Tony Spilotro's Outfit Predecessor Tied To Ice Pick Torture Murder Of Beautiful Cocktail Waitress

Tony Spilotro was sent by the Chicago Outfit to oversee their interests in Las Vegas, and was the inspiration for the Joe Pesci character in Martin Scorsese's Casino.


Spilotro protected the Outfit's money, aka the skim (illegal casino profits "skimmed” off the top).

Because the Outfit 's interests in Las Vegas predate Spilotro, before Tony the Ant, another mobster terrified people on the fabled Las Vegas strip (as well as in Chicago and elsewhere). Marshall Caifano was sent to Las Vegas to purchase land but also looked out for the Outfit's interests, which included the Riviera casino then run by Gus Greenbaum, formerly of the Flamingo. Caifano was a suspect in numerous unsolved murders, typically involving Outfit associates. He was also suspected of committing the notorious, grizzly murder of Estelle Carey, a beautiful young cocktail waitress. One of the perceived motives for the killing is that she was "made an example of" to keep her Outfit-connected nightclub owner boyfriend quiet about a lucrative extortion racket involving Hollywood studios.

Caifano, a former boxer with a cauliflower ear, barely stood 5 feet tall. (Spilotro also only stood a couple of inches over 5 feet.) Caifano's colleague Vincent the Saint  Inserro (who was a mentor to a young Anthony Spilotro) also was of short stature. "If one stood on the other's shoulders, they might have been able to change a light bulb," it was said of them.

Caifano, who cited his Fifth Amendment right 73 times before the McClellan Committee, came up under Samuel (or Salvatore) "Sam" Battaglia, a powerful Outfit boss and such a massive earner, it's almost inconceivable. Battaglia--who had three brothers, all criminals -- was called Teets. There's 25 different stories as to how he got the nickname but my favorite: he once told another wiseguy: "Shaddup, or I'll bust you in da teets."

Sam  Teets Battaglia

Some of the Outfit's largest icons had been in Battaglia's crew. Aside from Caifano, crew members included Albert "Obbie" Frabotta, Felix Anthony "Milwaukee Phil" Alderisio, and Jackie "The Lacky" Cerone all were with Battaglia. Then there's the "42" connection: With Sam (Mooney) Giancana's rise in the Outfit came the elevation of his crew, many of whom had been together in the old 42 Gang: Sam Battaglia, Felix Alderisio, Marshall Caifano, Jackie Cerone, and Butch Blasi, among others.

Battaglia later replaced Giancana as "don" of the Chicago outfit in 1965. (Though of course backstage, Antonio Joseph Accardo was the boss. In fact, Teets didn't want the figurehead job, didn't need it, but he had to take it because that was what Accardo wanted of him.) In June 1966, less than a year after his ascension, Battaglia nearly cracked the entire Chicago Outfit open like a melon when he came dangerously close to going to war with Fifi Buccieri, who'd dared to invade some north side casinos Battaglia's crew operated. Tempers flared and things grew heated, and Accardo and Paul "the Waiter" Ricca, called a meeting to try to get in front of the problem. (Ricca and Accardo ran the Outfit for many decades, beginning in the early 1940s, when Ricca became boss and Accardo underboss.  Accardo held power until his 1992 death.) Then during the meeting, things worsened when underboss Joe Ferriola seemed to side with Buccieri, prompting Milwaukee Phil Alderisio to leap across the table at him yelling, "I'll tear you apart!"

The tension continued simmering in Chicago as 1966 became 1967, and Battaglia was close to getting a "goodbye" from the boss. Accardo believed Teets, as top man in the organization, and among the wealthiest of the wealthy members, should've been more reasonable and accommodating, supposedly. Then the Feds arrived and decisively ended the internecine strife by indicting Battaglia on extortion and sending him to prison. Battaglia died of cancer in 1973.

Teets brought in such serious cash, Accardo allowed him to assemble a larger crew than was typical. (The secret to Teets' success was his willingness to loanshark in the 1950s, when most Italian gangsters allegedly shunned the business, "more or less leaving it to the Jewish arm of the organization," John William Tuohy wrote on the American Mafia website. I've never heard about Mafia disdain for loan sharking. Loan sharking, gambling are traditional Mafia businesses. I've heard wiseguys get squeamish about prostitution, but collecting a vig?)

