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The Chicago Way

The Chicago Way

We drive by convicted racketeer Paul Korluck’s house, check out the place where “Joey the Clown” Lombardo held his fabled high stakes card games with Evel Knievel, and see the site of the Mob hit on compromised cop Richard Cain, aka Richard Scalzitti. 

And we hadn’t even had a cigar yet. 

Welcome to Mike Hammond’s Chicago, a place the retired Chicago PD homicide cop knows well. 

We’re entering what was once known as The Patch, a neighborhood largely populated by Italian immigrants pocked with others from Eastern Europe. Sam Giancana, boss of Chicago’s Outfit, the city’s division of the Italian Mafia, was born in the Patch in 1908 and held sway there for years. 

“There were at one time more mobsters in this area than any other in the city,” says Hammond, who served in the Chicago PD from 1994 to 2016, easing the car across the Chicago River and west down Grand Avenue. 

Hammond is the host and developer of “Detective Story with Mike Hammond,” a podcast that looks at old crimes and cold cases, and dives into the lives of cops and the problems they take home with them, a not-so-lovely byproduct of policing. 

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The trains rattle the floor in the lounge of Iwan Ries & Co.
Photo credit: Iwan Ries

He grew up with cigars, with a grandfather who grew up on a Kentucky tobacco farm. Hammond smoked the occasional cigar over the years but became a self-described “cigar nerd” shortly after he retired. 

“I was smoking good cigars all along,” he says, “but I didn’t know it. I had no idea what I was doing.” 

While the Patch is no more, it casts a formidable true crime shadow. 

“There are still people from the old days that are around,” he says, cruising past Korluck’s a second time. Korluck was sentenced in 2016 to 18 years in prison for racketeering, described in a news story on his crimes as “a leader of a mob-connected crew on the Near West Side.” 

Korluck was paroled in 2022 and returned to his home in the Patch, a smallish brick WWII era place with a sizable side yard that is surrounded by an eight-foot-high wooden fence. 

“Ah, he’s home, there’s his car,” Hammond says looking down an alley behind the corner lot that he and his cop colleagues refer to as “the compound.” 

The settlers of the Patch arrived in the late 1800s, establishing business and a way to ensure law and order in a city that was already bustling with scams and grift. 

It blossomed into a haven of organized crime activity, with flower shops, restaurants, bars and of course, social clubs. 

Cops were at one point rarely needed. There was a cigar place in the Patch a couple decades back and someone got the bright idea to burgle the place. 

“They got into the safe, plus they got cigars,” Hammond says. Turns out the place was connected to, or at least friendly with, Lombardo. 

“They put word out pretty quickly, and it was kids connected to [the heist],” Hammond says. “It’s a good thing, because anyone else would have been in pretty rough shape. Instead, they begged for mercy and returned it all.” 

That was the lightweight stuff, though. The Patch was usually heavier. 

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Mike Hammond’s podcast highlights some of the crimes he worked as a Chicago PD homicide detective

Richard Cain, a former Chicago cop, was also a running buddy of Giancana, serving as a bagman between the Outfit and dirty cops. When he got sideways with the Outfit in 1973, Cain was murdered during lunch hour in a sandwich shop in the Patch. 

We cruise by a relic, the Huron SAC (Sport Athletic Club) on Huron Avenue. It was once littered with wise guys but is now just part of the neighborhood’s residential offerings, with an upstairs apartment listed for $1,500 a month. 

Five blocks south is the site of a double homicide in 1988 that stemmed from a Mob-related drug dispute. Hammond went to the state prison a couple times to talk with one of the convicted and sentenced to life, Joey Bravieri, as he tracked down leads on other cases. 

“I was fishing,” Hammond says. “But he didn’t want to talk about murder.” 

After a few passes through the Patch, Hammond pointing out more sites, it’s clear the neighborhood remains unique amidst the clamor of urban Chicago: No hipsters. It’s a man-bun free zone, no ironic fedoras allowed and the only tattoos to be seen are a faded blue, as prison ink isn’t nearly as effective as the stuff today’s college kids are privy to. 

