Six Legendary Cigars, 122 Years of Baseball, and the Private Miami Club Where the World Series Becomes a Ritual.
THE AIRWAYS CLUB | CORAL GABLES × COCONUT GROVE | OCTOBER 2026
On Friday, October 23, the 2026 World Series is scheduled to begin, bringing together the best of Major League Baseball for its 122nd championship series. The occasion is more than a sporting event. It is an American cultural institution built on strategy, tradition, rivalry, and the pursuit of excellence.
At The Airways Club, located at the crossroads of Coral Gables and Coconut Grove, we appreciate the connection between baseball's strategic patience and the deliberate craftsmanship of a premium cigar. Both have histories that transcend generations. Both reward knowledge, discipline, and an appreciation for detail.
And both have produced legends whose reputations outlived their greatest victories.
Six Cigars Worthy of the Fall Classic
Selecting a cigar for a World Series evening is not simply a question of strength or price. It is about character, construction, complexity, and the time one intends to spend enjoying it. A tightly contested pitching duel demands a different atmosphere from a decisive ninth-inning rally.
The following six selections offer distinct experiences for adult cigar aficionados who appreciate the traditions of both baseball and fine tobacco.
1. Montecristo Crafted by AJ Fernandez — The Franchise Player
The Montecristo Crafted by AJ Fernandez combines the heritage of a historic cigar name with the contemporary blending expertise of AJ Fernandez, one of Nicaragua's prominent tobacco producers.
Its Ecuadorian Sumatra Oscuro wrapper and blend of Nicaraguan and Honduran tobaccos create an assertive profile with notes commonly described as cedar, mocha, spice, and pepper. Like a franchise player who can influence an entire series, this cigar has sufficient complexity to hold an experienced aficionado's attention.
The history of Montecristo reflects the international development of premium cigar culture, while Nicaragua's Estelí tobacco-growing region illustrates how geography, soil, and cultivation shape the finished product.
For the World Series, it is a compelling choice for those who appreciate complexity without sacrificing balance.
2. Montecristo 1935 Anniversary Nicaragua — The Cleanup Hitter
Some cigars are designed to be approachable. Others make a more emphatic statement.
The Montecristo 1935 Anniversary Nicaragua belongs to the latter category. Produced as a tribute to Montecristo's founding year, this Nicaraguan puro is recognized for its substantial body, concentrated flavors, and sophisticated construction.
The blend's reputation has been reinforced by premium cigar critics, including publications such as Cigar Aficionado and Halfwheel, which regularly examine the craftsmanship and performance of contemporary cigars.
Its rich tobacco character and layered finish make it a natural conversation piece for enthusiasts familiar with Nicaragua's premium cigar industry.
In baseball terms, this is the cleanup hitter: confident, powerful, and expected to deliver when the stakes rise.
3. Oliva Serie O — The Reliable Veteran
Championship teams rarely depend exclusively on spectacular talent. They also need experienced performers who deliver consistent results under pressure.
The Oliva Serie O represents that principle exceptionally well.
Produced from Habano-seed tobacco cultivated in Nicaragua, including the celebrated regions of Estelí, Condega, and Jalapa, Serie O offers a medium-to-full-bodied profile with earthy tobacco, cedar, and spice.
Its Churchill vitola earned recognition in Cigar Aficionado's 2013 Top 25, reinforcing the line's established reputation.
The broader story of Oliva Cigar Co. is also a reminder that family expertise, agricultural knowledge, and manufacturing discipline remain central to premium cigar production.
Like a veteran starting pitcher, the Serie O does not require theatrical introductions. Its performance speaks for itself.
4. Boneshaker Mace — The Power Pitcher
Every World Series has moments when subtlety gives way to intensity: a bases-loaded confrontation, an unexpected home run, or a pitching change that transforms the game.
The Boneshaker Mace brings a similarly forceful personality to the humidor.
Built around a dark Connecticut Broadleaf wrapper, the blend is known for a full-bodied character featuring pepper, espresso, leather, and dark tobacco notes.
Connecticut Broadleaf occupies a distinctive place in American cigar agriculture, and its cultivation is part of the broader history documented by the Connecticut Agricultural Experiment Station.
The Boneshaker is not intended to be understated. It is an assertive selection for aficionados who appreciate intensity and strong flavor definition.
