Carmen Milano: Attorney, Underboss, Flipper

Anthony (L) and Carmen Milano (R)

“Flipper! Pete Milano’s younger grubby brother who became underboss. Carmen was actually the tougher of the two, and he had the connections back East. He just had no luck. I guess he should have stayed in Ohio. He was a lawyer!”

– Kenny “Kenji” Gallo, former Los Angeles associate

Like his brothers, Carmen Joseph Milano was from Cleveland. Born on the 27th of July, 1929, his father was Anthony Milano, known as the “Old Man”, a long-time underboss for the Cleveland family. His uncle, Frank, had been the Cleveland boss during the mid-1930s before fleeing out West, in order to avoid charges related to tax evasion. The older Milano brothers were very well-connected to labour leaders and other La Cosa Nostra (LCN) bosses – individuals like Jackie Presser, Frank “Fitz” Fitzsimmons and Santo Trafficante Jnr to name a few. Carmen Milano, along with brothers Peter, John and Frank moved to California sometime in the late 1930s or early 1940s. Residing in Beverly Hills, he completed high school and then later attended Loyola Marymount University, pursuing a law degree. Anthony Milano divided his time between Los Angeles, Las Vegas and Ohio. As a side note, Milano’s street moniker, “Flipper”, was after the TV dolphin. It is unclear why Milano was called this, though he did not seem opposed to the name, as evidenced by his introduction to Craig Anthony Fiato.

Admitted to the State Bar of California on the 5th of January, 1955, Milano sometime thereafter moved back to Cleveland, while Peter (seemingly John and Frank as well), remained in California. Peter Milano, by this point, had already been involved in Mickey Cohen’s gambling operations and was on his way to becoming a member of the Los Angeles family. The other Milano brothers were minimally involved with organised crime.  

Sometime during the 1950s (or potentially early 1960s), Milano married Pauline Randazzo, the daughter of Cleveland family member Stefano “Steve Rand” Randazzo. Operating out of Florida, in the Miami Beach area, Randazzo may have actually switched membership from Cleveland to the Trafficante family, as he served as Santo Trafficante Jnr’s personal driver, while also accompanying him to Tampa on several occasions. In an interview with the FBI, dated September 7th, 1962, Randazzo claimed that he was suffering financially and that Carmen Milano, along with another son-in-law, Vincent Amato (a Gambino member married to another of his daughters, Jean), were assisting him with funds.

Milano, along with his brother Peter and Dominick Lonardo (seemingly the brother of Big Ange), accompanied Randazzo on a trip to Havana, Cuba during late October of 1958. They were spotted by a Havana-based FBI informant in a casino operating out of Hotel Nacional. Also present in the Hotel Nacional at this time were Trafficante members James Costa “Jimmy” Longo, Salvatore “Sam” Trafficante (brother of Santo Jnr) and associate John Demmi, though the informant does not note any interaction between the groups. The Milano-Lonardo-Randazzo party was present in Cuba until sometime in November. Steve Randazzo would die in 1981, aged 80 – though this was not the only occasion in which the Milano family would be linked with the Trafficante mob.

Alfred “Allie” Calabrese (L) and Carmen Milano (R)

Back in Cleveland, Carmen Milano associated with various underworld figures, both LCN and independent. In the early 1960s, he was a person of interest in an FBI investigation related to a loan of thirty-five thousand dollars from businessman Edward J. De Bartolo Snr (of San Francisco 49ers fame) to Cleveland mob associate Dominic Bartone, who was connected to Nunzio Louis “Babe” Triscaro, a close associate of Jimmy Hoffa. Milano was also linked to Eileen Reddon aka Eileen “Bunny” Curry, a troublesome madam that operated brothels in California, Chicago and Ohio.

The FBI was advised by local law enforcement in Cleveland that a “lawyer friend” had visited Reddon several times during her incarceration in a Warrensville facility, surmising that it was Milano. Reddon seemingly met Carmen while running a brothel in California some years before and boasted that they had planned to hold an intimate meeting at a hotel in Warrensville Heights, on the 19th of March, 1960. Additionally, they were partners in a night club in Geneva, Ohio, called Chatter Box. The pair employed several “confirmed lesbians” as prostitutes, per the FBI.