“The crime was all insider stuff, pretty much,” Hammond says. When Outfit boss Joe Lombardo held card games, motorcycle daredevil Knievel was among the honored guests. It was the safest place in town, Hammond says. 

We ease past storefronts, some revamped, others sticking with their vowel-laden names. At an angled corner, Richard’s Bar sits, a beacon for those invested in Mob watching. The place for years has been rumored to draw a dinosaur from that era – with weed and gambling mostly legal now, mobsters are a dying breed. Even lacking a wise guy sighting, the place is a dumpy looking, charismatic reminder of the old days. 

And while the city mostly revels in a non-smoking posture, word is that you can smoke AND buy a drink in Richard’s, cigars and cigarettes. 

Unspoken is a good thing here. 

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The humidor at Norwood Royal Cigars, a reliable stop in and out of O’Hare Airport
Photo credit: Norwood Royal Cigars

The City Is Still a Cultural Cauldron

Despite this dark intro to what is in the dozens of Chicago visits over the years, the town remains “stormy, husky, [and] brawling,” as poet and journalist Carl Sandburg described it. The accent is brusque, the pace fast and it’s a good idea to stay in your lane. The city remains culturally splendid. There are professional duty sports venues in every direction, a world-class orchestra, museums that rival New York’s, and a thriving culinary scene. 

The city has in the past several years had an alarming street crime problem, which the city has wisely addressed by dispatching teams of beat cops to walk the most popular areas. That means a walk down Miracle Mile, a teeming stretch of luxury stores and hotels, is a little safer than just four years ago, when rampaging youths targeted blissfully unaware tourists. 

We head to Old Town and Up Down Cigar, a block from The Second City, the improv comedy theater that counts local heroes Bill Murray and John Belushi among its alums. 

Up Down is imposing and welcoming, a jammed space with a humidor and accessories cases that curl around a main social area. The counter has six seats and just a few customers create a packed house, but the displays of cigars and accessories are easy to navigate. 

Up Down’s founder Diana Silvius, who died in 2016, was a visionary as she developed the space, which started in a spot around the corner as an art gallery with cigars on the side.

When she went all-in on cigars, Silvius launched as a dedicated cigar store, taking its present location in 1976. 

We head out back to a tented area, which features picnic benches and several large TVs. It’s heated in the winter – “gets up to around 55 or 60 degrees,” says Joel Krakow, a tobacconist at Up Down. That’s balmy in a Chicago winter; you’ve been warned. 

Up Down is a feast for the eye, with cases filled with lighters and humidors in addition to cigars, so it’s easy to miss the art that rings a short upper level to the main room. It’s adorned with metal work that is designed to look like wafting smoke, and several cigar store Indians sit among the twisted steel. One can be yours for $2,000, Krakow says. 

Up Down was a place of few rules in a city and state that is run by a few people that dislike smokers. Sadly, those few people also like to make rules and the impact on cigars is noticeable. 

First, there can be no alcohol served in a place with smoking, although you can bring whatever you need and some places provide ice and mixers. Wholesale cigars are hit with a 36 percent levy – so a $15 cigar becomes a $20.40 cigar before the 9.25% state sales tax. Annoying? Sure is. 

This draconian approach to taxation has caused the demise of several cigar stores since Cigar Snob’s last visit to the city in 2013. There are other laws that can be obstacles – membership fees at some, no smoking on premises at others. But the strong have survived, keeping prices sane and creating welcoming spaces. 

We head over to one of the newest cigar places in the city that is bringing the experience to a new level, The Clayton. 

It sits on a triangle-shaped corner that opened in 2016, two blocks from the city’s restaurant row, a series of foodie, upscale restaurants. While the façade is inviting – tall glass windows with plenty of light beaming into a space that could double as a living room – the spread inside is four stories of members-only luxury, plus a front retail and lounge area with 20 chairs. 

The front room is fine for drop-ins, though, with a $20 membership fee that is taken care of with the purchase of a cigar. Buy a cigar from the well-appointed, medium-sized humidor, and grab a seat. It’s quiet and comfortable with the original brick walls, tile floor and televisions. On our visit, a priest sat with a businessman, animatedly talking national politics. 

