Big Deal Speakeasy Casino, founded by entrepreneur Wendy Rubin, is New York City’s only 1920s-themed speakeasy casino and licensed dealer academy, offering hands-on gaming instruction by day and glamorous private casino events by night. With vintage design, craft cocktails, and professional dealers, the venue delivers a uniquely immersive experience for corporate groups, private parties, and anyone seeking unforgettable entertainment.
Tucked away behind a discreet entryway in Manhattan, the Big Deal Speakeasy Casino offers something you won’t find anywhere else in New York: a 1920s-themed speakeasy casino that also doubles as a licensed dealer academy by day. Founded by serial entrepreneur Wendy Rubin, the venue bridges two worlds—education and entertainment—while delivering an unforgettable experience that feels equal parts glamorous, interactive, and delightfully unexpected.
The Big Deal Casino Academy is New York’s only licensed casino school, offering immersive lessons in poker, blackjack, craps, and roulette. The atmosphere is supposedly a more lively workshop than a traditional class during the day, as students wouldn’t be just listening to instructions; they’d be rolling dice, stacking chips, and learning strategy hands-on at professional-grade tables. Specialized courses like Beginning Texas Hold’em for Women and Intermediate Poker for Women especially stand out to me for encouraging confidence and skill in a traditionally male-dominated space. Private coaching is also available, ensuring that players at any level can sharpen their game while keeping the mood light and fun.
The dealers were excellent at their craft
—courtesy of Big Deal
When the lights dim, however, the academy transforms. By night, the space becomes the Big Deal Speakeasy Casino—an invitation-only lounge where private groups enter with a whimsical password and are greeted by professional dealers at vintage casino tables. This is when I was able to experience the casino, and I can say that from top to bottom, the attention to detail in creating a Prohibition-era experience is unmatched, complete with jazz tones, art-deco details, and costumes for all employees that stick to the glamor and style of the 1920s. When I walked up to where the entrance supposedly resided, I was greeted by a man dressed in an old-fashioned 3-piece suit, sticking out like a sore thumb in Manhattan’s busy streets. I immediately knew this was the right place, and with a smile, he escorted me up a clanging old elevator.
Reaching the top, I was greeted by more individuals wearing flapper-esque dresses, and I marveled at the venue as they showed me around. A hidden entryway opened into a richly decorated 2,000-square-foot room that felt plucked from the Jazz Age. Plush velvet seating, dramatic lighting, and vintage casino tables transported me to another era, while Art Deco accents completed the sense of time travel. The flexible floor plan clearly made it equally suited to intimate gatherings of twenty or corporate buyouts of more than 100, with room for both cocktail mingling and full-on gaming excitement. I had no problem believing how much the venue had risen in popularity, becoming a favorite for companies and groups looking for something different: in a city where corporate events are typically boring bar nights, something like this is much more memorable. Groups clearly flock here not just for the games, but for the high-energy team-building and entertainment that turns an evening into an unforgettable event.
The 1920’s 1920s-inspired costumes were given maximum attention
—courtesy of Big Deal
The real fun started once I actually began playing the games. I am by no means a hardened casino-goer; if anything, the only game I was familiar with was poker (which I am terrible at and still needed the hand cheat-sheet). The casino started me out with two chips worth $2,000, and I was anxious as I sat down at a table. However, the dealers really did take their job as teachers first seriously, as they not only encouraged players and kept the energy and intensity up, but they also removed the intimidation factor by lightheartedly giving suggestions, explaining rules, and tossing free chips to players to keep the motivation going. While I cannot say that every chip I had at the end of the night was rightfully earned, I did learn a lot and had an amazing time. Especially games like Craps, which have a multitude of rules, can get confusing and stressful, but here they were elucidated and made much more enjoyable by the dealers. This was only helped by the amazing drink selection. The list leaned into craft cocktails, premium wines, and champagne service, often with theatrical presentations by the bartenders that I loved. The result was a customizable drinking experience that enhanced the casino’s buzzing atmosphere without ever overshadowing it, and I knew it would be perfect for any corporate event.
I loved the cocktail offering of the moody bar setup
—courtesy of Big Deal
The Visionary Behind the Venue
At the helm of this intriguing experience is Wendy Rubin, a creative force whose career defies easy categorization. Rubin founded the Big Deal Casino Academy in 2014 and launched the speakeasy casino the following year, creating the city’s only venue of its kind. Her track record spans far beyond casinos and hospitality: she has also produced award-winning films and commercials, pioneered the first online independent CD store, and developed one of the most syndicated college radio shows of its era. In less than a decade, Big Deal has hosted more than 500 corporate and private events for clients ranging from American Express and my own company, Barclays, to Getty Images and TD Bank. Rubin’s ventures thrive on boldness and originality, and this one is no exception. I know that in a city like NYC, it is getting harder and harder to be innovative and provide novelty, but Big Deal has carved out a space that feels genuinely rare.
After learning about both sides of Big Deal—the educational atmosphere of the academy, and then experiencing the glamorous buzz of the speakeasy in person—it’s clear why the venue has earned its reputation. It’s not just a casino, and not just an event space. It’s a carefully designed escape that combines play, learning, and performance in one immersive package. Competition for attention is fierce in NYC, but Big Deal Speakeasy Casino stands out as an experience that’s at once polished, playful, and unlike anything else to offer in this city. I myself have already looked into how I can book this venue for a birthday or corporate event, and I suggest you do the same, as dates are flying fast and this venue is clearly a Big Deal.
