Shadow Life – The Roman Files
Season 3 Ep. 7
The mentor
Slowly walking down the aisle, Roman lifted his head to peer into the open casket that sat at the end of the viewing room at the funeral home, the small elderly man had lived into his 90s. Which was unbelievable as it was true…
Even when he was alive, the man was barely 5 feet tall, and when Roman gazed upon his old mentor - he looked tinier still.
He was shriveled, like a dried out prune… the size of a boy, but with wispy old-man's hair and those folded, wrinkled hands. A cross was pinned to the inner lining of the coffin, what a joke Roman thought, fore he knew his friend only believed in one thing, one day you’re alive, the next you’re dead. That’s all there was to it.
Roman couldn’t imagine how the old man died naturally in his sleep like a fuckin’ baby, but goddamn if he didn’t, Roman recalled one of his most favorite sayings; he’d rather be lucky than smart… and to think that Marshall Caifano would get to die a natural death is pretty fucking lucky.
Because in life Roamn’s elderly mentor, was said to favor the shotgun and the car bomb, as one of the most notorious hit men in the history of the Chicago Outfit.
Caifano arrived in Chicago back in the 1920s and was brought to the attention of Paul Ricca, the real boss.
The low-key Ricca was extremely smart. He had everybody in his pocket, cops on the take, politicians and judges on the payroll, just to make sure of things, and killers to make real sure things got taken care of.
They're not your typical gangster stereotypes everyone sees on tv or at the movies
No, these are the real deal, un-assuming… soft-spoken… not the big tuff guys you might see along Rush Street on Friday nights. These guys, are normally small in stature, un-assuming… they favor the shadows and most importantly, the step as lightly as a cat in the alley…
Then and now, it’s the small guys that do what the FBI calls "the heavy work."
Caifano and his pal Vincent "The Saint" were both small men, soft spoken and appeared as harmless as a housecat if you didn’t know any better.
"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 unit.
"He was a close friend of Tony's, doing as much heavy work as Accardo or Sam Giancana or anybody for that matter.
In the late 1940s Caifano was sent to Los Angeles, around the time Ben "Bugsy" Siegel was building Las Vegas into a gambling mecca.
Gus Russo's book about the Chicago Outfit, properly titled "The Outfit," stated that Siegel was at his Beverly Hills home with a Caifano associate; Alan Smiley when another man walked through the patio door and shot bugsy twice in the head and two in the chest.
Twenty minutes later, Gus Greenbaum, the Outfit's accountant, arrived at Siegel's Hotel in Vegas and announced, "We're taking over."
Hollywood movies like "The Godfather" make it appear as if New York gangsters had finished Siegel, but then Chicago has a Hollywood reach, and Hollywood never made a movie about Paul Ricca.
In 1943 Caifano's friend Nick Circella faced an extortion trial. (according to the newspapers), there was a witness that was about to cooperate with federal prosecutors. A burned, battered and ice-picked body was later found, and the prosecutions star witness had disappeared.
Caifano was a prime suspect, but the case was never solved, he was also suspected 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 a sandwich shop on West Grand Avenue.
In the 1950s the Outfit moved in on the street lottery--and tried to kidnap policy king Theo Roe. But Caifano's brother was killed during the botched kidnapping attempt.
Roe pleaded self-defense. A year later, Roe was murdered by two men with shotguns. Caifano and Giancana were never charged.
In 1964, though, Caifano was convicted of trying to extort $60,000 from Indiana oilman Ray Ryan, who had testified against him. When Caifano was released from prison in the 1970s, Ryan wanted to pay him $1 million in restitution ya know, sort of smooth the rough edges of any hurt feelings from doing time…
According to a federal authorities, Caifano told street boss Joey Lombardo, "Let's take the million and kill him anyway."