But upstairs, it’s so much more. Each floor has carefully curated rooms, with couches and chairs meltingly beckoning. Its members, though, are a carefully guarded secret, as is the membership fee. If you have to ask, you probably can’t afford it. Its membership roster is full at 350 smokers. It’s so private that even checking out its Instagram portal requires approval.

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The retail space at Iwan Ries
Photo credit: Iwan Ries

“We like people who are interested to come in and get a tour, see what they are getting first,” says Clay Wilson, founder of The Clayton. He opened the place after seeing that the area had more demand than supply in terms of luxury cigar experiences. 

“And I saw that when winter weather is in full force, there is nowhere to go so people typically either smoke at home or don’t smoke,” Wilson says. The Clayton’s members are “busy golfing or out on their boats in the summer, so our busy season starts Sept. 1.” 

It’s an exclusive enclave of privilege, noting in its promo materials that it’s a “hideaway for the discerning connoisseur.” It is popular enough that The Clayton’s 300 lockers are mostly taken. And while they can’t provide booze and BYOB is not allowed, The Clayton owns an adjoining liquor store that will gladly sell to a Clayton assistant and deliver right to your glass. It offers a selection of bourbons and whiskies along with beer and wine. 

The refined accommodations are a throwback to the blueblood opulence afforded to royalty. They better be; The Clayton this summer opened a location in Washington D.C., a place where your campaign donations will no doubt fund a membership. A Miami location is under construction and scheduled to open in 2027. 

Returning to the Snob headquarters, the Thompson Chicago Hotel, is a welcome break but the halt of the day’s excitement is abrupt. The lodging is a fine place, and we welcome our top-floor room, 2112, just below the penthouse. The Hyatt property is in the middle of the tourist action of Rush Street, and that evening, a storm rushes through, blasting lightning on the western horizon. It’s the perfect antidote to the day’s head-swimming puzzle: How can so many bureaucrats impede the pleasure of the cigar, something that is so simple in most other places? 

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Up Down’s counter has few seats but the displays of cigars and accessories are easy to navigate.

Durable Cigar Stops

In the morning, we head to Iwan Ries & Co., the nation’s oldest family-owned tobacco establishment. It’s so ancient that one of its first stores was wiped out by the Chicago Fire in 1871 after opening in 1857. Photos inside Iwan show the carriage crowd on Clark Street, outside the tobacconist’s early location. 

The lounge in the second-floor store overlooks the “L,” the city’s mass transit system, and trains clack by the window. The lounge requires a $20 day pass during the summer, moving to $25 for the winter. Memberships are $1,000 a year and if you hit the lounge with a member, guest passes are $7.50. 

The store looks its age, in a good way. Like Up Down, it’s a circus of memorabilia, with posters, old cigar presses, a boxing glove signed by Larry Holmes and some dust. Hanging over the store are two vintage chandeliers, with a couple more in the lounge space. 

Plus, pipes. 

“We are split about 50-50 between pipe and cigar customers,” says Kevin Levi, general manager and part of the fifth generation of the Levi family to operate the store. He said the humidor sticks with the top sellers, “mostly because that’s what everyone wants here. We have people calling for Padrón all the time, things like that. Our customer base is very traditional, it’s a downtown crowd.” 

So expect plenty of Plasencia, J.C. Newman, Davidoff and a very traditional, wood-paneled lounge to enjoy them in. The lounge has expanded from one to two large rooms, a testament to the coziness and the comfort of the place. While the sunny summer was in full swing, there’s something alluring about looking out those big windows at the dark night with the snow flying. 

Most travel into the city starts with Chicago O’Hare International Airport, which ranked ninth in passenger traffic in the world last year. Some hate the place, but we’ve always enjoyed it. And to make the move to and from the city easier, there is Norwood Royal Cigars, a shop that sits three minutes off Interstate 90 and seven miles from the airport. 

Owner Vick Shah has operated cigar stores for 22 years, nine at the current location. The substantial humidor alone takes up 1,500 of the 3,000 square feet of his retail storefront, a massive but tidy display featuring 7,000 facings. 

Anything you could want, from the latest Oliva to an obscure boutique brand, is in there. 

