Family Affair

by Sam Giancana

  Joining the Calabrese crew in 1978, Tolomeo became Frankie Breeze’s point man on the crew’s behemoth-size loan-sharking business. At his peak, Tolomeo had over a hundred customers on juice, reaping the crew the benefit of huge interest payments on their original loans. These funds were collected on a weekly basis by the crew’s street heavies, Louie Bombacino and Terry Scalise.

  Five years into his career working for Calabrese, Tolomeo was accused of skimming profits from his numerous collection routes, not turning in full shares of the ever-thickening till. He was beaten severely for the indiscretion by Frank Calabrese himself, who broke his nose and several ribs while dealing out the punitive assault. He was also forced to sign over the title to his mother’s Elmwood Park home to Nick Calabrese’s father-in-law. Upset with the treatment he received, Philly Beans turned to the FBI and began providing information on the Calabrese crew, and by the mid-1990s, he had entered the witness protection program.

  Matt Russo was the owner of the crew’s headquarters, the nerve center of the city’s biggest loan-sharking racket, the M&R Auto and Truck Repair Service. He bought the business with startup money provided to him by Frank Calabrese, so Calabrese considered himself a silent partner. Behind on bank loan payments, Russo borrowed $20,000 in cash from his partner. He then got behind on the payments for his street loan and was quickly devoured by Calabrese’s predator-like instincts.

  Even though he was close friends and business partners with Frankie Breeze, he wasn’t spared the usual treatment. Always looking for quick-and-easy ways to line his pockets with cash, Calabrese decided to bust out Russo’s most lucrative asset, the auto repair business, which was his own headquarters. In fact, Frankie Breeze had been starting to exploit M&R even before Russo got into debt. including using it as a site for meetings and for cash distribution sessions.

  As a means of repaying his debt, Russo was instructed to begin filing false invoices for repair work never performed and eventually was forced to sell his home to Calabrese. Fearing for his safety, he fled to the FBI. Wired for sound, Russo began making what would end up being hundreds of hours of tape recordings of life in and around the ruthless Chinatown mob chief. The tapes would be devastating court evidence.

  “The instant we got Russo wired up and on the street, the case against Calabrese was sealed,” said Bourgeois. “He talked his way into the indictment. I don’t think he suspected that Russo was cooperating so he was more loose lipped in his presence. The information we got from Philly Beans Tolomeo got the investigation jump-started, but after Russo started to cooperate we had him cold.”

  The icing on the cake in the case being built against the Calabrese crew came when Louie “The Baker” Bombacino, a protégé of both Tolomeo and the late Louie Eboli who took Tolomeo’s place after his defection, ordered one of his street toughs to assault an undercover cop believed to be a recalcitrant customer. Then The Baker got arrested for attempted jury tampering. His blunders made it a slam dunk: Frank Calabrese, tough guy, killer, and Outfit mob chief, was falling. And fast.

  The indictment for what the government categorized as a multimillion-dollar loan-sharking operation came down in 1995, ensnaring the entire crew. Plea agreements followed, and guilty pleas were entered the following year for all four Calabrese men: Frank, Nick, Frank Jr., and Kurt.

  The Calabrese family shared Christmas dinner together in December 1996, where upon leaving for the night Nick gave Frank a rare kiss on the lips. Maybe he knew things were never going to be the same again. Maybe he just had too many cocktails at dinner and was just in an affectionate mood. Either way, it would be the last time the two brothers would ever see each other outside the confines of a federal courtroom.

  In early 1997, Frank and his kids were incarcerated in Milan, Michigan, and Nick was sent to do his sentence in Pekin, Illinois. Spending a lot of his time behind bars socializing with Outfit power James “Jimmy the Man” Marcello, who was serving a stretch for a racketeering conviction, Nick immediately began vocalizing his displeasure with the conditions under his brother’s regime. Apparently, he was also bothered by his brother’s treatment of his nephews, who Nick believed had been physically and emotional abused by their father.

  Marcello sensed that Calabrese might be a weak link. He worried that because Nick could tie him to the Spilotro brothers hit as well as possibly others, he would be personally vulnerable at the first inkling of Calabrese’s discontent. When scuttlebutt about the reopening of a previously unsolved gangland homicide that had the recent addition of physical evidence pointing to Nick reached Jimmy the Man, he was downright petrified.