Teets' crew made fortunes dumping stolen whiskey into Chicago's bars. They did arson-for-hire jobs. They pooled funds and invested heavily in commercial real estate in Nevada and Arizona, taking ownership of a massive industrial office complex. They also owned car leasing companies, laundries, hotels, motels, resorts trucking, building supplies wholesale companies, clothing factories, food processors, dairy products and theaters.

Tuohy noted that they "made so much money that the entire gang were regular attendants at the stockholders meeting of the giant Twin Foods conglomerate. A company spokesman later identified four of the gangsters in Battaglia's crew as paid salesmen for the company."

Battaglia and Caifano went back to the storied 42 gang, the street gang/farm team for the Mafia that both had belonged to in their early years.  Once they were even arrested together. On August 18, 1943, the police pulled them over, searched the vehicle, and found a sawed off shotgun, a rifle, a hand grenade, and five pistols. Battaglia said he didn't know nuttin and since the car was a rental, the case was dropped. The lesson wasn't: From that day forth not a single ranking member of the Outfit ever rode around in a car that they owned outright on paper.

It was Battaglia who sent crew member Caifano to Las Vegas with "a boat load of cash" to invest in real estate surrounding the casinos on the strip.

Grizzly Murder of Estelle Carey
Caifano was connected to the murder of Estelle Carey, a plucky cocktail waitress who was romantically involved with high-profile, Outfit-connected nightclub owner Nick Circella. 

Estelle Carey in her prime.

Nicholas Deani Circella, aka Nick Circella or Nick Dean, arrived in the US in 1902, and by the 1930s, was a nightclub owner with ties to the Outfit. According to the blog Chicago Crime Scenes, at Circella's 100 Club, Circella and others learned that a group was extorting the Balaban and Katz theater chain when one of the extorters stumbled into Circella's club drunk and simply told them about it. Circella and others, with the Oufit behind them, then appropriated the scheme, which involved the extortion of huge sums of money from movie companies through control of motion picture industry unions. It would blow up in their faces in 1943, causing Outfit boss Frank "the Enforcer" Nitti to commit suicide.

Chicago Crime Scenes offers color about the relationship between Estelle and Circella, who "was impressed with Carey’s beauty and offered her a raise to work in one of his clubs as a dice girl. She accepted and was installed at the Colony Club, 744 N. Rush St., where she specialized in “26”. In the game of 26, a pretty girl rolled a series of 10 dice; if the sum of the dice came to 26, the player won a free drink on the house.

"Carey became very popular at the club, and when a high roller showed up, she was often called into work to assist. Not all of the dice games she ran were mere bar diversions like 26, though. One inveterate gambler at the club, who went by the name “Spinach,” claimed she had bilked him for $800 with a die which had the one-spot replaced by an extra five-spot. Other Colony regulars noted that Carey was especially skilled at switching dice with hidden loaded dice."


Carey was known to store a fortune in her closet, also later deemed a possible motive for her killing. Circella bought her expensive jewelry, fur coats, pricey dresses. (After her murder, police who searched the closet revealed that not a single dress cost less than $150, which is about $1,800 in today’s money.)

The IRS was pressing the case and had sought Circella as a material witness. Initially, Circella and Carey lammed it together, with Carey dyeing her blonde hair black. Circella was finally nabbed in March, 1942 and would spend six years in prison for the scheme.

Carey, described by Russo as a "talented nightclub hostess," dyed her hair again, red, and went into hiding. She stayed with a roommate named Maxine Buturff. On Feb. 2, 1943, after her roommate went to work, Carey had a visitor who attacked her after she let him in. A downstairs neighbor later called the fire department when she smelled smoke at around 3 pm. Police later revealed that the killer had not only murdered Estelle, but had tortured her too: He tied her to a chair, tortured her with an ice pick, then doused her in gasoline and set her afire.