As mentioned before, Anthony Milano was well connected to Teamster officials and as such, among Carmen Milano’s other dealings with the Cleveland mob, he was held on retainer by Locals 410 and 436, despite effectively rendering no services for these unions. Local 410 represented vending machine employees and Local 436 was primarily concerned with the construction industry, though only the latter appears to still be functional. Of note is that the infamous John Nardi, a cousin of Milano’s, was secretary-treasurer of Local 410. Another Nardi brother, Nicholas Anthony (1926-2014), was also connected to the Teamsters (primarily Local 416) and would be identified as an associate of both the Cleveland and Los Angeles families.

During early September of 1966, Carmen’s cousin, Peter Frank Milano (not to be confused with Peter John Milano, Carmen’s brother and future Los Angeles boss), who seemingly was never made, met with Santo Trafficante in order to ask for assistance with “handling” Cuban pesos. Trafficante refused, citing that there would “difficulty within LCN” if he assisted the son of Frank Milano (nee Ciccio). It is not clear what issue existed between Milano and Trafficante but in the ensuing months that followed, the FBI tried to get in contact with Carmen Milano, in an attempt to interview him about his family’s connections to Florida. However, after several attempts, the Cleveland FBI office reported that any further resources assigned to interviewing Milano would be unproductive.

As the 1960s began to pass by, Peter John Milano, Carmen’s older brother, lost his wife in a mudslide in January of 1969, due to extreme weather conditions in the Los Angeles area. At the funeral, held on the 29th of the same month, Carmen Milano notably was not present. As described by an FBI source out of San Diego (likely long-time LA member Frank “Bomp” Bompensiero), in attendance were the following mobsters:

  • Nicolo “Nick” Licata – LA boss
  • Joseph “Joe Dip” Dippolito – LA underboss
  • James “Jim” Regace (Dominic Brooklier) – LA caporegime
  • Frank “Frank Muscatel” Gruttadauria – LA member  
  • Peter John Milano – LA associate
  • Anthony “Tony” Milano – Cleveland underboss
  • Calogero “Leo Lips” Moceri – Cleveland member
  • Frank Angelo Milano – Peter John’s brother
  • Frank Roger Milano – cousin
  • Peter Frank Milano – cousin
  • Unnamed friend of Peter John (potentially Raymond “Rocky” DeRosa)
  • Angelo Polizzi (attended rosary, not funeral) – LA caporegime
Top (L to R): Anthony Milano, Frank Bompensiero, Dominic Brooklier, Nicolo Licata, Peter J. Milano
Bottom (L to R): Frank Gruttadauria, Joseph Dippolito, Calogero Moceri, Angelo Polizzi, Raymond DeRosa

The source also identifies Pete Milano and his friend as proposed members of the LA family, claiming that Licata intended to induct both men. Peter “Pete” Milano would become a member of the family sometime in 1970.

Remaining in Ohio throughout the 1970s, per former bank robber Phil Christopher, Carmen Milano threw lavish parties held at Cleveland’s Italian American Brotherhood Club (IAB), which he also managed, with various different powerhouses in attendance, ranging from mobsters like James “Jack White” Licavoli to labour leaders such as Jackie Presser and even some politicians. However, following a labour case that involved fraudulent compensation claims, Milano was disbarred from practicing law by March of 1979 and according to the State Bar of California, had resigned his license by 6/12/1981 and was awaiting legal charges – charges that seemingly never came.

Carmen Milano, IAB manger

Back in The Golden State, the Los Angeles crime family was under intense pressure by 1981, following Aladena James “Jimmy the Weasel” Fratianno’s testimony that saw the entirety of the family’s administration convicted and sentenced. Among them was Samuel “Sam” Sciortino, Dominic Brooklier’s choice for underboss and an associate of Carmen’s brother, Peter. Sciortino, along with Brooklier, had received 4 years based off Fratianno’s testimony but was facing additional legal trouble. New Orleans family boss, Carlos Marcello, Sciortino’s cousin, one Philip “Phil” Rizzuto and Sciortino himself were indicted on bribery charges.