5. Gran Habano Connecticut #1 — The Leadoff Hitter
Not every great performance begins with a dramatic entrance. Sometimes the most effective opening is measured, elegant, and precise.
The Gran Habano Connecticut #1 embodies that philosophy.
Its Ecuadorian Connecticut wrapper contributes to a relatively gentle, creamy profile with toasted nuts, cedar, and subtle sweetness. Compared with the heavier selections in this lineup, it offers a more restrained introduction.
The Gran Habano brand represents a tradition of tobacco blending that combines Central American agricultural experience with modern production.
For aficionados who prefer a milder cigar during pregame conversation, the Connecticut #1 provides a fitting opening act.
6. Nub Connecticut — The Relief Specialist
Baseball managers understand that timing is everything. Not every pitcher is expected to work nine innings, and not every cigar experience requires an extended format.
The Nub Connecticut offers a distinctive short, thick format designed to deliver an established flavor profile relatively early in the smoking experience.
Its Ecuadorian Connecticut wrapper contributes to a creamy, mellow-to-medium-bodied character.
The Nub brand became known for challenging conventional expectations about cigar proportions, demonstrating that shorter formats can still offer substantial tobacco character.
It is an interesting example of how cigar makers continually experiment with format, combustion, and blend composition.
Baseball's Great Cigar Personalities: From Babe Ruth to Big Papi
The relationship between baseball and cigars is more than a marketing invention. It is woven into the sport's cultural history, particularly during an era when tobacco advertising, celebrity endorsements, and public smoking occupied a much larger place in American society.
That history deserves to be understood in its original context rather than romanticized without qualification.
Babe Ruth: The Sultan of Swat and the Cigar
Few athletes have influenced American popular culture as profoundly as Babe Ruth.
The New York Yankees legend became an international celebrity through his extraordinary home-run production, larger-than-life personality, and enormous commercial appeal.
Historical photographs frequently show Ruth with cigars, while tobacco endorsements became part of his public image. The National Baseball Hall of Fame preserves the broader story of how Ruth helped transform professional baseball into a national entertainment industry.
His celebrity also emerged during the golden age of American advertising, when athletes increasingly served as commercial spokesmen. The Smithsonian Institution documents the cultural and commercial history of American consumer products, including tobacco-related artifacts.
Ruth's cigar imagery belongs to that larger historical period, one in which athletic fame, business, and personal branding became increasingly intertwined.
Luis Tiant: The Cuban Connection
The late Luis Tiant, celebrated for his distinctive pitching delivery and memorable career with the Boston Red Sox, embodied the close cultural relationship between Cuba and American baseball.
His career also reflected the extraordinary influence of Cuban athletes on Major League Baseball, a history explored by the Society for American Baseball Research and the National Baseball Hall of Fame.
Tiant later lent his identity to the El Tiante cigar brand, connecting his baseball legacy to another deeply rooted Cuban tradition.
For Miami, a city shaped by Cuban immigration, entrepreneurship, and baseball enthusiasm, Tiant's story carries particular cultural significance.
The relationship between Cuban tobacco and international cigar culture is also documented through organizations such as Habanos S.A., whose brands remain central to discussions of Cuban cigar heritage.
David Ortiz: From Championship Hero to Cigar Entrepreneur
Few modern baseball personalities have connected championship success and cigar culture as visibly as David Ortiz.
The former Boston Red Sox designated hitter, affectionately known as Big Papi, helped redefine the franchise's modern history through his postseason performances and three World Series championships.
Beyond baseball, Ortiz developed commercial relationships within the cigar industry, including a signature collaboration with El Artista Cigars.
His transition from professional athlete to entrepreneur illustrates a broader phenomenon: prominent athletes building businesses around their personal interests and reputations.
The business of athlete endorsements and licensing has become a significant part of professional sports, with organizations such as MLB Players, Inc. playing an important role in commercial partnerships.
For Ortiz, cigars became another expression of an identity already associated with confidence, celebration, and Dominican heritage.
Jack McKeon: The Manager Who Followed His Own Rules
Miami baseball has its own cigar legend.
When Jack McKeon managed the Florida Marlins to the 2003 World Series championship, his distinctive personality and well-known affection for cigars became part of the team's national story.
McKeon was an old-school baseball figure: direct, experienced, strategically independent, and largely indifferent to fashionable management theories.