Police initially suspected a mob hit but were unable to learn why Carey would feel threatened by gangsters who at the time were known to live and die by a well-known code that specifically prohibited terrorizing women. (It's quite amazing how women seemed to be continually murdered by the Outfit. And using an ice pick on a person is the Outfit's MO. In fact, the more one studies the Outfit, the clearer it seems they were responsible for the Carey murder. Unlike with the five families in New York, where a bullet to the head was sufficient, the Outfit seemed to stage its hits as grizzly set pieces. Again, the Outfit never hesitated to kill women, either.)

Pic from Chicago Crime Scenes

"Like most other Chicago murders of the era, Carey’s would go unsolved, allowing speculation to fill the void. One theory holds that Carey had been two-timing Circella and had divulged his hideout to authorities; another view maintains that both Circella and Carey had skimmed from the Outfit’s Hollywood extortion operation and thus courted punishment; another hypothesis postulates that the Outfit killed Carey to dissuade the defendants from entertaining the notion of testifying against the bosses; lastly, there remains the possibility that the crime was just a ghastly coincidence, having nothing to do with the Outfit or the Hollywood trial. 

"This last possibility certainly jibes with the Outfit’s aversion to involving women in its affairs. It is widely believed in Chicago that Carey was seeing Outfit enforcer Marshall Caifano on the side, and that she was using her cachet with him to manipulate, and infuriate, countless creditors. ...."

The murder of Carey, combined with seemingly related death threats made later, convinced Circella and anyone else to keep their mouths shut. "If Nick Circella had seriously entertained the thought of singing to the G, he quickly thought better of it after the slaughter on Addison Street."

“As soon as [Carey] was killed, that was the end of it,” a prosecutor said. “[Circella] turned off, boom, just like an electric light.” Unlike Circella, Willie Bioff, fearing for his beloved Laurie and their children, reacted with rage, saying, “While we do time for them, they are murdering our families."

 Bioff also testified against the Outfit.

The Writers of Wrongs blog noted that Bioff "betrayed his underworld colleagues and provided evidence to investigators. He confessed that he had arranged annual studio payments ranging from $25,000 to $50,000, depending on the size of the studio, and revealed that the racket was directed by a group of crime figures." He and another were released in 1944 but were both marked men in Chicago.

 Bioff's grand jury testimony brought down indictments against Nitti, Charles "Cherry Nose" Gioe, Frank "Frankie Diamond" Maritote, Johnny Roselli, Louis "Little New York" Campagna, Ricca, Phil D'Andrea and Ralph Pierce of the Oufit,  and an IATSE business  agent.

On March 19, 1943, Nitti, "friend and staunch defender of Bioff to that time," turned a gun on  himself. 

The Riviera
In 1955, Caifano, aka John Marshall, was in Las Vegas to do what Spilotro would later be doing. Caifano was keeping an eye on the Outfit's investment. In 1955, that investment was the Outfit's initial foray into Las Vegas, the funding of the Riviera. While at the Riviera, Caifano recognized someone from his past and wasn't pleased. The man, who was actually working for the Riviera, was none other than Bioff. Since the Hollywood extortion ring, Bioff was living with his wife in hiding in Arizona under her maiden name, Nelson, when Greenbaum quietly hired him to work as entertainment director for the Riviera. (The chapter in Russo's book about Las Vegas is online, read it here.)

Caifano knew instantly who Al Nelson was and  promptly flew home to report to Accardo. Accardo had hired Greenbaum in 1955 to run the casino (and allegedly ordered the murder of Greenbaum's sister-in-law when the wizard of casino management, a heroin addict, hesitated to accept). Greenbaum, in declining health, had just retired from the Flamingo.

Later, after learning what Caifano knew, Accardo told Greenbaum to get rid of Bioff immediately. Greenbaum was later paid a visit by Caifano, who reminded him of Accardo 's edict. "Get rid of that fink or else.”

Tony Accardo, the Big Tuna

Greenbaum, who never seemed to learn a lesson, didn't follow that advice, either. The result was predictable: on November 4, 1955, Willie “Al Nelson” Bioff walked out of his Phoenix home, climbed into his pickup truck, turned the  key and --  BOOM!!! He activated dynamite linked to the ignition.

