was shared directly with the author by owner Billy O’Hara.
Visit Jack Schwartz Importer
Founded in 1921, Jack Schwartz Importer continues to welcome visitors inside the historic Chicago Board of Trade Building in downtown Chicago’s Financial District.
Address: 141 W. Jackson Boulevard, Lobby 103, Chicago, IL 60604
Phone: (312) 782-7898
Email: [email protected]
Official Website: www.jackschwartz.com
Instagram: @jackschwartzcigars
Typical Store Hours: Monday–Friday, 9:00 AM–5:00 PM. Closed weekends. Contact the shop to confirm hours before visiting.
The entrance to the historic tobacconist inside the Chicago Board of Trade Building at 141 West Jackson Boulevard. More than a century after its founding in 1921, Jack Schwartz Importer continues to preserve a remarkable piece of Chicago’s cigar history.
This article is part of History of Smoke’s ongoing documentation of historic tobacconists, smoking establishments, and the people preserving their history.