As just a teenager, deceased Detroit mob captain Matthew (Mike the Enforcer) Rubino pulled the trigger in one of the Motor City’s most infamous gangland assassinations and as reward for a job well done was inducted into the mafia by legendary Midwest dons Joseph (Joe Uno) Zerilli and William (Black Bill) Tocco the very next day, according to freshly-unearthed FBI records by author and historian Daniel Waugh. The records, citing a well-placed confidential informant, claim a then-18 year old Rubino killed West Side crime lord Chester (Big Chet) LaMare inside LaMare’s own mansion on February 6, 1931, which brought an end to the so-called Crosstown Mob War and birthed the Tocco-Zerilli crime family and modern-day Detroit mafia.

Mike Rubino died at 62 of a heart attack on August 7, 1972 while in the middle of serving a federal prison sentence for tax evasion in Leavenworth, Kansas. He had been considered a capo in the Tocco-Zerilli clan since the late 1940s, taking over a crew formerly ran by Detroit mob founding father Peter (Horseface Pete) Licavoli, who departed Michigan and relocated to the west coast and a state-of-the-art palatial ranch in Arizona.

Licavoli came to Detroit from St. Louis in the 1920s and established a bootlegging empire known as the River Gang at the height of Prohibition. Early in the following decade, he teamed with Joe Zerilli and Black Bill Tocco and their East Side Gang to square off with Big Chet LaMare on the West Side for control of the city’s underworld in a bloody street war that claimed more than a dozen lives.

Rubino spawned from West Side Gang roots and his father and two older brothers fell victim to a previous, significantly smaller crosstown conflict in the summer and fall of 1926. Per the FBI records obtained by Waugh, Rubino’s dad and siblings were killed by Zerilli and Tocco’s top hit man Pietro (Machine Gun Pete) Corrado. Zerilli, Tocco and Corrado were all brothers-in-law.

After his father’s murder, Rubino moved in with LaMare lieutenant Joseph (Moonlight Joe) Marino and subsequently became Marino’s driver and bodyguard before his 16th birthday. The rough-and-tumble Rubino became acquainted with the Detroit Police Department at an early age – he got hauled into his local police precinct as a mere 7-year old for severely beating a rival paper boy.

Moonlight Joe Marino was responsible for unloading LaMare’s smuggled booze from Canada, which he would do late at night under the light of the moon (hence his nickname). By the time Mike Rubino reached 18 he had almost a dozen arrests on his police sheet. He was questioned by police in a pair of high-profile mob hits in the months leading up to the Big Chet LaMare assassination, not to mention being detained by authorities in the wake of his mentor Marino’s suspicious death.

In the summer of 1930, Rubino was brought in for questioning in the murder of Detroit radio personality Jerry Buckley inside the lobby of the LaSalle Hotel. On January 2, 1931, he was arrested for trying to kill Detroit Police Inspector Henry Garvin, the head of the department’s mob squad, in a drive-by shooting. The charges against him in the Garvin shooting were eventually dismissed.

Marino popped up dead in his own house on September 27, 1930 and Rubino was present and shipped off to the police precinct for questioning until Marino’s son came forth and told detectives he had accidentally shot his dad in the den. Whether Marino’s offspring was being truthful or was forced into coming forward to take the rap for Rubino is still unclear today.

Around this same time, Big Chet LaMare’s second-in-command Angelo (The Chairman) Meli defected to the East Side Gang. Meli was a labor-racketeering whiz, having arranged a number of lucrative vending contracts with automobile magnate Henry Ford and the Ford Motor Company for LaMare and the West Side Gang in the years preceding his departure.

So what prompted Meli to jump ship from Big Chet’s camp?

Just weeks before Buckley was killed for his anti-mafia and political-corruption rants on his nightly radio broadcast (despite his own gangland affiliations), LaMare orchestrated the Vernor Highway Fish Market Massacre, the machine-gun slayings of two East Side Prohibition powers, Gaspare (The Peacemaker) Milazzo and Salvatore (Sasha) Parrino. Milazzo and Parino were lured to their death under the pretense of attending a peace conference. Sent from New York, Milazzo was acting as Joe Zerilli and Black Bill Tocco’s primary advisor during the war against LaMare and his West Siders.

However, Milazzo and his bodyguard Parrino weren’t LaMare’s intended targets. Big Chet had wanted to bump off Zerilli and Tocco. When he wasn’t successful, Meli, always the pragmatist, saw the writing on the wall. Knowing LaMare had made his play and lost, Meli bolted for the East Side.