“And people buy everything we have in here,” Shah says. 

Smoking is done on ten lounge chairs on the patio of the store, while members have access to a large, Diamond Crown Lounge next door, outfitted with chairs, televisions and a bar where a tapper of beer is always on hand. 

“I never wanted to have a lounge,” Shah says, but with the patio and the next-door oasis, he has relented somewhat. The venue hosts large sports events for members and Shah regularly has outdoor events featuring food trucks, DJs, and raffles in conjunction with a visiting cigar celebrity. 

Shah also offers 10 percent discounts to police, fire and military members, which compose around half his regular clientele. It’s handy for them, as the neighborhood around Norwood Royal is an area where a lot of fire and police live; Hammond himself once had a place nearby. 

The discount stems from his father’s insistence that Shah as a youth become a police officer in his native India. 

“I went to training for two days and I left,” he says. “But I gained great respect for them from that and that’s where the discount comes from.” 

We wheel out of Norwood and head back south toward downtown cutting through the city, and see a gentle reminder of another famous Chicago feature – food. 

The reminder is two giant ceramic hot dogs extending from the roof of Superdawg, a drive-in so old school it would have been at home in the Flintstones. 

The tube steak is a culinary masterpiece for many Chicagoans, an answer to the upscale dining that is part of the city’s fabric. The place has a menu but don’t bother – get the Superdawg, on a poppy seed bun with mustard, pickle, onions and hot pepper. 

Of food, Chicago is full of it. We had dined after our venture to The Clayton, where Vick provided one of his in-house cigars produced by Oscar Valladares, at Club Lago, an Italian joint that is run by third-generation family members GianCarlo and Guido. The place is like a movie set for a Mobster flick set in the 60s, featuring a tin ceiling, terrazzo floor and an actual cash register. 

On our introduction by Hammond, GianCarlo started telling his own tales of cigar smoking, how it used to be so much easier in Chicago to just smoke and suddenly, he pointed to a large wooden replica of the White House. 

“You know what this is?!” he exclaimed, as if he just remembered it was there. 

Without waiting for a response – “a cake?” “a tank?” – he opened the lid. It was a humidor, and a well-crafted piece to boot. 

We washed the day away with some splits of house Chianti, some pasta galassini, and some meatballs. 

Coming back from Royal Cigars, it was time to hit the city’s Greektown. While it can’t measure up to Detroit’s Greektown, Chicago’s version can bring a formidable feast if only because of Greek Isles, a locals/tourist restaurant. 

It’s a white tablecloth place, spacious and loud. There’s a nice long bar in a room off the main dining area that features a look onto busy Halstead Street, which goes well with a glass of Maleatis Agiorgitico, a Greek red.

Chicago Prevails Despite Best Efforts to Sink It

The City of Chicago has been plagued for decades by shoddy management and if it were a for-profit venture, it would have gone under long ago. But despite the decisions that marginalize the city and its residents, the people win. 

These shop owners, not just the gracious managers we talked to but also those in the region we didn’t get to, are masters and survivors. They have navigated onerous tobacco laws to ensure their customers have something good to smoke and a place to do it in relative comfort. 

Visiting these places was inspiring as were some of the patrons we spoke to. They take what poor policy their elected officials, both state and local, give them and make the best of it. Some restaurants keep their humidors filled, like relics from a bygone era. Used to be that a post-dinner cigar was the rule in the city. 

At Iwan Ries, they coped with the no smoking law that took effect in January 2008 – covering all bars and restaurants – by opening another room in the lounge, hoping to make up for the loss of sales to local restaurants. It worked, kinda. 

“That was a big hit, we supplied all the local restaurants, but we made it,” said Levi of Iwan Ries. “We were the first lounge to open on the heels of the ban.” 

Tenacity and imagination work and even the slimiest, most meddling bureaucrat can’t defeat them. 

Chicago came back with gusto after the fire of 1871 took out a third of the city. 

Today, against the odds, it’s putting fire to cigars. 


This article appeared in the September/October 2024 issue. Subscribe today to get the magazine in your mailbox.

Click HERE for more stories!

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