It’s in the Cards: How to Plan the Perfect Poker Night

The perfect guys night: Playing poker in a grand room, cigar in hand, sipping a great whiskey, with good food at hand.

Highclere Castle Cigar CEO and co-founder Adam von Gootkin is the master of hosting poker nights like this and are very reminiscent of those that used to occur regularly at Highclere Castle, the regal home of TV drama series Downton Abbey, as well as in private clubs like the Hartford Club in Connecticut.

Von Gootkin sat down with The Manual to teach us how to host the perfect gentleman’s poker night, complete with real clay betting chips and red velvet smoking jacket.

“The goal is to host a poker night as fun as the game itself,” says von Gootkin. “A lot of guys treat poker night like football night, in a basement with beer and chips. While there’s nothing wrong with that, what’s fun is challenging yourself to step it up and put on an old-fashioned flavored poker night. That means better food, turn off the TV, quality cigars and great whiskey … your friends will thank you for it.”

Here are von Gootkin’s seven steps to win your poker night.

Step No. 1: Pick the Right Venue

In the past, the gentleman retired to, say, the castle library or smoking room for a cigar and card playing. If I’m hosting a poker night I’ll have it at a cigar lounge (check out these luxury clubs around the world) like Mickey Blakes in Milford, Connecticut, or at someone’s club since I’m seeking to craft a gentleman’s experience. There’s nothing wrong with hosting in your basement or man cave but if you’re able to play in a grand room, a historic house, with fireplaces, leather chairs, and high ceilings, play there.

Step No. 2: No Phones

You’re welcome to have your phone out because you’ll play worse and I’ll win. But poker is an opportunity for people to get together and catch up. Unplug from technology and work to spend this time with people who you enjoy. The point is to slow down and talk about life.

Step No. 3: Have a Great Cigar in Hand

Light that cigar up! You’re forced to slow down smoking a good cigar since it takes you about 45 minutes. Card games go back a long, long time, much like cigars, so a cigar reflecting old nobility like Highclere, a super-premium brand, plays on the entire aesthetic.

Step No. 4:  Prepare a Rich Spread

When I do a poker night, I like to go all out. Prepare a great spread of food like charcuterie and great cheeses. Make it a low-key, yet fancy occasion, especially if you’re in a space that speaks well to that. Women tend to be better at planning parties or events, but guys appreciate you creating an experience. Then you’ve raised the bar for the rest of your buddies who think when it’s their turn hosting, “Let me go to the Italian meat shop for better soppressata and prosciutto.”

Step No. 5: Add Whiskey

A great whiskey or gin and tonic pair really well with a high-class cigar. I’m more of a scotch guy, but bourbons, the sweetness, pair great. Adding a great drink speaks to the relaxation of the event, which is meant to be an excuse to unplug.

Step No. 6: Invest in Real Chips

Little details, from the aesthetic point-of-view, make the whole experience more authentic and enjoyable. You want the real clay chips — the way they feel on your hand and the sound they make. It feels like you’re playing for real and there’s a vibe to that. Other than investing in heavy, professional-grade chips, do the same with the cards. You’re upping the ante, so to speak.

Step No. 7: Dress Like a Gentleman

The final piece that goes into creating the perfect poker night is asking whether you want to sit there in a ripped T-shirt and sandals. I tend to say at a cigar lounge or club, it’s typical to at least wear a jacket, not necessarily a tie. If you’re trying to craft a gentleman’s experience, I recommend a smoking jacket. A fun, red velvet jacket is a preference of mine, with no tie.