On Oct. 18, 1977 Ryan walked out the Evansville Health spa and climbed into his Lincoln continental, turned the key in the ignition… in a mere micro-scecond , the electrical current flowed from the starter down to the blasting cap attached on the 3 sticks of dynamite taped to the cars catalytic converter –
Ray never felt a thing. The compression pulsated through his body, a shockwave of unleashed power of Einsteins famous equation E = Mc squared…
Ray Ryan had punched his ticket.
Caifano was questioned by authorities but never charged. He had an airtight alibi.
The cops hadn’t paid much attention to the young kid hanging in the back of the crowd of onlookers, just a fair haired all American looking kid, small, un-assuming… staring out from the shadows. Watching.
Then a few years later, the Reputed Chicago Mafia associate Joseph Testa, age 53, who had escaped three previous bomb attacks, authorities suspected Caifano was involved in due to the fact that Caifano alleged that Testa owed him $2 million. Testa didn’t see it that way.
But on a hot, humid day in July of 1981, the debt was paid regardless…
As the red ball south florida sun glared off the windshield of Testas car as he pulled out of a parking space at the Tama-rack Country Club in Oakland Park, Ft. Lauderdale Florida
Testas car exploded into a fireball, the bomb squad said it was most likely a remote control device type- bomb, planted under the driver's side of the car, . Testa was thrown 100 feet. His right leg and part of his right arm were blown off. It took him two days to die in the hospital. The case was never solved, but police theorize the killing was mob related.
Federal prosecutors believe Caifano planned it from prison.
1977 – Evansville “Little Chicago”
Newspaper article from the Evansville Courier-Times
What many residents old enough to remember on that fall day on Oct. 18, 1977, will recall is the day our sheltered city experienced its brush with the Mob. A car bomb exploded outside of Olympia Health Spa (on Bellemeade Avenue just east of Green River Road) shortly after 1 p.m., damaging a nearby apartment building, hurling debris nearly a football field away, knocking out power on the Southeast Side of town, and killing the Lincoln Continental Mark V’s occupant, local oilman Ray Ryan.
Ryan, described by some as a “larger than life character,” traveled often and lived the lifestyle of the rich and deceptive, the former earning him friendships with some of Hollywood’s greatest star power of the day — Dean Martin, Frank Sinatra, Bing Crosby, Bob Hope — and the latter connecting him with gangsters such as Frank Costello and Frank Erickson. These relationships were further strengthened through his partnership with actor William Holden to develop the Mount Kenya Safari Club in east Africa, a playground for the rich and famous and high-ranking members of organized crime.
Marshall Caifano was convicted of extorting $60,000 from Ryan, who testified against him.[7] The conviction was upheld in 1966, and Caifano was sentenced to 10 years in prison.
When Caifano was released from prison in the 1970s, Ryan reportedly offered him $1 million in restitution; however, on October 18, 1977, Ryan was killed.
Roman met Caifano while he was working on his grandfather’s horse farm in Georgetown, Kentucky, well, not exactly his pop pops farm, but a thoroughbred racing horse farm that his pop pop managed for a wealthy gentleman from Chicago. Marshall Caifano, loved all things that had to do with gambling, especially horse racing, and as it turned out, he was also a high ranking member of the Chicago Outfit.
Roman was enthralled and hung on the older mans every word and the stories he told Roman while they watched the horses train with Romans grandfather, another Italian immigrant from the old country as well….
He told Roman all about what it was like back in the hey day of Vegas, Roman had never been but only seen images on the tv, that was enough to bloom images in his young fertile mind of the glory days of the mob…. Roman recalled having posters on his wall of his bedroom of the mafia boss, Al Capone, John Dillinger and Baby Face Nelson among a few… when other kids had David Cassidy, Farrah Fawcett, or Led Zeppelin posters on theirs. Not that there was anything wrong with that Farrah poster, God only knows how many times he wanked off to that poster….
Caifano changed his name to John Marshall when he moved to Las Vegas, where he was The Outfit's representative or capo over this area.
During the mid-1920s, Caifano joined the 42 Gang, a Chicago street gang, with future Outfit members such as Salvatore "Momo" Giancana.