Greenbaum, shocked by the killing, fell deeper into his addictions. Greenbaum, who took over the Flamingo abruptly after Bugsy Siegel was gunned down in Los Angeles, spent evenings shooting heroin with prostitutes. Only he soon added a new trick to his repertoire, another older addiction, and he began losing stacks of money at the craps tables. Eventually, due to all the drugs and a growing fixation for prostitutes, Greenbaum could only  work a few hours in the afternoon.

From left: Greenbaum, Roselli, Lansky.

The Outfit's bosses were shocked to suddenly learn  the Riviera was losing money.

The next time Caifano dropped by to see Greenbaum, his advice was: "Sell out or you’re gonna be carried out in a box." Afterward, Greenbaum told his staff: “I don’t want to leave. This goddamn town is in my blood. I can’t leave.” On the morning of December 3, 1958, Gus and his wife were both found murdered. Gus, in bed  in his silk pajamas, had been nearly decapitated with a butcher knife. His wife, Bess, was found in the den on a sofa, also with her throat slashed.

Russo writes in The Outfit that the murders may be a result of a certain meeting on Thanksgiving Day in 1958 of the so-called Four Joes. "The site was the Grace Ranch, owned by Detroit gangster Pete “Horse Face” Licavoli. The FBI received reports that Joe Accardo had made the holiday trek to Licavoli’s outpost to confer with New York Commission bosses Joe Profaci and Joe Bonanno and his brother-in-law Joe Magliocco, all of whom had attended Apalachin. With Accardo playing host, the Four Joes feasted on barbecued steak and discussed their business in Sicilian. It was rumored that one of the business decisions they reached cost Joe Accardo $1 million - the money he had lent to Gus Greenbaum for the Flamingo, which could now never be repaid."

Russo also noted that some Chicago insiders, however, believe the murders had been authorized by the front investors in Miami. (Police learned that two men had arrived from Miami the day of the murders and returned to Miami on the night of.)

Backing the Miami theory was a conversation between Roselli and Jimmy Fratianno two years after the murders. Fratianno mentioned the Greenbaum killings, and Roselli said, “That was Meyer’s contract.”

Caifano was the suspect in many other unsolved killings, including the 1950 slaying of former Chicago Police Lt. William Drury, the 1952 strangulation of mobster "Russian Willie" Strauss and the 1973 shotgun killing of disgraced police officer Richard Cain in Rose's sandwich shop on West Grand Avenue. Caifano was a suspect in the murder of oil tycoon Raymond J. Ryan. And the list continues.

"This was a guy who was one of the original [Anthony] Accardo confidants," said Jim Wagner, the former chief of the FBI's organized-crime section. "He was a close friend of Tony's, doing as much heavy work as Accardo or Sam Giancana or anybody."

In March 1980, Caifano was arrested in West Palm Beach for transporting stolen securities from Illinois to Florida in 1975. On May 23, 1980, a federal judge in Miami sentenced Caifano to two concurrent sentences of 20 years at the federal penitentiary in Sandstone, Minnesota. He was released from prison in 1990. He lived into his 90s, dying in 2003 of natural causes.

Casino Mobsters
Tony Spilotro reportedly entered mob life in his early 20s, under the tutelage of Outfit killer "Mad Sam" DeStefano, and went on to work with feared hit man Milwaukee Phil. Spilotro was a suspect in over 20 killings.

By the mid-1970s, he was the outfit's top man in Las Vegas. Over time, he managed to slowly erode the good will of his mob superiors by repeatedly violating rules and running his own gang, the "Hole in the Wall Gang," led by Frank Cullotta. The crew burglarized jewelry stores and robbed and beat gamblers. Spilotro also broke internal mob rule, primarily by screwing around with the wife of Lefty Rosenthal. Mob boss Joey "Doves" Aiuppa was reportedly furious that Spilotro was having an affair with Rosenthal 's wife. (Sharon Stone was perfectly cast, bearing a striking resemblance.) Years earlier, Rosenthal, while a bookie and oddsmaker, reportedly saved Spilotro's life after West Side mob boss Buccieri began strangling Spilotro after he mouthed off.

"I talked Buccieri out of it," Rosenthal told the online gambling magazine He also helped establish Spilotro in Vegas.

Two bodies that were never supposed to be found were found here.