  Jimmy tried to remedy his vulnerability by sending Nick Calabrese’s wife cash payments of $4,000 dollars per month via his contacts on the outside, specifically through his half-brother, Michael “Big Mickey” Marcello. In the end, it wouldn’t be enough. With the amount of physical evidence thrown in his face by the FBI, Nicky Breeze was in too tight of a corner. No amount of money could have bailed him out. The avalanche was coming down and Jimmy Marcello and Frankie Calabrese, were about to get crushed. Nick Calabrese was ready to sing like a canary and the FBI was waiting with open arms. Hello Operation Family Secrets!

  8.

  Chinatown

  The Twenty-Sixth Street Crew

  Both Frank and Nick Calabrese were members of the Twenty-sixth Street crew, one of The Outfit’s most notoriously ruthless and violent subfactions. Also known as the South Side crew and the Chinatown crew, the group had a rich and storied history in the city’s underworld.

  “The guys from Chinatown have always been the heavy hitters, the ones you went to when you needed some serious work done,” said former FBI agent Jack O’Rourke. “They have the most influence in local politics and almost all of the crew’s soldiers are deep in the trenches, not afraid to get their hands dirty. It’s a lunch pail, working-class group of criminals down there on Twenty-sixth Street. That’s the way they are now and that’s the way they’ve been forever.”

  The crew’s first capo, Bruno “The Bomber” Roti, dates all the way back to the days before the rule of Al Capone. Roti was one of Chicago’s original Black Hand extortionists—a racket that swept across major American cities in the early portion of the last century, threatening Italian and Sicilian immigrants in handwritten letters with physical harm if they did not immediately fork over money. He also became one of the inaugural batch of initiates under Capone when The Outfit was created in 1931.

  Getting his nickname The Bomber early on in his criminal career due to a propensity to blow up the cars and homes of those who refused to give into his demands in the Black Hand racket, Roti was named one of the crime family’s first territory bosses. He was given authority over the near South Side, which included the vice-filled Chinatown district at Twenty-sixth Street and Wentworth Avenue. Over the years, the crew became known for its deep ties in the local government and the people to come to if you needed a job with the city or a city-based contract. Roti’s son Fred became the alderman for the extremely influential First Ward and one-time First Ward political powers Pat Marcy and John D’Arco are rumored to have been made members of The Outfit. As a result of these ties, the crew developed into a hotbed of labor union infiltration. Roti’s family, friends, and criminal associates alike all benefited with jobs and perks. Reporting directly to The Outfit’s political fixer extraordinaire, Gus “Slim” Alex, Bruno Roti and the mob’s men from Twenty-sixth Street made life as smooth sailing and as hassle free as possible for Tony Accardo and his crime family.

  When Bruno Roti died in 1957, the reigns of the Twenty-sixth Street Crew fell to his son-in-law, Frank “Skids” Caruso Sr., who made a name for himself in the Chicago underworld by running one of the biggest sports wire services and horse-betting operations in the entire area. Caruso’s wire room was located at Twenty-second Street and Wentworth Avenue, right next door to a fire station. It was run by two of his top gambling lieutenants, Anthony “Tony B” Bova and Anthony “Blind Tony” Vinci,
and became a breeding ground for up-and-coming young South Siders and aspiring hoodlums, like Frank Calabrese, the La Pietra brothers, and Caruso’s own sons and nephews. If he wasn’t at the wire room, Skids could most times be found at the Bowery Lounge on Twenty-second Street. The Bowery was where Caruso and Gus Alex were known to hold court with their subordinates and collect tributes from their numerous rackets, which included gambling, juice loans, extortion, and jukebox and vending machine businesses.

  Caruso’s oldest son, Frank Jr., also known as “Toots,” “Tootsie,” or “Tootsie Babe,” was intent on following in his father’s footsteps. He started at a young age as a runner for his dad’s wire service. Soon, he graduated to making collections for the family loan-sharking and bookmaking businesses. And then, alongside one of The Outfit’s top burglars, Richard “Richie the Rat” Mara, he is alleged to have begun doing armed robberies, overnight heists, and home invasions.