By 1929, Caifano's rap sheet included convictions for burglary, extortion, larceny, and interstate fraud. As he matured, Caifano followed other 42 Gang members into The Outfit, which was run by none other than legendary mob boss Al Capone.
Caifano was suspected in about ten unsolved homicides, including those of disgraced Cook County sheriff's investigator and a suspected Outfit informant and oil tycoon Raymond J. Ryan.
Following the death of his brother, "Fat Lennie" Caifano, in 1951, Caifano was made overseer of mob-controlled casinos in Las Vegas.
Caifano’s wife, named Darlene, who was from outside of Louisville, Kentucky.
It is said that Caifano traded the "blonde-haired bomb shell" to the Godfather of the Chicago Mob, Sam Giancana, a childhood friend of Caifano's, for the "Don" chair of Las Vegas.
Caifano was a suspect in ten or more Mafia slayings during this time.
including the 1977 murder of Ray Ryan.
Now to the rest of the story…
Caifano was intrigued by this kid, who appeared as a fresh face all-american boy who should be playing baseball not hanging out with old gangsters like himself, but the kid was relentless, he absorbed every word like it was the juiciest bite of a steak…
Caifano and Roman’s pop pop spoke about romans situation, why he lived with him during the summer and worked the farm, Evidently, the police were looking at Roman for a string of burglaries and robberies throughout the tri state area, Caifano had even heard the kid had stolen a dirtbike and rode the damn thing through the halls of his junior high…
Romans pop pop had shared a few bits of romans past as well, the trouble he had in school being dyslexic, being the son of an out of the closet gay man 1970’s small midwestern town full of narrow minded folks that liked a heaping spoonful of prejudice with their roast beef and jesus gravy.
No life hadn’t been easy for roman and every now and then it just flat out reared up and kicked the ever living shit outta him.
Pop Pop told Caifano about the time Roman was prolly in 7th or 8th grade…
How he’s been set upon by an escaped mental patient… no shit, a goddamn bonafide mental patient had escaped a psych ward, some ex army vet suffering from ptsd or some shit, maybe he had already been fucked in the head before Nam, who knows, but this vet comes back home and starts smacking his wife and kids around, just the sort of low key crap the cops don’t want any part of right?
The guys has a son, romans age, goes to school with him and everything, one day, roman and a couple of buddies are fucking around in front of this ex-army vets house and little did anyone know he had slipped a restraining order and was hiding out inside… the vets son doesn’t even know his old man is inside and a few of the boys go in for something to drink, snacks whatever, you know how kids are… the vet bum rushed them, and picks out roman as the center of his attention ya know, starts slapping him around, one thing leads to another and it turns into a full on brawl, I mean blood gets spilled, knives, baseball bat, the whole 9 yards right…
Roman gets messed up pretty good, the cops get involved, the guys goes back into the nuthouse, just everything gets sideways… romans parents are going through a divorce, school is a living hell for the kid… where to turn and run right?
So me and his grandma take him in and try to keep him outta trouble, he’s a good kid at heart… but there’s something else, something dark in him, so much anger inside the poor kid, sometimes he seems to be drowning in it, an ocean of anger at what life has dealt him so far… I do what I can but… just sayin, kids got issues.
fucking hell, caifano thought, this kids seen more hard times than most men he knows… and he’s only 14…
Caifano and Roman spent weeks in each others company, together talking about the outfit, playing checkers, swapping war stories from their childhood… Roman had even shared with this new mentor figure what had happened between him and his own father.
But also, Caifano had the first inkling of an idea that the kid might be just what he needed at that precise moment in his life, the perfect instrument to deliver a white hot serving of revenge, the plan was beginning to form how he might be able to show the kid the ropes, teach him some life lessons and give the kid an outlet for all that anger he was drowning in… yes, yes, it was all beginning to come together.
Caifano snapped out of his daydream and looked over at the kid wearing him out on a game of checkers… “hey kid, Caifano spoke softly… what do you know ‘bout dynamite?”