For much of his professional life, the Chicago-born and casino-bred, Rosenthal had been the country's top handicapper. He was one of a handful of men who literally set the line for thousands of bookmakers from coast to coast. During the 1970's, and early eighties, Rosenthal ran four Las Vegas casinos simultaneously, including the world famous Stardust Hotel and Casino. Rosenthal is also credited with creating the first Race & Sportsbook (Parlor) in Las Vegas.

Rosenthal died on Oct. 13, 2008, and was outed as an FBI informant later that same month. (My thanks to Thomas Hunt, one of the country's preeminent mob historians over at the Writers of Wrongs blog, for tweeting something at the perfect time). Columnist Jane Ann Morrison reported in the Las Vegas Review Journal that Rosenthal was an FBI informant, according to three former law enforcement sources "with first-hand knowledge." This confirmed something that was long suspected.

"While Rosenthal was alive, no one would confirm it. Nobody wanted to be the one who got Lefty whacked," Morrison noted.

Rosenthal’s code name was "Achilles," according to one source. Though when he flipped isn't known, she reported that it was before the 1982 bombing of his Cadillac, as per one source. (After the bombing, the FBI tried to persuade him to enter the Witness Protection Program, to no avail.)

Rosenthal was never indicted. Nor did he testify against Midwest mob bosses during the Kansas City trial that ended in convictions, Morrison noted.

The American Mafia website detailed some of Rosenthal's information, as per recently released FBI files. Turns out, Lefty snitched about numerous high-profile gang land murders, including the Giancana and Roselli hits. Rosenthal also helped law enforcement solve the murders of seven burglars linked to the infamous robbery of Accardo’s home.

In the case of Johnny Roselli, the American Mafia site reported that Rosenthal said that Accardo ordered the murder because Roselli had become a "public source of embarrassment to the LCN." Roselli was found floating in a barrel on Dumfoundling Bay near Miami on August 9, 1976. He'd been stabbed and strangled to death. The murder was committed by Outfit hitman Frank Schweihs, Vincent Inserro, and two others who remained unidentified.

The Hole in the Wall Gang began operations because the crew members had to earn while being on-call for Spilotro, who was there as the muscle for Lefty Rosenthal. (The mob doesn't send these guys paychecks.) To facilitate their ability to earn somewhat freely, Cullotta and his crew bribed Las Vegas Metro cops; some decided it was easier to simply look the other way. The robberies increased. In a city built on gambling and tourism, a rise in street crime attracts a lot of attention.

The FBI was all over Spilotro by the time of the darkly comical Jerry Lisner hit in October of 1979. Lisner had turned informant. The order went to Cullotta. One night, he entered Lisner's house and shot him in the head twice. Lisner screamed and jumped on Frank and the two of them rolled around. Then Cullotta emptied the .22 caliber into him, but he still didn't go down.

The problem, as Cullotta realized, was that he had used half-charges to lower the volume of the shots. (No silencer-equipped pistol was available.) The depleted gunfire barely penetrated Lisner's skin.

Lefty Rosenthal and wife, Geri.

Luckily for Cullotta, the wheelman waiting outside came in to see what was holding Frank up. In the end, Frank and the wheelman strangled Lisner, bashed his head in and dumped him in the backyard swimming pool -- a quick remedy for destroying trace evidence.

Meanwhile, the Feds went to work, agents installing wiretaps on the phone lines connected to Spilotro's Gold Rush jewelry store.

The technicians accidentally tripped an alarm.

Metro PD showed up but apparently didn't spot the wiretappers on top of the telephone poles. At the time, any of them could have been on the take.

From those wiretaps, the Feds soon heard something that put them into immediate action.

Two Las Vegas Metro cops had walked into the Gold Rush. Detective Sergeants Joe Blasko and Phil Leone first gave Spilotro the names of federal informants, then a list of names of undercover Feds.

The Feds acted swiftly -- both officers were fired and arrested and charged with obstruction and bribery. Both cases were dropped but Metro's reputation was in tatters.

Then John McCarthy was elected Sheriff, and he went to work fixing Metro's reputation through good law enforcement procedure. In fact, he's been historically credited for building the strong reputation Las Vegas has to this day in terms of law enforcement.

McCarthy completely reorganized the police force, promoting committed younger men as well as some outstanding trustworthy members of the old guard.