  Being groomed to eventually take over his father’s South Side empire, Toots Caruso set up a headquarters at a restaurant he opened called The Hungry Hound, in the heart of Chinatown and used it as a base of operations for himself, his brothers, Bruno and Peter, and his first cousin, Leo. By the early 1980s, Toots was ensconced in the president’s chair of Local 6 of the Laborers International Union of North America, and was a delegate to the city’s district council. Toots’s younger brother Bruno would become president of Local 1001 of the County, Municipal Employees, and Foreman’s Union, in 1994 and shortly thereafter was made president of the entire Chicago District Council, before being ousted for his mob connections in 2003.

  As Skids Caruso began getting up in age during the 1970s, he started to prepare for the inevitable transition in leadership his crew was going to undergo in the coming years. With his son Toots still too young to become a capo, Skids tapped Angelo “The Hook” La Pietra, to take on the role on a temporary basis, as he primarily stood on the sidelines and offered counsel from semiretirement in Florida. La Pietra had come up under and was tutored in the ways of The Outfit by West Side crime boss Fiore “Fifi” Bucceri, before moving his own burgeoning vice empire south to Chinatown.

  After Skids Caruso died in 1983, La Pietra, sometimes called “The Bull,” took over as full-time capo of the crew, and his headquarters at the Italian-American Brotherhood social club became the epicenter of the area’s criminal commerce. Under La Pietra, Frank Calabrese, one of the Hook’s top protégés, built his loan-sharking operation up to become the biggest and most lucrative in the city. Calabrese put so much money into La Pietra’s pocket, that he and Nick ascended to the rank of the crew’s premiere enforcement team, collecting from the toughest debtors and being assigned the most important hit contracts.

  “Angelo La Pietra was a real pro,” said O’Rourke. “He was well versed on every aspect of being a gangster, and he made no bones about who he was. In the history of the South Side of Chicago not many wiseguys held more stature than La Pietra. He was small, only about five five, five six, but incredibly intimidating,. He carried himself with tremendous moxy. When he walked or drove through the neighborhood, everybody took notice. The Calabrese brothers learned everything they knew from him. Especially Frank, who tried to emulate him in every way possible.”

  IN the 1980s, the Chicago underworld saw growing profit margins due to a robust economy, but these were also tumultuous times for the Twenty-sixth Street Crew and The Outfit as a whole, in the form of a boatload of rats. Chinatown crew members Richie Mara, Charles “Guy” Bills, and Gerry Scarpelli as well as Outfit regulars Lenny Patrick, James “Jimmy the Panda” La Valley, William “B.J.” Jahoda, James “Jimmy the Duke” Basile, Joseph “Joe the Undertaker” Granata, and Ken “Tokyo Joe” Eto all turned on the mob, testifying against members of The Outfit in court.

  Without a doubt, the biggest blow dealt in the plethora of defections was that of Ken Eto, the most powerful Asian gangster to ever walk the streets of Chicago. Running a massive gambling empire for over twenty years out of the Golden 8 Ball Pool Room on Rush Street, Eto, who reported to North Side capo Vincent “Innocent Vince” Solano, made a fortune for himself and The Outfit by gaining a monopoly over the city’s Bolita racket—a policy lottery ran out of Asian and Hispanic neighborhoods. At his peak, Eto, known for his snazzy custom-made wardrobe, was clearing over $1 million per month in gambling profits.

  Although Eto didn’t work directly under Angelo La Pietra and his South Side crew, his decision to become a turncoat nonetheless threw a major wrench into the survival rates of a number of Chinatown criminals. Eto laid off a good deal of his gambling action to members of La Pietra’s crew and was partners with The Hook himself in several different weekly card and dice games around the area.

  When he flipped, his debriefing by the FBI led him to divulge a great deal about La Pietra and helped them strengthen their epic Las Vegas skim case, titled “Strawman II,” against him and fellow Outfit superpowers Joey Lombardo, Joey Aiuppa, and Jackie Cerone. His testimony in court in 1985 at the trial was one of the final nails in the proverbial coffin, aiding the government significantly in earning convictions of La Pietra, Lombardo, Aiuppa, and Cerone.

  Unlike most of the other defections, Eto’s was completely self-inflicted and could have easily been avoided. Arrested in a Melrose Park motel room in August 1980 and charged with running a large-scale gambling operation, Eto faced trial and the prospect of being incarcerated. This worried his superiors in The Outfit because they felt he was not mentally strong enough to do the possible time and could be tempted to turn against them. For The Outfit, these types of worries were quelled only by a murder contract. Thus, around Christmas 1982, one was issued for Eto by his captain, Vince Solano.