The trio had attempted to bribe a federal judge in order to gain favourable treatment for Sciortino and his co-defendants. Brooklier’s underboss received an additional 5 years in prison, effectively removing him from the Los Angeles gangland scene as Pete Milano began to move in. Sciortino would be released in 1989, having apparently met former Colombo caporegime Michael Franzese while serving his sentence. Franzese has recently claimed that Sam Sciortino informed him of Marcello’s involvement in the JFK assassination.

L to R: Philip “Phil” Rizzuto, NOLA mobster, Carlos “The Little Man” Marcello, NOLA boss and Samuel “Sam” Sciortino, LA underboss

Further information regarding Milano’s takeover in LA is the testimony of former Cleveland underboss, Angelo “Big Ange” Lonardo, who claimed that Pete Milano had informed the Cleveland family that he was in control of Los Angeles by 1981, though it remains unclear whether this was on an acting basis for the imprisoned Brooklier or if it was a total takeover. Regardless, Pete Milano was now the leader of the remaining California family and over the next few years there would be several changes. Carmen Milano moved to California in 1984 and resided with Luigi “Louie” Gelfuso Jnr, an LA caporegime and close associate of Pete Milano. Kenji Gallo, in Breakshot, claims that Gelfuso, a former bartender for Nick Licata, viewed Pete as his mob idol and was an extremely loyal and trusted subordinate of the older Milano brother. Gelfuso died in October of 2000, shortly after he had lost his son, associate Michael “Mike” Gelfuso, to cancer.  

Dominic “Jimmy Regace” Brooklier would die in prison in July of 1984 and in October of the same year, various members and associates of the LA family were arrested for attempting to take control of bookmaking in Los Angeles – the Milano brothers among those picked up by law enforcement, though neither Carmen nor Peter were charged. The brothers had also allegedly travelled to New York sometime in 1984 to inform The Commission of Pete’s new position, through connections Carmen had from his time in Cleveland. The LA family had taken on several new members by this point, including Milano himself. A full list of who the FBI considered members in 1985 can be viewed at the below link:

FBI’s list of Los Angeles LCN members in 1985

The Milano brothers had avoided serious trouble for now but following the release of Brooklier-era caporegime and Fratianno associate, Michael “Mike Rizzi” Rizzitello, legal complications would again surface. Rizzi’s associates, Craig Anthony “Tony Rome” Fiato, along with his brother, Lawrence, had begun to cooperate with the FBI as confidential informants, recording conversations with various members of the Los Angeles family. This resulted in a sweeping indictment in May of 1987 that saw both Carmen and Pete arrested, along with several other key family members, including caporegimes Jimmy Caci and Louie Gelfuso. Other notable members indicted were Stephen “Stevie the Whale” Cino, Charles “Bobby Milano” Caci, Russell “Rusty” Masetta (son-in-law of Peter Milano) and Rocco “Rocky Bigfoot” Zangari. It should be noted that Rizzitello was also facing legal difficulties at this time.

Sentenced in May of 1988, Peter Milano drew 6 years and Carmen Milano was ordered to serve 6 months of a 2-year sentence, with Jimmy Caci briefly serving as street boss when both brothers were incarcerated.

L to R: LA members, Russell “Russ” Masetta, Carmen “Flipper” Milano and Cleveland union official Nicholas A. “Nick” Nardi (Milano cousin), seemingly pictured at Masetta’s wedding to Milano’s niece, Antoinette

Pete Milano was released in 1991 with Carmen seemingly filling the leadership position while his brother was ‘away’, after Caci began facing his own legal troubles. Notably, Carmen Milano was not necessarily the first choice for acting boss, despite his position. Throughout the late 1970s, following the Bompensiero murder, for which he drove the getaway car, LA’s no. 3 man was Giacchino “Jack” Lo Cicero, a Sicilian who spoke broken English and who had been an associate of Mike Rizzitello. Lo Cicero had initially been identified by law enforcement as a potential interim boss but was ultimately discounted because of his poor health – Jack died in 1990 and was the last known LA consigliere.

“Flipper” Milano would next emerge in Las Vegas, having moved there from Los Angeles sometime in the early 1990s. Like many remaining members at that point, Milanos involvement in organised crime had begun to drop off as both he and the family ranks grew older. Pete Milano’s lackey, Louis “Little Man Louie” Caruso and Jimmy Caci, through acting capo Steve Cino, were active in Las Vegas but had limited interaction with Milano, even though he remained the official underboss. Much of the remaining Vegas rackets by the late 1990s were centred around either Caci’s Buffalo faction or with Herbert “Fat Herbie” Blitzstein, a former Outfit associate that was involved in loansharking.