He named Kent Clifford, 33 at the time, to Commander, in charge of the Metro Police Intelligence Bureau. Clifford, the youngest men ever to hold that rank, cleaned house even further.

Clifford knew the fastest and most effective way to get the mob out of Las Vegas would be to cross one boundary he absolutely couldn't cross.

"We couldn't just shoot them and get it over with," he said.


So he chose what he considered to be the second best course of action: get under Spilotro's skin by magnifying surveillance and acting on even the smallest illegal acts.

"If one of them didn't signal at a turn, they were arrested and their car towed," Clifford said.

That alone could cost a wiseguy up to $3,000. Plus, the inconvenience, the sheer "what-the-fuckery" of it all... Clifford was counting on it to rattle cages.

One day, Metro shot and killed a Spilotro associate.

Spilotro put out contracts on the cops who shot the associate.

And Clifford caught the next flight to Chicago to put them on notice that if they broke the rules, he was going to break some rules, too.

"If you kill my cops, I'm coming back with 40 men and we're gonna kill everything that moves, walks or crawls in your homes," he said he told them. Scott Burnstein, in Family Affair, wrote that Clifford was unable to meet with Joey Doves and Joey the Clown Lombardo, so he'd left messages about a tenfold reprisal with their wives.

 Clifford flew back to Chicago and soon enough, word reached him that Spilotro wanted to meet him alone, face to face.

Spilotro told Clifford that he had gotten him, Spilotro, in a lot of trouble. He also told Clifford that he was crazy to threaten the Outfit bosses.

"They got 400 guns on the street," he told Clifford.

"That makes us even, then. Any one of my men is worth about 10 of yours."

Their bodies were supposed to disappear forever. No bodies, no investigation. But despite all the trouble the Outfit went to having the Spilotro brothers buried in the middle of nowhere (in a cornfield alongside Highway 41 in northwest Indiana), the remains were discovered by a farmer.

Frank Calabrese Jr., in an interview, said the bodies had been found because the men in charge of the burial only dug the graves five feet down, not deep enough,a result of a change the Outfit made in terms of how its crews were historically organized.

In the summer of 2007, during the Family Secrets trial in the downtown Federal courtroom in Oak Park, the June 1986 murders of the Spilotro brothers, Anthony and Michael, were at long last formally detailed in court.

Joey Doves was sent off to prison in the spring of 1986 and was still furious with Spilotro. The boss was going away largely because of testimony by informants who flipped because of Spilotro. He ordered the hits on the brothers, both of whom still faced trial, Tony in both Las Vegas and Chicago.

Nick Calabrese and a hit team of about 10 Outfit killers sprang into action, luring the brothers to a meeting in a house in Bensenville, a village near O'Hare International Airport in DuPage County, Illinois. Tony was getting promoted and Michael was going to become a made member, they were told. Still, they likely knew they were in trouble. Before the brothers left home, Michael told his wife and one other person that if he didn't come back, "It was no good," as per FBI documents.

Calabrese testified that he and the others (the group included James LaPietra, John Fecarotta, John DiFronzo, Sam Carlisi, Louie "The Mooch" Eboli, James Marcello, Louis Marino, Joseph Ferriola, and Ernest "Rocky" Infelice) were in the basement when Tony and Michael walked down.

Calabrese testified that he had tackled Michael and held his legs while someone strangled him with a rope. He heard Tony Spilotro ask, "Can I say a prayer?" There was no reply.

The bodies were driven to the outskirts of Enos, Ind., to a cornfield where Fecarotta and others buried them. On June 23, a farmer found the grave. The bodies were found viciously beaten, covered in bruises from head to toe.

A forensic pathologist testified that autopsies of the Spilotros determined that multiple blunt trauma injuries were delivered to the head, neck and chest. The bruises likely resulted from punches and kicks versus, say, baseball bats. Ultimately, he said the Spilotros died partly because their lungs and airways were so filled with blood, they couldn't breathe.

The Spilotros were denied a Catholic funeral at St. Bernardine in Forest Park because of their organized crime ties. After a private service in a cemetery chapel at Queen of Heaven Cemetery in Hillside, June 27, they were buried in the family plot