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Thirteen years ago, during my second trip as an adult to that star-spew oasis in the armpit of the desert known as Las Vegas, I got stuck on a monorail. On this particular August night, a wicked storm was wreaking havoc along the famous Strip, with flash floods sending confused waves onto the sidewalk and into our shoes. My wife and I were en route from the Motown Café at the New York New York resort (we’re suckers for singing waitresses) to the Flamingo. The monorail in question ran between the Monte Carlo and Bellagio hotels – it’s still there, except now it passes through the monstrous City Center complex along the way. When we got stuck, there was nothing but a parking lot some fifty feet below us.

I wasn’t worried. The angry rain was kept at bay, and besides, I had a plastic football filled with delicious ale from the little brewery in the basement of the Monte Carlo.

Much more fun when it's full.

Much more fun when it’s full.

And besides, after we’d leapt from our car to the back-up monorail on the other track, I was sure someone would be waiting to greet us at the Bellagio, handing out a small stack of chips or a pair of complimentary show tickets for our troubles.

I was wrong. Mob-era Vegas was over. 2000 was taint-deep in the corporate era, and while they took down our information, they had no intention of compensating us for the hour of further intoxication we’d lost.

Las Vegas was built on a foundation of mob-money. Even though the family-friendly resorts of modern Vegas do their best to come across as honest, considerate corporate entities (so… people, technically), most of them hide a dark secret. It’s Vegas – you should probably try to stay somewhere with a dark secret or two. It’s more fun that way.

Flamingo

While not the first Vegas casino to be mafia-run (Chicago had its hand in the city’s back pockets since gambling was legalized in Nevada in 1931), the Flamingo was an ambitious endeavor. In 1945, Chicago mobster and future Boardwalk Empire star Bugsy Siegel bought the land from Los Angeles club owner Billy Wilkerson, with dreams of cashing in on the steady traffic along Highway 91. His $1 million hotel more than quintupled in cost though, which didn’t sit well with his bosses.

Like all Vegas hotels, the Flamingo changed hands several times, landing under the influence of Miami-based mobsters in 1960. Kirk Kirkorian, the guy who hand-picked the land which would come to be Caesar’s Palace and the original MGM Grand, bought the place in 1967, eventually selling it to the Hilton Corporation. So the Flamingo, born of the mob, has been mob-free for about 46 years.

Tropicana

I’ve never stayed at the Tropicana, nor have I even set foot inside the place. That’s because the Trop is one of the last pure Vegas hotels on the Strip. They’ve got a casino, some hotel rooms, and few venues for shows, but they haven’t succumbed to the pressure of amusement park rides, super-niche themes or majestic themed pool areas, all of which are located at hotels literally right across the street. If you want to hit Vegas for straight-up craps, this is your place. If you want some mob history in your stay, well this will also work.

Phil Kastel was the first to run the Tropicana after its 1957 opening. The Gaming Control Board had a hunch Phil was mixed up with a bad crowd, and when the hotel’s earning figures were found on a note in mobster Frank Costello’s pocket, it didn’t look good for Phil. He had to sell. A club owner, an airline, and a chemical fortune heiress took turns with their names on the Tropicana deed, but the hotel never really matched up to the hotbed of activity going on a few blocks to the north. In the late 70’s, their only company around Tropicana Avenue was the bland Marina Hotel across the street and the Hacienda down the road. In 1979 a money-skimming operation at the Trop was linked to the Kansas City mafia, enabling a quick sale to the Ramada Corporation.

Hacienda

The Hacienda had to wait a while before getting their hands dirty. At the southern edge of the Strip, this resort had the benefit of being so far away from any other casino, most of its guests never bothered venturing off the property. They were, however, close to the airport (Mandalay Bay now sits on this slab of land), and they had their own airline with which they could jet in high-stakes gamblers from wherever.

The Hacienda opened in 1956. It wasn’t until it was sold in 1972 to Allen R. Glick that the tentacles of organized crime began wrapping themselves around the count-room. The Circus Circus people bought out the resort in 1995 and blew it into dust. After that, the mob didn’t have much interest in the place.

Sands

While I couldn’t find any information indicating that the Sands – upon whose shimmering bones the Venetian now rests – was ever run by gangsters, I’ve got a hunch something was up. Come on, Frank Sinatra was a regular performer there. Frank knew which side of his toast was lathered up with organized crime-butter. ‘Nuff said.

DesertInn

When Wilbur Clark set out to build the Desert Inn, he had noble intentions, probably of rolling around naked in tourist dollars. Problem is, he ran out of money during construction. Moe Dalitz, Cleveland mobster, was happy to help out. The Cleveland syndicate kept things rolling from the hotel’s opening in 1950 until Howard Hughes dropped in and booked the top two floors in late 1966.

Hughes didn’t want to leave, and negotiated to buy the place the following year, transferring ownership from the crooked to the bat-shit insane. The building is ancient history now (of course), with the Wynn taking up its space.

Stardust

The Stardust. Now home of the nothing. I wrote about it yesterday – you can read that article, or better still, you could rent Casino and check out all the criminal goings-on of that joint.

Dunes

The Dunes, whose hotel, casino and parking lot could all fit inside the Bellagio fountains (which is, technically, where they were), was tied in with organized crime right from the start. Financing came from the Teamsters, from Hollywood, and reportedly from a Rhode Island crime syndicate. When the resort hit hard times in 1956 (a year after it opened), the Chicago underworld bought in and saved the day.

In the 1960’s, Morris Shenker bought an interest in the Dunes. Shenker was on the St. Louis Commission on Crime and Law Enforcement, but he was also tied to the local underworld. Hey, he was Jimmy Hoffa’s chief council. He kept the gangster vibe in Vegas right up to its sale to a Japanese investor in 1987.

There wasn’t a lot left for the mob once the corporations took over. Now Vegas is glitzier, flashier, and packed with a lot more to do other than drinking and gambling. But in the process, the town has lost a bit of its charm.

And really, one guy in a suit, handing out buffet tickets to the folks who were stranded on the monorail, that would have happened back in the mob’s Vegas.