  On February 10, 1983, only a few months before his trial on gambling charges was set to begin, Eto was called to a meeting with fellow North Side crew members Joseph “Big Joe” Arnold and Joseph “Little Caesar” Di Varco at the Hideaway Bar and Lounge, a mob gathering post on Wabash Avenue. While at the meeting, he was informed that Solano wanted to have dinner with him that night and he was to pick up John Gatuso, a Chicago cop who moonlighted as an Outfit strong arm, and Jasper “Big Jay” Campise, a high-level North Side bookie and loan shark, on the way.

  Doing what he was told, Eto scooped up Gatuso and Campise in his Ford El Torino and made his way to the parking lot of the Montclare Theatre located on Grand Avenue, where he had been instructed they were to meet up with Solano. After turning off the engine, Gatuso, who was sitting in the backseat directly behind him, pulled out a 22-caliber pistol and put three shots into the back of Eto’s head. With Eto slumped over the steering wheel, Gatuso and Campise exited the vehicle and fled to a waiting automobile that whisked them away from the scene. Unfortunately for the two assassins and The Outfit in general, Eto was not dead. Somehow the bullets had only grazed his skull and once his assailants had left, he was able to get out of the car and walk to a nearby pharmacy and call for help.

  As soon as the FBI, got wind of what had happened and that Eto was in the intensive care unit at Northwestern Memorial Hospital, a fleet of agents ran to his bedside. Feeling betrayed by the mafia family he had worked so loyally on behalf of for over two decades, not to mention disrespected in lieu of the tens of millions of dollars he had made for them in his years of service, Eto had a lot to say.

  The following day, Gatuso and Campise were arrested and charged with attempted murder. Just over a week later, Solano, Arnold, and Di Varco were called in front of a grand jury convened to investigate the incident—all three pled the fifth.

  Freed on $1 million bail, the unlucky pair of mob executioners for some reason didn’t seem that worried about their own fate. When asked by an associate if he was afraid for his safety Jasper Campise is alleged to have responded, “No, they told me they don’t do that kind of stuff anymore.”

  He was wrong. They do. Five months later, on July 14, the heavily battered bodies of John Gatuso and Jasper Campise were found, stabbed and strangled to de
ath, in the trunk of a car in a west suburban parking lot.

  ANGELO La Pietra’s imprisonment from his conviction in the Strawman II case left a power void atop the Twenty-sixth street crew that was quickly filled by his younger brother, James “Jimmy the Lapper” La Pietra. Keeping The Hook’s rackets in check while he was away serving his time behind bars, Jimmy may not have been as feared as his elder sibling, but he was just as effective as a leader. The crew’s financial bottom line kept booming during his seven-year reign as capo. The Lapper passed away in 1993 and John “Johnny Apes” Monteleone was simultaneously bumped up to Chinatown captain and overall Family street boss. In order to effectively look after the Outfit’s daily affairs and oversee all the other syndicate capos, Monteleone broke his South Side crew into three sub-factions. According to a late ’90s Chicago Crime Commission report, he allegedly assigned command over them to Frank Calabrese, “Jimmy” Di Forti, and Michael “Handsome Mike” Talerico. A nephew of both La Pietra brothers, Talerico was only thirty-one years old when he is alleged to have receieved the promotion. Under Monteleone’s reign, the Chinatown crew expanded and took over the former crews in the south suburbs, Chicago Heights, and Northwest Indiana.

  Regaining his freedom in 1996 after serving ten years in prison, The Hook was immediately bumped up in The Outfit’s hierarchy to an “acting underboss” post that he would hold in the John Di Fronzo administration until his death in 1999.

  Monteleone died in 2001 and it is alleged that Chinatown’s prodigal son, Toots Caruso, then assumed the throne his father and grandfather once held. Officially named captain over the South Side in 2002, Caruso is currently the youngest of all The Outfit’s territory bosses. He quit his position on the city’s LIUNA District Council in the early 1990s due to pressure from the government; when he is alleged to have become a capo, he was the assistant director of the union’s board of trustees and its nearly $800 million pension fund. His reputed promotion to crew boss, however, brought unwanted attention from law enforcement, and in 2003 a giant purge of organized labor in Chicago brought an end to the union careers of the entire Caruso family—Toots, his brother Bruno, and his cousin Leo were each ousted from their positions within the LIUNA when all the union’s Windy City locals went into court-ordered trusteeship.