Mike Rubino would soon join him. He was recruited east by Meli and Pete Licavoli, already in the process himself of merging his River Gang with Zerilli and Tocco’s East Side Gang. Meli and Licavoli set up a meeting for the trigger-happy teenage Rubino with Joe Uno and Black Bill to see if they could work out an arrangement. They did.

Zerilli and Tocco offered to “make” Rubino into the mafia immediately if he killed LaMare for them in exchange for Rubino agreeing to not take vengeance on Machine Gun Pete Corrado for Corrado’s involvement in the murder of his father and two brothers five years before, according to the federal files Waugh found. Rubino agreed.

Besides Meli and Rubino, LaMare’s own wife, bodyguard and right-hand man Joe Amico and go-to enforcer Elmer Macklin, a former member of St. Louis’ Egan’s Rats Gang, betrayed him and conspired with the Eastsiders in his assassination. LaMare’s young bride left the LaMare estate in the early-evening of February 6, 1931 and Macklin and Amico told the armed guards at the entrance of the estate to stand down and go home, leaving the front door unlocked for an assailant to enter, per a number of police informants. Rubino walked into LaMare’s mansion unabated that night, went into the kitchen where Big Chet was having coffee with Amico and Macklin and shot him dead, according to the informant in Waugh’s records. Rubino was officially inducted into the mafia the next day in a ceremony presided over by Zerilli and Tocco, while being sponsored by Licavoli and Meli.

Zerilli, Tocco, Amico, Macklin and LaMare’s wife were all arrested the week of the LaMare hit, with Amico and Macklin eventually going on trial on first-degree homicide charges and being acquitted. Upon LaMare’s murder, Zerilli and Tocco brought all the city’s bootlegging regimes, including the remnants of the LaMare-controlled Westside group, Licavoli’s River Gang, the East Side-affiliated Downriver Gang, based out of Wyandotte, and the iconic all-Jewish Purple Gang under a single banner known locally as “The Combination” or “The Partnership.”

Zerilli and Tocco ruled the mafia in Detroit side-by-side and unchallenged for the next four and a half decades, dying peacefully in 1977 and 1972, respectively. Angelo Meli and Pete Licavoli did the same in 1969 and 1984, respectively. In 2015, author and historian Dr. James Buccellato, discovered LaMare’s status as a confidential federal informant amongst a trove of U.S. Government files housed in Maryland.

Macklin and Amico were the gunmen in the Vernor Highway Fish Market Massacre. Amico vanished in 1937. Meli and Licavoli took over and split LaMare’s rackets following his death.

Rubino was assigned to Licavoli’s crew and became his main muscle until he assumed command of the crew in around 1946 when Licavoli left Motown for the Phoenix area. He had done five years in federal prison in the 1930s for counterfeiting and in early 1941 was shipped back to the pen for narcotics trafficking in a case Meli, by that time, the Detroit mob’s underboss, was named as an unindicted co-conspirator. By the end of the summer of 1942, Rubino had returned to the streets and was doing Licavoli’s bidding again.

Case in point: the Eddie Sarkesian situation.

The 29-year old Sarkesian drew Licavoli’s ire by robbing a series of his gambling houses and placed Rubino on the job of eliminating the problem. Sarkesian was slain walking in downtown Detroit on Cadillac Street on August 16, 1944, shot five times in the head, face and neck at close range. Rubino and former Purple Ganger Morris Raider were arrested for Sarkesian’s murder and held for two weeks before being released and charges dismissed when witnesses refused to testify against them.

The very next year Rubino used his reputed participation in Sarkesian’s execution to extort a local gas station owner.

“You better pay up or you’ll get what Sarkesian got,” he told the man.

A majority of Rubino’s further legal hassles were with the IRS. He was busted for tax evasion in 1955 and then again in 1968 and was sentenced to federal prison terms in both, the latter of which he’d never make it back to the Motor City from. His 1955 arrest stemmed from his ownership of the Navaho Building downtown and a pair of jukebox distribution businesses (Moss and Chester Music) with fellow Detroit mob capo Salvatore (Sammy Lou) Lucido and the majority stock holding in the Torosian Oil Company with then up-and-comer and future crime family consigliere Michael (Big Mike) Polizzi, a gangland wunderkind with an accounting degree from Syracuse University.

Rubino owned large amounts of real estate as well. Throughout the 1950s and 1960s, he was known to often hold court at his Double D Horse Ranch.

*Daniel Waugh (Off Color: The Violent History of Detroit’s Purple Gang, Egan’s Rats) is an author and historian who focuses on early American mob activity in Detroit and St. Louis.

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