The Marlins' championship victory over the Yankees remains one of the defining achievements in South Florida sports history, recorded in MLB's World Series archives.
His managerial philosophy also offers an enduring business lesson: leadership is not always about being the loudest or most modern person in the room. Sometimes it is about making the correct decision when everyone else is watching.
The 2026 World Series: Two Teams, One Historic First
This year's championship offers an especially compelling narrative. The Milwaukee Brewers will face the Tampa Bay Rays, beginning October 23 at 8 p.m. Eastern.
Neither franchise has ever won a World Series. One will finally claim its first championship.
The matchup is particularly intriguing because both organizations have demonstrated that financial resources alone do not guarantee success. In a league where payroll disparities frequently dominate discussion, Milwaukee and Tampa Bay have reached baseball's biggest stage through roster development, strategic management, and organizational execution.
According to Associated Press reporting, the two franchises are among MLB's comparatively lower-payroll teams, offering a striking contrast to the sport's traditional financial powerhouses.
For Miami's entrepreneurs and executives, the parallel is unmistakable. The biggest budget does not always win. The smartest allocation of capital, the strongest leadership, and the ability to execute under pressure can prove more decisive.
Those interested in the economics of baseball can explore research from Forbes, the statistical analysis of FanGraphs, and historical performance data maintained by Baseball Reference.
This World Series is not merely a contest between two baseball teams. It is a case study in competing successfully against organizations with greater financial resources.
Why Baseball and Private Clubs Share a Common Culture
A baseball game can turn on a single decision made after hours of preparation. Business negotiations operate under a similar principle.
The best executives understand that effective decision-making requires patience, observation, timing, and the willingness to act decisively when an opportunity presents itself.
That is one reason private clubs have historically played a meaningful role in professional relationships.
Institutions such as The Players in New York and the Union League of Philadelphia reflect the longstanding American tradition of membership communities organized around conversation, culture, and professional association.
In Miami, the demand for private environments exists alongside a dynamic economy shaped by international investment, finance, real estate, and entrepreneurship.
Organizations such as the Greater Miami Chamber of Commerce and the Miami-Dade Beacon Council illustrate the scale and diversity of the region's business community.
At The Airways Club, we see privacy not as an incidental amenity, but as a defining part of the membership experience.
A private conversation can be more valuable than a crowded networking event. An uninterrupted discussion can reveal more than a dozen hurried introductions. And an environment designed for discretion allows members to engage with one another without the distractions of conventional public venues.
Our philosophy is straightforward: cigars, conversation, and confidentiality.
The Airways Club: Where the World Series Meets Miami's Private Business Culture
Located at the crossroads of Coral Gables and Coconut Grove, The Airways Club brings together the traditions of a private cigar lounge and the practical value of a professional meeting environment.
Our approach differs from that of a conventional sports bar. We believe a significant sporting event can be appreciated without sacrificing discretion, atmosphere, or meaningful conversation.
For members, the appeal extends well beyond baseball. The club is designed around the idea that professional relationships often develop outside formal conference rooms, through shared interests and conversations that cannot be scheduled into a fifteen-minute appointment.
That philosophy has deep roots in the history of private social institutions. The Club Managers Association of America represents professionals responsible for operating private clubs, while Club + Resort Business covers the evolving expectations of private-club members.
The modern private club must offer more than exclusivity. It must provide a meaningful reason to belong.
For The Airways Club, that reason begins with privacy and extends into the relationships, professional environment, and traditions of cigar appreciation that define our membership concept.
December Membership Applications: A Private Invitation
As the 2026 World Series approaches, The Airways Club is also preparing for its next membership chapter.
Applications for December membership are now being accepted.
Our private men's club is intended for individuals who appreciate the craftsmanship of premium cigars, the importance of confidentiality, and the value of spending time among accomplished professionals.
The club's location between two of Miami's established business communities creates an appealing setting for members whose professional lives connect Coral Gables, Coconut Grove, Brickell, and the broader South Florida market.
We invite prospective members to learn more about our philosophy and membership opportunities through our official website.
Because the most important moments are not always the ones witnessed by a stadium full of people. Sometimes they happen in a private room, among individuals who understand the value of discretion.
THE WORLD SERIES ENDS. THE CONVERSATION CONTINUES.
Cigars. Conversation. Confidentiality.
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