Louie Caruso and Tommaso “Tommy” Gambino, despite their respective connections (Caruso to Pete Milano and Gambino to his family in New York/Sicily), were not the “major players” for the LA family in Sin City, according to Kenji Gallo. Milano, for his part, became involved with in a fraudulent diamond scheme along with Blitzstein and reputed New England LCN associate Dominic Spinale – in addition to committing food stamp fraud, money laundering and extortion with two undercover FBI agents, “Sonny Blake” and Vincent “Vince” Torrio.

Dominic Spinale

Milano was additionally connected to former Genovese associate and confidential informant, Anthony “Fat Tony” Angioletti, who managed the Sea Breeze Club, a hangout spot for various mobsters, businessmen and other denizens of the local underworld. Another haunt for the Los Angeles underboss was an Italian deli owned by Gambino associate John “Johnny Mash” Mascia Jnr, where he would meet with Jimmy Caci, Stevie Cino and Kenny Gallo. Angioletti would be responsible for introducing undercover FBI agent, Charles “Charlie Marone” Maurer to former Outfit associate, John “Johnny” Branco (nee Giovanni Brancato), leading to further government infiltration of LA’s operations in the area. Branco, at the time, was also an informant.

Carmen Milano

Like many of the Las Vegas-based mobsters tied back to the Los Angeles family, Milano was indicted following the Blitzstein hit in January of 1997. Blitzstein’s murder was carried out by a motley crew of fringe LA/Buffalo LCN associates without any authorisation and the resulting fallout effectively wiped out the remaining active mobsters in Vegas.

Following Blitzstein’s murder, details began to emerge in the late 1990s outing Milano as a quasi-informant. “Flipper”, much like another member of ‘mob royalty’, former acting boss, Louis T. Dragna, had been interviewed by the FBI and had provided information related to members of the Los Angeles crime family. Notably, Milano identified his brother as the boss of family, Jimmy Caci as the only caporegime and was vehement in his identification of Louie Caruso as nothing more than a soldier in the organisation, additionally confirming ties between a limousine company (potentially Express Tours, where Milano had laundered money) and “the little guy”, when questioned by the FBI.

Milano also informed investigators of his relationship with his brother, who, categorised as a “vicious intriguer” by Gallo, had “said some bad things about him in the past”, indicating that things were not entirely amicable between the brothers. Of additional note is that Milano claimed the LA family had actually dissolved in the late 1980s (following the Fiato indictments) and that members of families from New York and New Jersey operated freely in California and Nevada, not paying tribute to Los Angeles.

Ultimately, despite his cooperation, Milano chose not to become a witness for the government and was sentenced to 21 months of prison time in 2000. Breakshot as well as a 2001 congressional hearing identified Tommy Gambino as Carmen Milano’s successor, though Gallo believed that a “rat” was still a better choice than the young Gambino, who was in his mid-20s when promoted.

Released from federal custody on the 27th of February, 2002, Carmen Joseph Milano would die little under 4 years later on January 3rd of 2006, at 76 years old, due to health complications. Kenji Gallo, in a blog entry, recounts how he had been contacted by someone in Las Vegas who informed him of Milano’s death but when calling a local news outlet, the reporter was not aware of his passing at all. Contacting the morgue, staff asked Gallo for a next of kin, indicating that not even Carmen’s brother was aware. Gallo passed on Pete’s details, effectively ending the saga of the Los Angeles family’s last real underboss.

“Maybe it’s because I’m not one of the gang, I don’t know. It’s not my cup of tea. I’m not from the fast lane, the Bruce Willises, that type of thing. I’m very boring.”

­– Carmen “Flipper” Milano, LA underboss, in a 1987 Los Angeles Times interview

The second lawyer to hold an administration spot in LA, Carmen Milano was one of the more interesting characters that made up Pete Milano’s mob and certainly was “one of the gang”, though your view may vary on if being a gangster was his “cup of tea”, given how he was, after all, a member of the Mickey Mouse Mafia.

Carmen “Flipper” Milano in his younger years